1-9 A-D E-G H-M N-P Q-S T-Z

D-LIMONENE

D LIMONENE

 

CAS NO: 5989-27-5
EC Numarası: 227-813-5

 

 

synonyms:
(+)-(R)-4-isopropenyl-1-methylcyclohexene;(+)-limonene;(-)-limonene;(4R)-1-methyl-4-(1-methylethenyl)cyclohexene;(4S)-1-methyl-4-isopropenylcyclohex-1-ene;(D)-limonene;(R)-(+)-limonene;(R)-4-isopropenyl-1-methylcyclohexene;1-methyl-4-(1-methylethenyl)cyclohexene;4-mentha-1,8-diene;AISA 5203-L (+)limonene;cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-;d-limonene;dipentene;limonene;limonene, (+)-;limonene, (+-)-isomer;limonene, (R)-isomer;limonene, (S)-isomer;D-Limonene;(+)-Limonene;5989-27-5;(R)-(+)-Limonene;(+)-(4R)-Limonene;(+)-carvene;Citrene;(+)-p-Mentha-1,8-diene;(4R)-Limonene;(+)-Dipentene;Carvene;Glidesafe;Glidsafe;Kautschiin;Refchole;(+)-R-Limonene;D-(+)-Limonene;(R)-p-Mentha-1,8-diene;D-Limonen;(R)-4-Isopropenyl-1-methyl-1-cyclohexene;d-p-Mentha-1,8-diene;(D)-Limonene;(R)-Limonene;Limonene, D-;Biogenic SE 374;(+)-alpha-Limonene;d-Limonene (natural);d-Limoneno [Spanish];(+)-(R)-Limonene;(+)-4-Isopropenyl-1-methylcyclohexene;Hemo-sol;(4R)-(+)-Limonene;(R)-(+)-p-Mentha-1,8-diene;UNII-GFD7C86Q1W;Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-;(R)-1-Methyl-4-(1-methylethenyl)cyclohexene;CCRIS 671;FEMA No. 2633;EC 7;(4R)-4-isopropenyl-1-methylcyclohexene;HSDB 4186;D-1,8-p-Menthadiene;NCI-C55572;EINECS 227-813-5;p-Mentha-1,8-diene, (R)-(+)-;Limonene, (+)-;(+)-1,8-para-Menthadiene;AI3-15191;CHEBI:15382;1-Methyl-4-(1-methylethenyl)cyclohexene, (R)-;(R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene;r-(+)-limonene;(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene;MFCD00062991;SBB055254;(4R)-1-methyl-4-prop-1-en-2-ylcyclohexene;(4R)-1-methyl-4-(1-methylethenyl)cyclohexene;(+)-Limonene, stabilized with 0.03% tocopherol;Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (theta)-;d-Limoneno;Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-;D-limonene [JAN];Citrus stripper oil;Terpenes and Terpenoids, limonene fraction;Sulfate turpentine, distilled;Dextro-limonene;d limonene;citre ne;Racemic limonene;65996-98-7;EINECS 266-034-5;(+) Limonene;limonene, (R)-isomer;D-Limonene Reagent Grade;DSSTox_CID_778;AC1L9A6P;DSSTox_RID_75785;GFD7C86Q1W;DSSTox_GSID_20778;4betaH-p-mentha-1,8-diene;CHEMBL449062;DTXSID1020778;HMDB04321;(R)-(+)-Limonene, 95%;(R)-(+)-Limonene, 97%;MolPort-002-507-206;XMGQYMWWDOXHJM-JTQLQIEISA-N;ZINC967513;CS-M3273;(R)-(+)-Limonene, >=93%;Tox21_200400;6458AE;ZINC00967513;AKOS015899935;LMPR0102090013;LS-1427;NE11118;(R)-(+)-Limonene, analytical standard;NCGC00248591-01;NCGC00257954-01;(4R)-4-isopropenyl-1-methyl-cyclohexene;AJ-24525;AK117763;DR000133;OR115854;SC-65387;ZB015452;CAS-5989-27-5;(4R)-1-methyl-4-isopropenylcyclohex-1-ene;(R)-(+)-4-Isopropenyl-1-methylcyclohexene;FT-0603053;L0047;L0105;C06099;(4R)-1-methyl-4-(1-methylvinyl)cyclohex-1-ene;J-502148;W-105295,I14-11275;(R)-(+)-Limonene, primary pharmaceutical reference standard;CYCLOHEXENE; 1-METHYL-4-(1-METHYLETHENYL)-; (R)-;UNII-9MC3I34447 component XMGQYMWWDOXHJM-JTQLQIEISA-N;(R)-(+)-Limonene, purum, >=96.0% (sum of enantiomers, GC);(R)-(+)-Limonene, technical, ~90% (sum of enantiomers, GC);1051930-86-9;7705-13-7;94765-75-0;95327-98-3;R-limonene;orange peel oil;citrus peel oil;citrene;Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-; p-Mentha-1,8-diene, (R)-(+)-; (+)-(R)-Limonene; (+)-(4R)-Limonene; (+)-p-Mentha-1,8-diene; (+)-Limonene; (R)-(+)-Limonene; Carvene; D-(+)-Limonene; Limonene, (D)-; Limonene, (+)-; (R)-1-methyl-4-(1-methylethenyl)cyclohexene; Dextro-limonene; (R)-4-Isopropenyl-1-methyl-1-cyclohexene; 4-Isopropenyl-1-methyl-1-cyclohexene-, (R)-; (R)-Limonene; (+)-Dipentene; (4R)-(+)-Limonene; (4R)-Limonene; (R)-(+)-p-Mentha-1,8-diene; (R)-p-Mentha-1,8-diene; Biogenic SE 374; Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-; EC 7; Glidesafe; Glidsafe; Refchole;carvene;D-citrene;(+)-limonene;(+)-(4R)-limonene;(+)-alpha-limonene;(+)-R- limonene;(4R)-(+)-limonene;(R)-(+)-limonene;citrus D-limonene;D-limonene;D'limonene;D'limonene;D'limonene (high purity, low odor);D-limonene citreatt;limonene D pure;limonene dextro redistilled;D-limonene high purity low odor;D-limonene natural;D'limonene natural;dextro-limonene natural;D-limonene P&F;limonene R+ SP natural;limonene R+ ST;D-limonene Rectified;dextro-limonene redistilled;(+)-p- mentha-1,8-diene;(+)-para- mentha-1,8-diene;(R)-(+)-para- mentha-1,8-diene;D-para- mentha-1,8-diene;dextro-para- mentha-1,8-diene;(+)-1,8-para- menthadiene;1,8 9-p- menthadiene;1,8 9-para- menthadiene;(R)-1- methyl-4-(1-methyl ethenyl) cyclohexene;(R)-1- methyl-4-(1-methyl vinyl) cyclohexene;(R)-1- methyl-4-(1-methylethenyl)cyclohexene;(R)-1- methyl-4-(1-methylvinyl)cyclohexene;(R)-1- methyl-4-isopropenyl-1-cyclohexene;(4R)-1- methyl-4-prop-1-en-2-ylcyclohexene;(+)-4-iso propenyl-1-methyl cyclohexene;4-iso propenyl-1-methyl cyclohexene;(+)-4-iso propenyl-1-methylcyclohexene;4-iso propenyl-1-methylcyclohexene;(+)-ALPHA-LIMONENE;BIOGENIC SE 374;CARVENE;(+)-CARVENE;CITRENE;CYCLOHEXENE, 1-METHYL-4-(1-METHYLETHENYL)-, (R)-;D-(+)-LIMONENE;D-LIMONENE;D-P-MENTHA-1,8-DIENE;(+)-DIPENTENE;EC 7;GLIDESAFE;GLIDSAFE;(+)-4-ISOPROPENYL-1-METHYLCYCLOHEXENE;(+)-LIMONENE;LIMONENE, (+)-;NCI-C55572;P-MENTHA-1,8-DIENE;(+)-P-MENTHA-1,8-DIENE;P-MENTHA-1,8-DIENE, (R)-(+)-;(R)-(+)-LIMONENE;(4R)-(+)-LIMONENE;(R)-(+)-P-MENTHA-1,8-DIENE;(R)-1-METHYL-4-(1-METHYLETHENYL)CYCLOHEXENE;(R)-4-ISOPROPENYL-1-METHYL-1-CYCLOHEXENE;(R)-LIMONENE;(+)-(R)-LIMONENE;(+)-(4R)-LIMONENE;(R)-P-MENTHA-1,8-DIENE;(+)-R-LIMONENE;4R-LIMONENE;REFCHOLE;d-p-MENTHA-1,8-DIENE; 4-ISOPROPENYL-1-METHYL-CYCLOHEXENE; 1-METHYL-4- (1-METHYLETHENYL) CYCLOHEXENE;(-)-(S)-Limonene;(-)-(4S)-Limonene;(-)-Limonene;(4S)-1-Methyl-4-isopropenylcyclohex-1-ene;(4S)-4-Isopropenyl-1-methylcyclohexene;(S)-(-)-P-Mentha-1,8-diene;(S)-1-Methyl-4-(1-methylethenyl)cyclohexene;(S)-P-Mentha-1,8-diene;4AlphaH-P-mentha-1,8-diene;L-Limonen;L-Limonene;4-Isopropenyl-1-methyl-1-cyclohexene;Limonene;(+)-Limonene;AISA 5203-L (+)limonene;Dipentene;1-Methyl-4-(1-methylethenyl)cyclohexene;Limonene, (+-)-isomer;(D)-Limonene;4-Mentha-1,8-diene;Limonene, (S)-isomer;Limonene, (R)-isomer;(+)-Dipentene; (R)-4-isopropenyl-1-methyl-1-cyclohexene; D-limonene;d-(+)-limonene; D-(+)-limonene; (+)-limonene; (+)-?-limonene; (+)-(R)-limonene;(+)-(4R)-limonene; (R)-limonene; (R)-(+)-limonene; (4R)-(+)-limonene; (+)-paramentha-1,8-diene;(R)-p-mentha-1,8-diene; (R)-(+)-para-mentha-1,8-diene;carvene : (+)- limonene : (+)-(4R)- limonene : (+)-alpha- limonene : (+)-R- limonene : (4R)-(+)- limonene : (R)-(+)- limonene : (+)-para- mentha-1,8-diene : (R)-(+)-para- mentha-1,8-diene : dextro-para- mentha-1,8-diene : (+)-1,8-para- menthadiene : 1,8 9-para- menthadiene : (R)-1- methyl-4-(1-methyl ethenyl) cyclohexene : (R)-1- methyl-4-(1-methyl vinyl) cyclohexene : (R)-1- methyl-4-isopropenyl-1-cyclohexene : (4R)-1- methyl-4-prop-1-en-2-ylcyclohexene : (+)-4-iso propenyl-1-methyl cyclohexene : 4-iso propenyl-1-methyl cyclohexene : Berje : dextro-Limonene : Berje : dextro-Limonene Redistilled : Citrus and Allied Essences : D'Limonene : Citrus and Allied Essences : D'Limonene (high purity, low odor) : Fleurchem : dextro-limonene natural : Fleurchem : dextro-limonene : Global Essence : dextro-LIMONENE : Moellhausen : limonene R+ SP 95pc min. natural kosher;Terpene Hydrocarbons NOS;Orange oil, terpenes;Terpenes and terpenoids, orange oil;Sweet orange, peel, tincture;Orange, sweet, extract;Limonene-D;1-methyl-4-(1-methylethenyl)cyclohexene, (R); l-Limonene; d-Limonene; dl-Limonene; Dipentene; Acintene DP; Cinene; Dipanol; Unitene; 1-methyl-4-isopropentyl-1-cyclohexene ;d-Limonene;(+)-Limonene;(+)-(R)-Limonene;(+)-(4R)-Limonene;LEMOSOL;POLY/CLEAR SOLVENT;(+)-(4R)-Limonene;(+)-1,8-p-menthadiene,(R)-(+)-limonene;(+)-4-isopropenyl-1-methylcyclohexene;(+)-limonen;(4R)-(+)-limonene;(gamma)-Carvene;(R)-(+)-1-methyl-4-(1-methylethenyl)cyclohexene,(r)-(+)-p-mentha-8-diene;(R)-1-methyl-4-(1-methylethenyl)cyclohexene;(r)-cyclohexen;(theta)-cyclohexen;1-methyl-4-(1-methylethenyl)-,(R)-Cyclohexene;4-isopropenyl-1-methyl-cyclohexen;4-isopropenyl-1-methylcyclohexene;citrene;Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-;cyclohexene,1-methyl-4-(1-methylethenyl)-,(R)-;Dextro-limonene;Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-; p-Mentha-1,8-diene, (R)-(+)-; (+)-(R)-Limonene; (+)-(4R)-Limonene; (+)-p-Mentha-1,8-diene; (+)-Limonene; (R)-(+)-Limonene; Carvene; D-(+)-Limonene; Limonene, (D)-; Limonene, (+)-; (R)-1-methyl-4-(1-methylethenyl)cyclohexene; Dextro-limonene; (R)-4-Isopropenyl-1-methyl-1-cyclohexene; 4-Isopropenyl-1-methyl-1-cyclohexene-, (R)-; (R)-Limonene; (+)-Dipentene; (4R)-(+)-Limonene; (4R)-Limonene; (R)-(+)-p-Mentha-1,8-diene; (R)-p-Mentha-1,8-diene; Biogenic SE 374; Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-; EC 7; Glidesafe; Glidsafe; Refchole;(+)-p-Mentha-1,8-diene; (+)-?-Limonene; (4R)-(+)-Limonene; (4R)-1-Methyl-4-(1-methylethenyl)cyclohexene; (4R)-Limonene; (R)-(+)-Limonene; (R)-(+)-p-Mentha-1,8-diene; (R)-4-Isopropenyl-1-methyl-1-cyclohexene; (R)-Limonene; (R)-p-Mentha-1,8-diene; 1-Methyl-4-prop-1-en-2-yl-cyclohexene; Bio Clear; Biogenic SE 374; Carvene; Clearene; D-(+)-Limonene; D-Limonene; EC 7; Fruits Dry; Glidesafe; Glidsafe; Histo-Clear; HistoSolve X; Limonene, (+)-; Master Clear; NK 1100; Refchole; Safsolv; Woody River 8; d-(+)-Limonene; d-Limonene; (R)-1-Methyl-4-(1-methylethenyl)cyclohexene; (R)-(+)-p-Mentha-1,8-diene; (+)-(4R)-Limonene; (+)-(R)-Limonene; (+)-Dipentene;(+)-Limonene;(+/-)-Limonene;(R)-(+)-Limonene;1-methyl-4-prop-1-en-2-ylcyclohexene;4-isopropenyl-1-methylcyclohexene;Cinene;Dipentene;Dipentene, technical grade;A-11638;A-25620;AGN-PC-014NSB;AY126431;DIV 03713;EN300-21627;L0046;QE-8187;T1295;T3241;DLIMONENE;d-limonene;dlimonene;d limonen; d-limonen; D LIMONEN; D LİMONEN; d lımonen; d-lımonen; D Lımonen; D limon; D-limonen D LIMON; limonen d

 

 

 

 

D-Limonene

D-Limonene is a clear colorless mobile liquid with a pleasant lemon-like odor. (NTP, 1992)

 


D-Limonene, (+)- is an oral dietary supplement containing a natural cyclic monoterpene and major component of the oil extracted from citrus peels with potential chemopreventive and antitumor activities. Although the mechanism of action has yet to be fully elucidated, D-Limonene and its metabolites perillic acid, dihydroperillic acid, uroterpenol and limonene 1,2-diol may inhibit tumor growth through inhibition of p21-dependent signaling and may induce apoptosis via the induction of the transforming growth factor beta-signaling pathway. In addition, they inhibit post-translational modification of signal transduction proteins, resulting in G1 cell cycle arrest as well as differential expression of cell cycle- and apoptosis-related genes.

 

NCI Thesaurus (NCIt)

D-Limonene

 

Not to be confused with Lemonene.
D-Limonene
Skeletal structure of the (R)-isomer
Ball-and-stick model of the (R)-isomer
rotating 3d D-Limonene molecule
D-Limonene extracted from orange peels.
Names
Preferred IUPAC name
1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
Other names
1-Methyl-4-(1-methylethenyl)cyclohexene
4-Isopropenyl-1-methylcyclohexene
p-Menth-1,8-diene
Racemic: DL-D-Limonene; Dipentene
Identifiers
CAS Number
138-86-3 (R/S) ☒
5989-27-5 (R) ☒
5989-54-8 (S) ☒
3D model (JSmol)
Interactive image
ChEBI 
CHEBI:15384 ☑
ChEMBL 
ChEMBL449062 (R) ☒
ChemSpider 
20939 (R/S) ☑
388386 (S) ☑
389747 (R) ☑
ECHA InfoCard 100.028.848
KEGG 
D00194 ☑
PubChem CID
22311 (R/S)
439250 (S)
UNII 
9MC3I34447 (R/S) ☒
GFD7C86Q1W (R) ☒
47MAJ1Y2NE (S) ☒
CompTox Dashboard (EPA)
DTXSID2029612 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula
C10H16
Molar mass 136.238 g·mol-1
Appearance colorless to pale-yellow liquid
Odor Orange
Density 0.8411 g/cm3
Melting point -74.35 °C (-101.83 °F; 198.80 K)
Boiling point 176 °C (349 °F; 449 K)
Solubility in water
Insoluble
Solubility Miscible with benzene, chloroform, ether, CS2, and oils
soluble in CCl4
Chiral rotation ([α]D)
87-102°
Refractive index (nD)
1.4727
Thermochemistry
Std enthalpy of
combustion (ΔcH⦵298)
-6.128 MJ mol-1
Hazards
Main hazards Skin sensitizer / Contact dermatitis - After aspiration, pulmonary oedema, pneumonitis, and death[1]
GHS pictograms GHS02: FlammableGHS07: HarmfulGHS08: Health hazardGHS09: Environmental hazard
GHS Signal word Danger
GHS hazard statements
H226, H304, H315, H317, H400, H410
GHS precautionary statements
P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+330+331, P302+352, P303+361+353, P304+340, P312, P333+313, P362, P370+378, P391, P403+233, P235, P405, P501
NFPA 704 (fire diamond) 
NFPA 704 four-colored diamond
230
Flash point 50 °C (122 °F; 323 K)
Autoignition
temperature
237 °C (459 °F; 510 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒ verify (what is ☑☒ ?)
Infobox references
D-Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels.[1] The D-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing.[1][2] It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products.[1] The less common L-isomer is found in mint oils and has a piny, turpentine-like odor.[1] The compound is one of the main volatile monoterpenes found in the resin of conifers, particularly in the Pinaceae, and of orange oil.

 

D-Limonene takes its name from French limon ("lemon").[3] D-Limonene is a chiral molecule, and biological sources produce one enantiomer: the principal industrial source, citrus fruit, contains D-D-Limonene ((+)-D-Limonene), which is the (R)-enantiomer.[1] Racemic D-Limonene is known as dipentene.[4] D-D-Limonene is obtained commercially from citrus fruits through two primary methods: centrifugal separation or steam distillation.

 


Contents
1 Chemical reactions
1.1 Biosynthesis
2 In plants
3 Safety and research
4 Uses
5 See also
6 References
7 External links
Chemical reactions
D-Limonene is a relatively stable monoterpene and can be distilled without decomposition, although at elevated temperatures it cracks to form isoprene.[5] It oxidizes easily in moist air to produce carveol, carvone, and D-Limonene oxide.[1][6] With sulfur, it undergoes dehydrogenation to p-cymene.[7]

 

D-Limonene occurs commonly as the D- or (R)-enantiomer, but racemizes to dipentene at 300 °C. When warmed with mineral acid, D-Limonene isomerizes to the conjugated diene α-terpinene (which can also easily be converted to p-cymene). Evidence for this isomerization includes the formation of Diels-Alder adducts between α-terpinene adducts and maleic anhydride.

It is possible to effect reaction at one of the double bonds selectively. Anhydrous hydrogen chloride reacts preferentially at the disubstituted alkene, whereas epoxidation with mCPBA occurs at the trisubstituted alkene.

In another synthetic method Markovnikov addition of trifluoroacetic acid followed by hydrolysis of the acetate gives terpineol.

 

Biosynthesis
In nature, D-Limonene is formed from geranyl pyrophosphate, via cyclization of a neryl carbocation or its equivalent as shown.[8] The final step involves loss of a proton from the cation to form the alkene.

 

center[Biosynthesis of D-Limonene from geranyl pyrophosphate

The most widely practiced conversion of D-Limonene is to carvone. The three-step reaction begins with the regioselective addition of nitrosyl chloride across the trisubstituted double bond. This species is then converted to the oxime with a base, and the hydroxylamine is removed to give the ketone-containing carvone.[2]

 

In plants
D-Limonene is a major component of the aromatic scents and resins characteristic for numerous coniferous and broadleaved trees: red and silver maple (Acer rubrum, Acer saccharinum), cottonwoods (Populus angustifolia), aspens (Populus grandidentata, Populus tremuloides) sumac (Rhus glabra), spruce (Picea spp.), various pines (examples, Pinus echinata, Pinus ponderosa), Douglas fir (Pseudotsuga menziesii), larches (Larix spp.), true firs (Abies spp.), hemlocks (Tsuga spp.), cannabis (Cannabis sativa spp.),[9] cedars (Cedrus spp.), various Cupressaceae and juniper bush (Juniperus spp.).[1] It contributes to the characteristic odor of orange peel, orange juice and other citrus fruits.[1][10] To optimize recovery of valued components from citrus peel waste, d-limonene is typically removed.[11]

 

 

Safety and research
D-Limonene applied to skin may cause irritation from contact dermatitis, but otherwise appears to be safe for human uses.[12][13] D-Limonene is flammable as a liquid or vapor and it is toxic to aquatic life.[1]

 

 

Uses
D-Limonene is common as a dietary supplement and as a fragrance ingredient for cosmetics products.[1] As the main fragrance of citrus peels, D-limonene is used in food manufacturing and some medicines, such as a flavoring to mask the bitter taste of alkaloids, and as a fragrance in perfumery, aftershave lotions, bath products, and other personal care products.[1] D-Limonene is also used as a botanical insecticide.[1][14] D-Limonene is used in the organic herbicide "Avenger".[15] It is added to cleaning products, such as hand cleansers to give a lemon or orange fragrance (see orange oil) and for its ability to dissolve oils.[1] In contrast, L-limonene has a piny, turpentine-like odor.

 

D-Limonene is used as a solvent for cleaning purposes, such as adhesive remover, or the removal of oil from machine parts, as it is produced from a renewable source (citrus essential oil, as a byproduct of orange juice manufacture).[11] It is used as a paint stripper and is also useful as a fragrant alternative to turpentine. D-Limonene is also used as a solvent in some model airplane glues and as a constituent in some paints. Commercial air fresheners, with air propellants, containing D-Limonene are used by philatelists to remove self-adhesive postage stamps from envelope paper.[16]

D-Limonene is also used as a solvent for fused filament fabrication based 3D printing.[17] Printers can print the plastic of choice for the model, but erect supports and binders from HIPS, a polystyrene plastic that is easily soluble in D-Limonene. As it is combustible, D-Limonene has also been considered as a biofuel.[18]

In preparing tissues for histology or histopathology, D-D-Limonene is often used as a less toxic substitute for xylene when clearing dehydrated specimens. Clearing agents are liquids miscible with alcohols (such as ethanol or isopropanol) and with melted paraffin wax, in which specimens are embedded to facilitate cutting of thin sections for microscopy.[19][20][21]

 

See also
Monoterpenes
Resin
Essential oil

 

D-Limonene is the oil extracted from the peels of oranges and other citrus fruits (1).

People have been extracting essential oils like D-Limonene from citrus fruits for centuries. Today, D-Limonene is often used as a natural treatment for a variety of health issues and is a popular ingredient in household items.

However, not all of D-Limonene's benefits and uses are supported by science.

This article examines D-Limonene's uses, potential benefits, side effects, and dosage.

 

What is D-Limonene?
D-Limonene is a chemical found in the rind of citrus fruits, such as lemons, limes, and oranges. It is especially concentrated in orange peels, comprising around 97% of this rind's essential oils (2Trusted Source).

 

It's often referred to as d-Limonene, which is its main chemical form.

D-Limonene belongs to a group of compounds known as terpenes, whose strong aromas protect plants by deterring predators (3Trusted Source).

D-Limonene is one of the most common terpenes found in nature and may offer several health benefits. It has been shown to possess anti-inflammatory, antioxidant, anti-stress, and possibly disease-preventing properties.

 

SUMMARY
D-Limonene is an essential oil found in citrus fruit peels. It belongs to a class of compounds called terpenes.
Common uses of D-Limonene
D-Limonene is a popular additive in foods, cosmetics, cleaning products, and natural insect repellants. For example, it's used in foods like sodas, desserts, and candies to provide a lemony flavor.

 

D-Limonene is extracted through hydrodistillation, a process in which fruit peels are soaked in water and heated until the volatile molecules are released via steam, condensed, and separated (4).

Due to its strong aroma, D-Limonene is utilized as a botanical insecticide. It's an active ingredient in multiple pesticide products, such as eco-friendly insect repellents (5).

Other household products containing this compound include soaps, shampoos, lotions, perfumes, laundry detergents, and air fresheners.

Additionally, D-Limonene is available in concentrated supplements in capsule and liquid form. These are often marketed for their supposed health benefits.

This citrus compound is also used as an aromatic oil for its calming and therapeutic properties.

 

SUMMARY
D-Limonene is used in a range of products, including food, cosmetics, and eco-friendly pesticides. It can also be found in supplement form, as it may boost health and fight certain diseases.
Linked to several health benefits
D-Limonene has been studied for its potential anti-inflammatory, antioxidant, anticancer, and heart-disease-fighting properties.

 

However, most research has been conducted in test tubes or on animals, making it difficult to fully understand the role of D-Limonene in human health and disease prevention.

 

Anti-inflammatory and antioxidant benefits
D-Limonene has been shown to reduce inflammation in some studies (6Trusted Source, 7Trusted Source).

 

While short-term inflammation is your body's natural response to stress and is beneficial, chronic inflammation can harm your body and is a major cause of illness. It's important to prevent or reduce this type of inflammation as much as possible (8Trusted Source).

D-Limonene has been shown to reduce inflammatory markers that relate to osteoarthritis, a condition characterized by chronic inflammation.

A test-tube study in human cartilage cells noted that D-Limonene reduced nitric oxide production. Nitric oxide is a signaling molecule that plays a key role in inflammatory pathways (9Trusted Source).

In a study in rats with ulcerative colitis - another disease characterized by inflammation - treatment with D-Limonene significantly decreased inflammation and colon damage, as well as common inflammatory markers (10Trusted Source).

D-Limonene has demonstrated antioxidant effects as well. Antioxidants help reduce cell damage caused by unstable molecules called free radicals.

Free radical accumulation can lead to oxidative stress, which may trigger inflammation and disease (11Trusted Source).

One test-tube study revealed that D-Limonene may inhibit free radicals in leukemia cells, suggesting a decrease in inflammation and cellular damage that would normally contribute to disease (12Trusted Source).

Although promising, these effects need to be confirmed by human studies.

 

May have anticancer effects
D-Limonene may have anticancer effects.

 

In a population study, those who consumed citrus fruit peel, the major source of dietary D-Limonene, had a reduced risk of developing skin cancer compared to those who only consumed citrus fruits or their juices (13Trusted Source).

Another study in 43 women recently diagnosed with breast cancer experienced a significant 22% reduction in breast tumor cell expression after taking 2 grams of D-Limonene daily for 2-6 weeks (14Trusted Source).

Additionally, research in rodents found that supplementing with D-Limonene inhibited the growth of skin tumors by preventing inflammation and oxidative stress (15Trusted Source).

Other rodent studies indicate that D-Limonene may fight other types of cancer, including breast cancer (16Trusted Source).

What's more, when given to rats alongside the anticancer drug doxorubicin, D-Limonene helped prevent several common side effects of the medication, including oxidative damage, inflammation, and kidney damage (17Trusted Source).

Although these results are promising, more human studies are needed.

 

May boost heart health
Heart disease remains the leading cause of death in the United States, accounting for nearly one in four deaths (18Trusted Source).

 

D-Limonene may lower your risk of heart disease by reducing certain risk factors, such as elevated cholesterol, blood sugar, and triglyceride levels.

In one study, mice given 0.27 grams of D-Limonene per pound of body weight (0.6 grams/kg) showed reduced triglycerides, LDL (bad) cholesterol, fasting blood sugar, and fat accumulation in the liver, compared to a control group (19Trusted Source).

In another study, stroke-prone rats given 0.04 grams of D-Limonene per pound of body weight (20 mg/kg) exhibited significant reductions in blood pressure compared to rats of similar health status that did not receive the supplement (20Trusted Source).

Keep in mind that human studies are needed before strong conclusions can be drawn.

 

Other benefits
Aside from the benefits listed above, D-Limonene may:

 

 

Reduce appetite. The scent of D-Limonene has been shown to significantly reduce appetite in blowflies. However, this effect has not been studied in humans (21Trusted Source).
Decrease stress and anxiety. Rodent studies suggest that D-Limonene could be used in aromatherapy as an anti-stress and anti-anxiety agent (22Trusted Source).
Support healthy digestion. D-Limonene may protect against stomach ulcers. In a study in rats, citrus aurantium oil, which is 97% D-Limonene, protected nearly all of the rodents against ulcers caused by medication use (23Trusted Source).
SUMMARY
D-Limonene may offer antioxidant, anti-inflammatory, anticancer, and anti-heart-disease benefits, among others. However, more research in humans is needed.
Safety and side effects
D-Limonene is considered safe for humans with little risk of side effects. The Food and Drug Administration (FDA) recognizes D-Limonene as a safe food additive and flavoring (5).

 

However, when applied directly to the skin, D-Limonene may cause irritation in some people, so caution should be used when handling its essential oil (24Trusted Source, 25).

D-Limonene is sometimes taken as a concentrated supplement. Because of the way your body breaks it down, it's likely safe consumed in this form. That said, human research on these supplements is lacking (26Trusted Source).

Notably, high-dose supplements may cause side effects in some people. What's more, insufficient evidence exists to determine whether D-Limonene supplements are acceptable for pregnant or breastfeeding women.

It's best to consult your healthcare practitioner before taking D-Limonene supplements, especially if you're taking medications, are pregnant or breastfeeding, or have a medical condition.

 

SUMMARY
Aside from possible skin irritation associated with direct application, D-Limonene is likely safe for most people to use and consume in moderation.

 

 

Potentially effective dosages
Because few D-Limonene studies exist in humans, it's difficult to provide a dosage recommendation.

 

Nonetheless, dosages of up to 2 grams daily have been safely used in studies (9Trusted Source, 14Trusted Source).

Capsule supplements that can be purchased online contain dosages of 250-1,000 mg. D-Limonene is also available in liquid form with typical dosages of 0.05 ml per serving.

However, supplements aren't always necessary. You can easily obtain this compound by eating citrus fruits and peels.

For example, fresh orange, lime, or lemon zest can be used to add D-Limonene to baked goods, drinks, and other items. What's more, pulpy citrus juices, such as lemon or orange juice, boast D-Limonene, too (27Trusted Source).

 

SUMMARY
While dosage recommendations don't exist for D-Limonene, 2 grams daily has been safely used in studies. In addition to supplements, you can obtain D-Limonene from citrus fruits and zest.
The bottom line
D-Limonene is a compound extracted from the peels of citrus fruits.

 

Studies suggest that D-Limonene may have anti-inflammatory, antioxidant, and anticancer effects. However, more research in humans is needed to confirm these benefits.

Try adding lemon, lime, or orange zest to your favorite dishes to boost your D-Limonene intake.

 

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D-D-Limonene is a compound sourced from the peel of citrus fruits, including include oranges, mandarins, limes, and grapefruit. It takes its name from the lemon and is often used as a flavoring agent in foods. D-D-Limonene differs from a less common type of D-Limonene known as L-D-Limonene, which is found in mint oil.

 


Sold as a dietary supplement, D-D-Limonene is said to offer a variety of health benefits, in part because of its ability to dissolve fats, including cholesterol. Proponents believe that D-D-Limonene can not only aid in weight loss but treat or prevent certain diseases, including cancer.

 

 

Health Benefits
Alternative practitioners have long touted the benefits of D-D-Limonene, claiming that it not only burns fat but reduces inflammation and kills disease-causing germs. Many of these beliefs are culled from its use in industry, where D-D-Limonene is commonly used to make hand sanitizers, perfumes, botanical pesticides, and chemical solvents.

 

Among some of the conditions that D-D-Limonene is believed to prevent or treat are:

 


Bronchitis
Cancer
Diabetes
Gallstones
Gastroesophageal reflux disease (GERD)
Heartburn
High cholesterol
Inflammatory bowel disease (IBD)
Metabolic syndrome
Obesity
Peptic ulcers

 

Citrus essential oils rich in D-D-Limonene are also used in aromatherapy to relieve stress.

To date, there is little solid evidence that D-D-Limonene can treat any medical condition. With that said, a number of preliminary studies have hinted at benefits that may warrant further investigation.

 


Weight Loss
There is some evidence that D-Limonene can promote weight loss by lowering blood sugar and lipids associated with metabolic syndrome. A 2013 study in the European Journal of Pharmacology reported that obese mice fed a high-diet diet supplemented with D-Limonene experienced decreases in blood glucose, total cholesterol, and "bad" LDL cholesterol as well as increases in "good" HDL cholesterol.

 

 


These findings suggest that D-limonene may be useful in preventing or treating metabolic syndrome, although it is unclear what dose would be needed to achieve such benefit in humans. Further research is needed.

 

 


Peptic Ulcers
D-limonene may help reduce the risk of peptic ulcers and other inflammatory gastrointestinal diseases, suggests a 2009 study published in the Chemico-Biological Interactions. According to the researchers, high concentrations of D-limonene in the essential oil of bitter orange (C. aurantium) served to protect the lining of the stomach of lab rats fed high-doses of alcohol and nonsteroidal anti-inflammatory drugs (NSAIDs).

 

Contrary to popular belief, it did so not by suppressing stomach acid but by increasing the production of gastric mucus.

Despite the positive findings, it is unclear if D-limonene did so on its own or if some other component in the essential oil contributed. Further research is needed.

 

Treating Peptic Ulcers With Diet
Cancer
Alternative practitioners have long touted the anticancer properties of D-limonene. The effect of is attributed to a substance known as perillic acid, which is released into the bloodstream when D-limonene is broken down by the body.

 

A number of test-tube studies have reported that D-D-Limonene applied to cancer cells can trigger apoptosis (programmed cell death). This is considered significant given that apoptosis-a naturally occurring event that allows old cells to be replaced by new cells-does not occur with cancer cells. This effect was seen in recent studies involving colon cancer,1 skin cancer,2 and other common malignancies.

It remains unclear whether taking D-limonene by mouth might render the same benefit. A 2013 study in Cancer Prevention Research aimed to evaluate this effect by providing 43 women with breast cancer with 2 grams of D-limonene daily for two to six weeks.

At the end of the study period, a biopsy of breast tissue showed high concentrations of D-limonene but little of the perillic acid needed to arrest cancer growth. Further research is needed to determine whether higher doses or longer treatment may help improve these results.

 

Can Green Tea Prevent Colon Cancer?
Possible Side Effects
Widely used as a food flavoring, D-limonene is generally considered safe and has been used for up to a year in clinical research without incidence. Common side effects include stomach upset and reflux.

 

At excessively high doses, D-limonene has been known to hematuria (blood in urine).3

D-limonene may cause irritation if applied to the skin. This includes citrus essential oils that are characteristically high in D-limonene. To reduce irritation, always mix essential oils with a carrier oil (such as avocado oil or sweet almond oil) if you intend to use it for massage purposes.

The safety of D-limonene has not been established in children, pregnant women, or nursing mother. As a precaution, always speak with your doctor before using D-limonene or any other supplement if you are pregnant or breastfeeding. As the benefits of D-limonene in children is unknown, it is best to play it safe and avoid the supplement altogether.

 

Interactions
D-limonene is broken down by many of the same liver enzymes-called cytochrome P450 (CYP450)-that other drugs use for metabolization. Because of this, D-limonene may increase or decrease the concentration of certain drugs as they compete for the same enzyme.

 

Possible drug-drug interactions include:

 

Anticoagulants like Coumadin (warfarin)
Anticonvulsants like Tegretol (carbamazepine)
Antifungal drugs like Nizoral (ketoconazole)
Anti-hypertensive medications like Cozaar (losartan)
Antipsychotic drugs like Orap (pimozide)
Atypical antidepressants like nefazodone
Benzodiazepine tranquilizers like Halcion (triazolam)
H2 blockers like Tagamet (cimetidine)
Macrolide antibiotics like clarithromycin and telithromycin
Nonsteroid anti-inflammatory drugs (NSAIDs) like Advil (ibuprofen) and Voltaren (diclofenac)
Proton pump inhibitors like Prilosec (omeprazole)

 

Many of these interactions can be mitigated by separating the doses by two to four hours. Others may require a dose adjustment or substitution.

To avoid interactions, always advise your doctor about any medications you are taking, whether they are prescription, over-the-counter, nutritional, herbal, or recreational.

 

Dosage and Preparations
D-limonene supplements are most often sold in soft gel capsules and are easily sourced online or in stores specializing in dietary supplements.

 

While there are no guidelines for the appropriate use of D-limonene, most manufacturers recommend a dose of between 500 milligrams (mg) and 1,000 mg per day, taken with or without food.

As a rule of thumb, never exceed the dose on the product label. There is no evidence that higher doses confer to improved health benefits.

Most D-limonene soft gels can be stored safely at room temperature. You can also keep them in the refrigerator if there is a risk of heat exposure. Never use a supplement past its expiration date, and dispose of any soft gels that are either leaking, discolored, or misshapen.

 

What to Look For
Because dietary supplements are not strictly regulated in the United States, it can be difficult to tell which brands are good and which are not.

 

One way to do so is to choose brands that have been tested by an independent certifying body like the U.S. Pharmacopeia (USP), NSF International, or ConsumerLab.

Certification doesn't mean that the supplement is either safe or effective; it simply indicates that it contains the ingredients listed on the product label and in the correct amounts.

Always check the product label for ingredients you may be sensitive to, including preservatives and gluten. If you are strictly vegetarian or vegan, opt for soft gels made with vegetable-based gelatin rather than animal-based gelatins made from beef or pork cartilage.

 


EC Number: 227-813-5

 

 

IUPAC Name
(4R)-1-methyl-4-prop-1-en-2-ylcyclohexene

 

 

Molecular Formula
C10H16

 

 

Physical Description
PHYSICAL DESCRIPTION: Clear colorless mobile liquid with a pleasant lemon-like odor.

 

 

Odor
Citrus odor

 

 

Taste
FRESH, CITRUS TASTE

 

Limonene, (+)- is an oral dietary supplement containing a natural cyclic monoterpene and major component of the oil extracted from citrus peels with potential chemopreventive and antitumor activities. Although the mechanism of action has yet to be fully elucidated, limonene and its metabolites perillic acid, dihydroperillic acid, uroterpenol and limonene 1,2-diol may inhibit tumor growth through inhibition of p21-dependent signaling and may induce apoptosis via the induction of the transforming growth factor beta-signaling pathway. In addition, they inhibit post-translational modification of signal transduction proteins, resulting in G1 cell cycle arrest as well as differential expression of cell cycle- and apoptosis-related genes.

 

Limonene is a monoterpene with a clear colourless liquid at room temperature, a naturally occurring chemical which is the major component in oil of oranges. Limonene is widely used as a flavor and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182. 60 in the Code of Federal Regulations, U. S. A. ). Limonene is a botanical (plant-derived) solvent of low toxicity. Mild skin irritation may occur from exposure to limonene and oxidation products of limonene may produce dermal sensitization, and may have irritative and bronchoconstrictive airway effects; however, data are scant and more studies are required. Limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Furthermore, chronic exposure to limonene causes a significant incidence of renal tubular tumors exclusively in male rats. Limonene is one of the active components of dietary phytochemicals that appears to be protective against cancer. (PMID: 16563357, 15499193, 15325315, 2024047).

 


PHYSICAL DESCRIPTION: Clear colorless mobile liquid with a pleasant lemon-like odor

 

D-Limonene is a molecule that is found in high levels in lemons (where it derives its name) but also most citrus foods. It holds promise as an anti-cancer agent, and for some reason is marketed as a fat burner despite minimal evidence of fat burning effects. Can be consumed via pulpy lemon juice.

The monoterpene d-limonene is a naturally occurring chemical which is the major component in oil of orange. Currently, d-limonene is widely used as a flavor and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration. Recently, however, d-limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Furthermore, chronic exposure to d-limonene causes a significant incidence of renal tubular tumors exclusively in male rats. Although d-limonene is not carcinogenic in female rats or male and female mice given much higher dosages, the male rat-specific nephrocarcinogenicity of d-limonene may raise some concern regarding the safety of d-limonene for human consumption. A considerable body of scientific data has indicated that the renal toxicity of d-limonene results from the accumulation of a protein, alpha 2u-globulin, in male rat kidney proximal tubule lysosomes. This protein is synthesized exclusively by adult male rats. Other species, including humans, synthesize proteins that share significant homology with alpha 2u-globulin. However, none of these proteins, including the mouse equivalent of alpha 2u-globulin, can produce this toxicity, indicating a unique specificity for alpha 2u-globulin. With chronic exposure to d-limonene, the hyaline droplet nephropathy progresses and the kidney shows tubular cell necrosis, granular cast formation at the corticomedullary junction, and compensatory cell proliferation. Both d-limonene and cis-d-limonene-1,2-oxide (the major metabolite involved in this toxicity) are negative in vitro mutagenicity screens. Therefore, the toxicity-related renal cell proliferation is believed to be integrally involved in the carcinogenicity of d-limonene as persistent elevations in renal cell proliferation may increase fixation of spontaneously altered DNA or serve to promote spontaneously initiated cells. The scientific data base demonstrates that the tumorigenic activity of d-limonene in male rats is not relevant to humans. The three major lines of evidence supporting the human safety of d-limonene are the male rat specificity of the nephrotoxicity and carcinogenicity; the pivotal role that alpha 2u-globulin plays in the toxicity, as evidenced by the complete lack of toxicity in other species despite the presence of structurally similar proteins; and the lack of genotoxicity of both d-limonene and d-limonene-1,2-oxide, supporting the concept of a nongenotoxic mechanism, namely, sustained renal cell proliferation.

This compound belongs to the class of chemical entities known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

 

 

 

D-LİMONENE (D-LİMONEN) 

Limon Kabuğunu; Soğuk içeceklerde yaygınca kullanan akdeniz mutfağını araştıran bilimsel çalışmalar tesadüfen kanser ve kronik hastalıkların neden az görüldüğünün sebebini bulmuşlardır.

 

Sıvı D-Limonen; Anavatanı Hindistan ve uzakdoğu olan özel kokulu bir yağ içeren Limon Kabuğu bitkisel bir ilaçtır. Antioksidan maddeler yüksek miktarlarda mevcuttur.

D-Limonen Sıvı etken maddesi diğer turunçgillerin kabuğundada bulunmaktadır. Kanserin yanı sıra yüksek tansiyonda, kötü kolestrolün düşmesinde, iyi kolestrolün, artmasında, kalp damar tıkanıklarında faydalıdır.

D-limonene genelde kolonya, deterjan gibi ürünlerin üretiminde kullanılır. D'limonen %100 natüreldir.

TANIM: D'Limonen (D'Limonene)

EŞ ANLAMI: Citrus Terpene

KİMYASAL İSMİ: 1,8(9)-p-Menthadiene; 1-Methyl-4-isopropenyl-1-cyclohexene

KİMYASAL FORMULÜ: C10H16 (FW=136.2)

ÖZELLİKLERİ: Kokusu hissedilebilen ve su ile karışmayan sıvı maddedir. Yanıcı uçucu maddedir. Saf olarak deri ve gözde tahrişe neden olur. 23-61 derece arasında alev alır.

FİZYOLİJİK ÖZELLİKLER: Görünüş: renksiz sıvı, Koku: trunça has kokuda tatlı, Yoğunluk: 0.834-0.854 g/cm3 20Cde, Kırılma indexi: 1.470-1.480 20Cde, Parlama derecesi 50C

SAKLAMA KOŞULLARI: Kapalı konteynırda, ışıktan sıcaklıktan uzak olmalıdır. Raf ömrü 12 aydır.

ÖZEL KODLAR: Yanıcı, ADR'ye göre sınıfı 3.31c,UN 2319, IMO 3.3, CAS 5989-54-8, FEMA 2633, CAS 8028-48-6, FEMA 2825,

KULLANIM ALANI: Kozmetik, Kolonya , Deterjan üretiminde limon koku vermesi amacı ile kullanılır. Özellikle sıvı ve jel bulaşık deterjanlarında kullanılır. İstenirse kendi formulunüzle karışım yapılıp maliyet düşürülebilir. D'limonene limon ve lime nin distilasyonu ile elde edilir. %100 natürel bir madde olduğundan limon kokulu ürünlerin üretilmesinde d'limonen kullanılması tavsiye edilir. Ayrıca, temizlik gücünü arttırıcı özelliği vardır. Yağlı bir bölgeye dökerseniz yağı çözer.

D-Limonene (Citrus Terpene)

Citrus Terpen bir diğer adıyla D Limonene yağlar, toplanan narenciyelerin kabuğundan elde edilmektedir. Yoğunlukla parfüm ve esans endüstrisinde kullanılır.

 

Turunçgil kabuğundaki mucize: D- Limonene
Giriş Tarihi: 6.10.2013
ABONE OL 
Turunçgillerin kabuklarından elde edilen D-limonene; kanser tedavisinde kullanılıyor. D-limonene; tümörlerin büyümesini engellemektedir. Hayvanlar üzerinde yapılan deneyler bu maddenin; pankreas, meme, mide, kolon, deri ve karaciğer kanserlerinde etkili olduğunu gösteriyor. D-limonene, oluşmuş tümörlerin büyümesini de engelliyor.

 

 

YAN ETKİSİ VAR
D-limonene'nin yan etkileri arasında mide bulantısı, kusma ve ishal görülmektedir. Hayvanlar üzerinde yapılan deneyler; D-limonene'nin kanser tedavisinde etkili olduğunu göstermiştir ama insanlar üzerindeki etkisi kanıtlanmamıştır. Yapılan bazı araştırmalar ise; mandalina kabuğunun, beyin tümörlerinde etkili olduğunu gösterdi.

 

 

D-Limonene Nedir, Ne İşe Yarar?
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1.042 kez görüntülendi.

 

D-Limonene, portakal ve diğer narenciye kabuklarından çıkarılan yağdır. İnsanlar yüzyıllardır narenciye meyvelerinden bunun gibi esansiyel yağları alıyorlar. Günümüzde bu yağ, çeşitli sağlık sorunları için doğal bir tedavi olarak kullanılmaktadır.

 

 

İçindekiler
1) D-Limonene nedir?
2) D-Limonene Kullanım Alanları
3) D-Limonene nasıl elde edilir?
4) D-Limonene Faydaları
5) D-Limonene Zararları
D-Limonene nedir?
Limon, misket limonu ve portakal gibi turunçgillerin kabuğunda bulunan bir kimyasaldır. Özellikle portakal kabuklarında yoğunlaşmıştır, portakal kabuğunun yaklaşık % 97'si esansiyel yağlar içerir. Ana kimyasal formu ise d-D-Limonen olarak adlandırılır.

 

Bu bileşiğin güçlü aroması, bitkileri hayvanlardan koruyan, terpen olarak bilinen bir grup bileşiğe aittir.

D-Limonene, doğada en yaygın bulunan terpenlerden biridir ve çeşitli sağlık yararları vardır. Anti-inflamatuar, antioksidan, anti-stres ve hastalık önleyici özelliklere sahip olduğu belirtilmektedir.

 

d D-Limonene nedir

 

 

D-Limonene Kullanım Alanları
Bu esansiyel yağ; gıdalar, kozmetikler, temizlik ürünleri ve doğal böcek kovucular için bir katkı maddesidir. Gazlı içecekler, tatlılar ve şekerler gibi yiyeceklere limonlu lezzet vermek için de kullanılır.

 

 

 

D-Limonene nasıl elde edilir?
Meyve kabukları suya batırılarak, uçucu moleküller buhar yoluyla yoğunlaşıp salıverilene ve ayrılana kadar ısıtılan bir işlem olan "hidrodistilizasyon" yoluyla çıkarılır.

 

Güçlü aroması nedeniyle D-Limonene, böcek ilacı olarak kullanılır. Çevre dostu böcek kovucularda aktif kullanılan bir maddedir.

Bu bileşiği içeren diğer ev ürünleri sabunlar, şampuanlar, losyonlar, parfümler, çamaşır deterjanları ve oda spreyleridir. Bu narenciye bileşiği aynı zamanda sakinleştirici ve terapötik özellikleri için aromatik bir yağ olarak da kullanılır.

 


D-Limonene Faydaları

Anti-inflamatuar ve antioksidan yararları

 

Bazı çalışmalarda bu narenciye bileşiğinin, iltihabı azalttığı gösterilmiştir. D-Limonenin, kronik enflamasyonla karakterize bir durum olan osteoartritle ilgili enflamatuar markerleri azalttığı da belirtilmiştir.

Antioksidan etkileri olduğu da tespit edilmiştir. Antioksidanlar serbest radikal adı verilen dengesiz moleküllerin neden olduğu hücre hasarını azaltmaya yardımcı olur.

Bir test tüpü çalışması, D-Limonenin lösemi hücrelerinde serbest radikalleri inhibe edebileceğini ortaya koydu.

İlginizi Çekebilir Elma Sirkesinin Faydaları ve Zararları Nelerdir?

Antikanser etkileri

D-Limonen antikanser etkilere sahip olabilir. Yakın zamanda meme kanseri tanısı alan 43 kadında yapılan bir çalışmada, 2-6 hafta boyunca günde 2 gram D-Limonen aldıktan sonra, meme tümörü hücre ekspresyonunda % 22'lik bir azalma görülmüştür.

Ek olarak, kemirgenlerde yapılan araştırmalar, D-Limonen desteğinin, iltihabı ve oksidatif stresi önleyerek, cilt tümörlerinin büyümesini engellediğini bulmuştur.

Diğer kemirgen çalışmaları, D-Limonenin meme kanseri dahil diğer kanser türleriyle savaşabileceğini göstermektedir.

 


Kalp sağlığına faydaları

 

Bu narenciye bileşiği, yüksek kolesterol, kan şekeri ve trigliserit seviyeleri gibi belirli risk faktörlerini azaltarak kalp hastalığı riskini düşürür.

Bir çalışmada, vücut ağırlığının kilogramı başına (0.6 gram / kg) D-Limonene verilen fareler, kontrol grubuna kıyasla karaciğerde trigliserit, LDL (kötü) kolesterol, açlık kan şekeri ve yağ birikimini düşürdü.

 

Yukarıda listelenen faydaların yanı sıra bu narenciye bileşiğinin şu etkileri de vardır:

İştahı azaltır

D-Limonene kokusu, böceklerde iştahı önemli ölçüde azaltmıştır. Ancak bu etki insanlarda çalışılmamıştır.

Stres ve kaygıyı azaltır

Kemirgen çalışmaları, bu narenciye bileşiğinin aromaterapide bir anti-stres ve anti-anksiyete ajanı olarak kullanılabileceğini göstermektedir.

 


Sindirim sağlığını destekler

 

D-Limonene, mide ülserine karşı korur. Sıçanlarda yapılan bir çalışmada, % 97 bu bileşiği içeren "sitrus aurantium yağı", ilaç kullanımının neden olduğu ülsere karşı neredeyse tüm kemirgenleri korumuştur.

 

D-Limonene Zararları
Yan etki riski az olan bir bileşiktir ve insanlar için güvenli olarak kabul edilir. Gıda ve İlaç İdaresi (FDA) bunu güvenli bir gıda katkı maddesi ve tatlandırıcı olarak tanır.

 

Ancak, doğrudan cilde uygulandığında bazı insanlarda tahrişe neden olabilir, bu nedenle esansiyel yağını kullanırken dikkatli olunmalıdır.

D-Limonene bazen konsantre destek olarak alınır. Vücudun onu parçalama biçimi nedeniyle, bu formda tüketilmesi muhtemelen güvenlidir.

Ancak yine de dikkatli olunmalıdır çünkü bu konu üzerine insan araştırması eksiktir. Özellikle, yüksek dozlar bazı kişilerde yan etkilere neden olabilir.

Dahası, D-Limonen takviyelerinin hamile veya emziren kadınlar için etkinliğini belirlemek için yeterli kanıt yoktur. Bunu kullanmadan önce doktora danışmak gerekir.

 

 

İlginizi Çekebilir En Sağlıklı D Vitamini Miktarı Hangisi?
Sonuç olarak;

 

D-Limonene, turunçgil meyvelerin kabuğundan elde edilen bir bileşiktir. Çalışmalar, anti-inflamatuar, antioksidan ve antikanser etkileri olabileceğini göstermektedir.

 

TARTIŞMA ve SONUÇ
Doğadaki en önemli kural madde akış döngüsünün sağlanmasıdır. Organik bir atık olan
portakal kabuğunun tekrar değerlendirilerek geri dönüştürülmesinin sağlanması hem
ekonomik hem de doğal madde döngüsü için oldukça önemlidir. Uçucu yağlar sahip
oldukları kimyasal bileşenlerden dolayı patojenik mikroorganizmalar üzerinde inhibe edici
etkiye sahiptirler. Çalışma sonuçlarına göre portakal kabuğundan elde edilen uçucu yağ
%73' lük oranla D-D-Limonen, %7 myrcene, %3,5 valencene, %3 alpha-Terpineol, %2,5 αPinene, %2 6-octen-1-ol, 3,7-Dimethyl (-R), %1,5 alpha-Terpinene ve %1 gammaTerpinene içerdiği tespit edilmiştir. Portakal kabuğunda bulunan D-Limonen bileşeninin
antibakteriyel ve antiseptik aktivitelere sahip olduğu yapılan çalışmalarla belirlenmiştir
(Magwa vd., 2006; Geraci vd., 2017). Turunçgillerden elde edilen yağlarda, fazla
miktarda monoterpen hidrokarbon (%70-95) içermekte ve D-D-Limonen, bildirilen tüm tatlı
portakal yağlarında baskın olarak bulunmaktadır (Geraci vd., 2017). Portakal kabuğunda
yapılan kimyasal içerik çalışmaları incelendiğinde çalışmamızla uyumlu olarak en önemli
bileşenin D-Limonen olduğu rapor edilmiştir (Dugo ve Mondella, 2011; Debbarma vd., 2013;
Geraci vd., 2017). Yapılan başka bir çalışma incelendiğinde, portakal uçucu yağının
başlıca ana bileşen olarak % 77.37 oranında D-Limonen içerdiği belirlenmiştir.

 

D-Limonen : limon kabuklarının basit damıtma yöntemiyle damıtılması sonucu elde edilen organik bileşiğin ekstraktesiyle oluşan kokusu güzel esans.

D-Limonen , birçok bitki türünün esansiyel yağlarında bulunur ve portakalın ana aroma bileşenidir

 

-akciğerleri korur.
-karaciğeri temizler.
-kolesterolü düşürür.
-kolon kanserini önler.

 

D-Limonen ,bitkilerde yaygın olarak bulunan hidrokarbondur..

D-Limonen ,özellikle turunçgillerin kabuğundan elde edilen uçucu özellikte bir çözücüdür..

D-Limonen

 

Limon ile karıştırılmamalıdır.
D-Limonen
(R) -izomerinin iskelet yapısı
(R) izomerinin top ve çubuk modeli
dönen 3d D-Limonen molekülü
Portakal kabuklarından elde edilen D-Limonen.
İsimler
Tercih edilen IUPAC adı
1-metil-4- (prop-1-en-2-il) sikloheks-1-en
Diğer isimler
1-metil-4- (1-metiletenil) sikloheksen
4-İzopropenil-1-metilsikloheksen
p-ment-1,8-dien
Rasemik: DL-D-Limonen; dipenten
Tanımlayıcılar
CAS numarası
138-86-3 (R / S) ☒
5989-27-5 (R) ☒
5989-54-8 (S) ☒
3D model (JSmol)
Etkileşimli görüntü
Chebi
CHEBI: 15384 ☑
ChEMBL
ChEMBL449062 (R) ☒
ChemSpider

 

 

Özellikleri
Kimyasal formül
C10H16
Molar kütle 136.238 g · mol - 1
Görünüş renksiz ila soluk sarı sıvı
Koku Portakal
Yoğunluk 0.8411 g / cm3
Erime noktası -74.35 ° C (-101.83 ° F; 198.80 K)
Kaynama noktası 176 ° C (349 ° F; 449 K)
sudaki çözünürlük
çözünmez
Çözünürlük Benzen, kloroform, eter, CS2 ve yağlarla karışabilir
CCl4 içinde çözünür
Kiral rotasyon ([α] D)
87-102 °
Kırılma indisi (nD)
1,4727
Termokimya
Std entalpisi
yanma (ΔcH⦵298)
.16.128 MJ mol - 1

 

 

Parlama noktası 50 ° C (122 ° F; 323 K)
otomatik ateşleme
sıcaklık
237 ° C (459 ° F; 510 K)
Aksi belirtilmedikçe, standart halindeki malzemeler için veriler verilir (25 ° C [77 ° F], 100 kPa'da).
☒ doğrula (☑☒ nedir?)
Bilgi kutusu referansları
D-Limonen, siklik monoterpen olarak sınıflandırılan renksiz bir sıvı alifatik hidrokarbondur ve turunçgiller kabuklarının yağındaki ana bileşendir. [1] Doğada daha yaygın olarak portakal kokusu olarak ortaya çıkan D-izomeri, gıda üretiminde lezzet verici bir maddedir. [1] [2] Ayrıca kimyasal sentezde karvonun öncüsü ve temizlik ürünlerinde yenilenebilir bazlı bir çözücü olarak kullanılır. [1] Daha az yaygın olan L-izomeri nane yağlarında bulunur ve keskin, terebentin benzeri bir kokuya sahiptir. [1] Bileşik, iğne yapraklıların reçinesinde, özellikle Pinaceae'de ve portakal yağında bulunan ana uçucu monoterpenlerden biridir.

 

D-Limonene adını Fransız limonundan ("limon") alır. [3] D-Limonen kiral bir moleküldür ve biyolojik kaynaklar bir enantiyomer üretir: başlıca endüstriyel kaynak, turunçgiller, (R) -enantiyomer olan D-D-Limonen ((+) - D-Limonen) içerir. [1] Rasemik D-Limonen, dipenten olarak bilinir. [4] D-D-Limonen ticari olarak turunçgillerden iki ana yöntemle elde edilir: santrifüjlü ayırma veya buharla damıtma.

 

Kimyasal reaksiyonlar
D-Limonen nispeten stabil bir monoterpendir ve yüksek sıcaklıklarda izopren oluşturmak için çatlamasına rağmen, ayrışma olmadan damıtılabilir. [5] Karveol, karvon ve D-Limonen oksit üretmek için nemli havada kolayca oksitlenir. [1] [6] Sülfür ile p-serine dehidrojenasyona uğrar. [7]

 

D-Limonen yaygın olarak D- veya (R) -enantiyomer olarak bulunur, ancak 300 ° C'de dipentene racemizes. Mineral asit ile ısıtıldığında, D-Limonen konjüge dien a-terpinene (ayrıca kolayca p-serine dönüştürülebilen) izomerleşir. Bu izomerizasyonun kanıtı, a-terpinen eklentileri ve maleik anhidrit arasında Diels-Alder eklentilerinin oluşumunu içerir.

Çift bağlardan birinde reaksiyonu seçici olarak gerçekleştirmek mümkündür. Susuz hidrojen klorür tercihen ikame edilmemiş alkende reaksiyona girerken, mCPBA ile epoksidasyon, trisübstitüe edilmiş alkende gerçekleşir.

Başka bir sentetik yöntemde Markovnikov, trifloroasetik asit ilave edildikten sonra asetatın hidrolizi, terpineol verir.

 

biosentezi
Doğada, D-Limonen, gösterildiği gibi bir neril karbokasyonu veya eşdeğerinin siklizasyonu yoluyla sardunil pirofosfattan oluşur. [8] Son adım, alken oluşturmak için katyondan bir proton kaybını içerir.

 

merkezi [Sardunil pirofosfattan D-Limonen biyosentezi

D-Limonene'nin en yaygın olarak uygulanan dönüşümü karvandır. Üç aşamalı reaksiyon, üç kez ikame edilmiş çift bağ boyunca bölgesel olarak nitrosil klorür ilavesi ile başlar. Bu tür daha sonra bir baz ile oksime dönüştürülür ve hidroksilamin, keton içeren karvon verecek şekilde çıkarılır. [2]

 

Bitkilerde
D-Limonene, çok sayıda iğne yapraklı ve geniş yapraklı ağaç için karakteristik aromatik koku ve reçinelerin önemli bir bileşenidir: kırmızı ve gümüş akçaağaç (Acer rubrum, Acer saccharinum), cottonwoods (Populus angustifolia), aspens (Populus grandidentata, Populus tremuloides) sumak (Rhus glabra), ladin (Picea spp.), çeşitli çamlar (örnekler, Pinus echinata, Pinus ponderosa), Douglas köknar (Pseudotsuga menziesii), karaçamlar (Larix spp.), gerçek köknar (Abies spp.), hemlocks (Tsuga spp.) , esrar (Cannabis sativa spp.), [9] sedirler (Cedrus spp.), çeşitli Cupressaceae ve ardıç çalı (Juniperus spp.). [1] Portakal kabuğu, portakal suyu ve diğer turunçgillerin karakteristik kokusuna katkıda bulunur. [1] [10] Narenciye kabuğu atıklarından değerli bileşenlerin geri kazanımını optimize etmek için, d-limonen tipik olarak uzaklaştırılır. [11]

 

 

IUPAC Adı
(4R) -1-metil-4-prop-1-en-2-ylcyclohexene

 

 

Moleküler formül
C10H16

 

 

Fiziksel tanım
FİZİKSEL TANIMLAMA: Limon benzeri hoş bir kokuya sahip, berrak, renksiz mobil sıvı.

 

 

Koku
Turunçgil kokusu

 

 

Damak zevki
TAZE, CITRUS TAT

 

Limonene, (+) - doğal bir siklik monoterpen ve potansiyel kemopreventif ve antitümör aktiviteleri olan turunçgil soyulmasından elde edilen yağın ana bileşenini içeren oral bir besin takviyesidir. Hareket mekanizması henüz tam olarak aydınlatılmamış olsa da, limonen ve metabolitleri perillik asit, dihidroperillik asit, üroterpenol ve limonen 1,2-diol, p21'e bağımlı sinyallemenin inhibisyonu yoluyla tümörün büyümesini inhibe edebilir ve apoptozu indüksiyon yoluyla indükleyebilir Dönüştürücü büyüme faktörü beta sinyal yolağı. Buna ek olarak, sinyal transdüksiyon proteinlerinin translasyon sonrası modifikasyonunu inhibe ederek G1 hücre döngüsünün durdurulmasına ve hücre döngüsü ile apoptoz ile ilgili genlerin diferansiyel ekspresyonuna neden olurlar.

Limonen, oda sıcaklığında berrak renksiz bir sıvıya sahip monoterpen olup, portakal yağı içindeki ana bileşen olan doğal olarak oluşan bir kimyasaltır. Limonen yaygın olarak bir lezzet ve koku olarak kullanılmaktadır ve Gıda ve İlaç İdaresi tarafından gıda güvenliğinde genel olarak kabul edilmektedir (Federal Yönetmelikler, ABD A, 21 CFR 182. 60). Limonen, düşük toksikli bir botanik (bitki kökenli) çözücüdür. Limonene maruz kaldıklarında hafif cilt tahrişi meydana gelebilir ve limonenin oksidasyon ürünleri dermal sensitizasyona neden olabilir ve tahriş edici ve bronkonstriktif hava yolu etkilerine sahip olabilir; Bununla birlikte, veriler yetersizdir ve daha fazla çalışma gerekmektedir. Limonenin sıçan spesifik bir böbrek toksisitesinin hiyal damla nefropatisi olarak adlandırılan bir erkek olmasına neden olduğu gösterilmiştir. Ayrıca, limonene kronik maruz kalma, yalnızca erkek sıçanlarda renal tübüler tümörlerin önemli bir insidansına neden olur. Limonen, kansere karşı koruyucu görünen diyette kullanılan fitokimyasal maddelerin aktif bileşenlerinden biridir. (PMID: 16563357, 15499193, 15325315, 2024047).

 


FİZİKSEL TANIMLAMA: Limon benzeri hoş bir kokuya sahip berrak renksiz seyyar sıvı

 

D-Limonene, yüksek seviyelerde limonlarda (adını türettiği) bulunan bir molekül, aynı zamanda çoğu narenciye gıdasıdır. Bir anti-kanser ajanı olarak vaat ediyor ve bazı nedenlerden dolayı yağ yakıcı etkilere dair minimum kanıt olmasına rağmen yağ yakıcı olarak pazarlanıyor. Hamur limon suyu ile tüketilebilir.

Monoterpen d-limonen, portakal yağı içindeki ana bileşen olan doğal olarak oluşan bir kimyasaltır. Şu anda, d-limonen yaygın olarak bir lezzet ve koku olarak kullanılmaktadır ve Gıda ve İlaç İdaresi tarafından gıda güvenliği açısından genel olarak kabul edilmektedir. Bununla birlikte, son zamanlarda, d-limonenin hiyalin damla nefropatisi olarak adlandırılan bir erkek sıçan spesifik böbrek toksisitesine neden olduğu gösterilmiştir. Ayrıca, d-limonene kronik maruz kalma, sadece erkek sıçanlarda renal tübüler tümörlerin önemli bir insidansına neden olur. d-limonen dişi sıçanlarda ya da daha yüksek dozajlar belirli bir erkek ve dişi farelerde kanserojen değildir, ancak, d-limonen, erkek sıçan spesifik nephrocarcinogenicity insan tüketimi d-limonen güvenliği ile ilgili bazı endişeler yükseltebilir. Bilimsel verilerin önemli bir kısmı, d-limonenin böbrek toksisitesinin, erkek sıçan böbrek proksimal tübü lizozomlannda bir protein, alfa 2u-globulinin birikiminden kaynaklandığını gösterdi. Bu protein sadece yetişkin erkek sıçanlar tarafından sentezlenir. İnsanlar da dahil olmak üzere diğer türler, alfa 2u-globulin ile önemli homoloji paylaşan proteinleri sentezler. Bununla birlikte, alfa 2u-globulin'in fare eşdeğeri de dahil olmak üzere bu proteinlerin hiçbiri, bu toksisiteyi üretebilir, bu da alfa 2u-globulin için eşsiz bir özgüllüğü belirtir. d-limonen kronik maruz kalma ile, hiyalin damlacık nefropati ilerler ve böbrek boru şekilli hücre nekrozu kortikomedüller kavşakta granül kast ve telafi edici hücre proliferasyonunu gösterir. Hem d-limonen hem de cis-d-limonen-1,2-oksit (bu toksisiteye katılan başlıca metabolit) in vitro mutajenisite ekranlarında negatiftir. Bu nedenle, toksisite ile ilgili renal hücre çoğalması böbrek hücre çoğalmasında sürekli artışlar kendiliğinden değiştirilmiş DNA'nın tespit arttırmak veya doğal olarak başlatılan hücreleri desteklemek için hizmet edebilir olarak, d-limonen kanserojen bütünleyici olarak yer olduğuna inanılmaktadır. Bilimsel veri tabanı, d-limonenin erkek sıçanlarda tümöre özgü etkinliğinin insanlar için geçerli olmadığını göstermektedir. D-limonenin insan güvenliğini destekleyen üç temel kanıt kanalı nefrotoksisite ve karsinojenisitenin erkek sıçan özgüllüğüdür; Yapısal olarak benzer proteinlerin varlığına rağmen diğer türlerde toksisitenin eksikliği ile kanıtlandığı üzere, alfa 2u-globulinin toksisite içerisinde oynadığı önemli rol; Ve hem d-limonene hem de d-limonene-1,2-oksidin genotoksisitesinin olmaması, nongenotoksik bir mekanizmanın, yani sürekli böbrek hücresi çoğalması kavramının desteklenmesidir.

Bu bileşik, mentan monoterpenoidleri olarak bilinen kimyasal varlık sınıfına aittir. Bunlar o-, m- veya p-mentan omurgasına dayanan bir yapıya sahip monoterpenoidlerdir. P-mentan sırasıyla 1 ve 4 halka konumunda bir metil grubu ve bir (2-metil) -propil grubu olan sikloheksan halkasından oluşur. O- ve mentanonlar çok daha nadirdir ve muhtemelen p-menthanelerin alkil migrasyonuyla ortaya çıkar.

 

 


Limonène

 

 

Structure du R-Limonène
Identification
Nom UICPA 1-méthyl-4-prop-1-èn-2-yl-cyclohexène
No CAS 5989-27-5 (R)
5989-54-8 (S)(-)
138-86-3 (RS)
No ECHA 100.028.848
No CE 227-813-5 (R)
227-815-6 (-)
PubChem 440917 [archive]
FEMA 2633
Apparence liquide incolore, d'odeur caractéristique. (d-limonene)1
Propriétés chimiques
Formule brute C10H16 [Isomères]
Masse molaire2 136,234 ± 0,0091 g/mol
C 88,16 %, H 11,84 %,
Propriétés physiques
T° fusion -75 °C (d-limonene)1
T° ébullition 176 °C (d-limonene)1
Solubilité dans l'eau : nulle (d-limonene)1
Masse volumique 0,84 g·cm-3 (d-limonene)1
T° d'auto-inflammation 255 °C
Point d'éclair 48 °C (d-limonene)1
Limites d'explosivité dans l'air 0,7-6,1 %vol
Pression de vapeur saturante à 14,4 °C : 0,4 kPa (d-limonène)1
Thermochimie
Cp 
[+]
Propriétés optiques
Pouvoir rotatoire (+)-limonène : +10 6 °·dm-1·l·g-1 (-)-limonène : -10 6 °·dm-1·l·g-1
Précautions
SGH5
SGH02 : InflammableSGH07 : Toxique, irritant, sensibilisant, narcotiqueSGH09 : Danger pour le milieu aquatique
Attention
H226, H315, H317, H410,
[+]
SIMDUT6,7,8
Limonène :
B3 : Liquide combustibleD2B : Matière toxique ayant d'autres effets toxiques
B3, D2B,
[+]
Limonène (d-) :
B3 : Liquide combustibleD2B : Matière toxique ayant d'autres effets toxiques
B3, D2B,
[+]
Limonène (l-) :
B3 : Liquide combustibleD2B : Matière toxique ayant d'autres effets toxiques
B3, D2B,
[+]
NFPA 704
RS :
Symbole NFPA 704

 

 

220
Classification du CIRC
Groupe 3 : Inclassable quant à sa cancérogénicité pour l'Homme4
Unités du SI et CNTP, sauf indication contraire.
modifier Consultez la documentation du modèle
Le limonène C10H16 est un hydrocarbure terpénique présent dans de nombreuses huiles essentielles à partir desquelles il peut être obtenu par distillation. À température ambiante, c'est un liquide incolore à odeur brillante, fraîche et propre d'orange, caractéristique des agrumes. Le limonène est notamment utilisé en parfumerie.

 

Le limonène tire son nom du citron qui, comme les autres agrumes, contient des quantités considérables de ce composé chimique, responsable en grande partie de leur parfum.

Le limonène est une molécule chirale, et, comme pour beaucoup de molécules chirales, les sources biologiques produisent un énantiomère spécifique. La principale source industrielle, l'orange, contient du D-limonène ((+)-limonène), qui est l'énantiomère R dextrogyre9. L'eucalyptus et la menthe poivrée, quant à eux, contiennent du L (-)-limonène, qui est l'énantiomère S lévogyre10,11. Le limonène racémique est connu en tant que dipentène12.

 


Sommaire
1 Utilisations
2 Chimie
3 Biosynthèse
4 Sécurité / Santé
5 Notes et références
5.1 Sources
6 Annexes
6.1 Articles connexes
6.2 Liens externes
Utilisations
Comme l'odeur principale qui constitue les agrumes (famille des Rutaceae), le D-limonène est utilisé dans l'industrie agroalimentaire ainsi que dans l'industrie pharmaceutique pour parfumer les médicaments, notamment les alcaloïdes amers. Il est également utilisé dans les produits nettoyants pour son odeur rafraîchissante orange-citron et son effet dissolvant.

 

Ainsi, le limonène est également de plus en plus utilisé comme solvant, notamment le dégraissage des machines, puisqu'il est produit depuis une source renouvelable, l'huile de citrus, comme un sous-produit de la fabrication de jus d'orange. Le limonène fonctionne comme solvant à peinture lorsqu'elle est appliquée sur du bois.

L'énantiomère R est également utilisé comme insecticide.

L'énantiomère S (ou L-limonène) a une odeur plus proche du pin et de la térébenthine.

L'utilisation du limonène est très fréquente dans les produits cosmétiques.

 

Chimie
Le limonène est un terpène relativement stable, qui peut être distillé sans décomposition, et forme de l'isoprène lorsqu'on le fait passer sur un filament de métal chaud. Il est facilement oxydé en environnement humide en carvéol et en carvone13. L'oxydation à l'aide du soufre produit du p-cymène et un sulfure.

 

 


Énantiomères R et S du limonène.
Le limonène existe naturellement comme (R)-énantiomère, mais peut être racémisé en dipentène, en le chauffant simplement à 300 °C. Lorsqu'il est chauffé avec un acide minéral, le limonène forme un diène conjugué, l'α-terpinène, qui s'oxyde facilement en p-cymène, un hydrocarbure aromatique. La preuve est en la formation d'α-terpinène résultant d'une réaction de Diels-Alder lorsque le limonène est chauffé avec de l'anhydride maléique.

 

Il est possible d'effectuer la réaction sur l'une des deux liaisons sélectivement. Le chlorure d'hydrogène anhydre réagit préférentiellement sur l'alcène disubstitué, alors que l'époxydation avec l'MCPBA se fait sur l'alcène trisubstitué. Dans les deux cas il est également possible de faire réagir l'autre double liaison.

Dans une autre méthode synthétique, l'addition Markovnikov d'acide trifluoroacétique suivie de l'hydrolyse de l'acétate donne du terpinéol.

 

Biosynthèse
Le limonène est formé à partir de géranyl-pyrophosphate, via une cyclisation d'un néryle carbocation ou son équivalent, comme montré ci-dessous14. L'ultime étape inclut la perte d'un proton par le cation pour former l'alcène.

 

 

d-Limonène
Numéro CAS : 5989-27-5

 

 

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Identification
Description

 

 

Numéro UN : UN2052
Formule moléculaire brute : C10H16

 

 

Principaux synonymes
Noms français :

 

 

(+)-4-Isopropenyl-1-méthylcyclohexène
(+)-Isopropenyl-4 méthyl-1 cyclohexène
(+)-Limonène
(+)-P-MENTHA-1,8-DIENE
(D)-Limonene
(R)-(+)-Limonene
(R)-(+)-P-Mentha-1,8-diene
(R)-1-Methyl-4-(1-methylethenyl)cyclohexene
(R)-4-Isopropenyl-1-methylcyclohexene
Carvene
CYCLOHEXENE, 1-METHYL-4-(1-METHYLETHENYL)-, (R)-
D-(+)-Limonène
D-Isopropenyl-4 méthyl-1 cyclohexène
d-Limonène
Limonène (d-)
Limonène, (+)-
R-1,8(9)-P-Menthadiene
Noms anglais :

 

 

(+)-4-Isopropenyl-1-methylcyclohexene
(+)-Limonene
D-(+)-Limonene
d-Limonene
Famille chimique
Terpène
Commentaires 1 2
Le limonène existe sous deux formes isomériques (d- et l- limonène) qui sont des images miroir l'une de l'autre. Le d-limonène est un constituant naturel de certains arbres, plantes, fruits et légumes. On le retrouve entre autres dans la pelure des agrumes (orange, citron, lime, etc.), les cornichons, le céleri, dans l'huile d'orange et dans plusieurs huiles essentielles. L'autre isomère (l-limonène) se retrouve principalement dans les huiles de pin, la térébenthine et les huiles de menthe. Le mélange, en proportions égales, des deux isomères est souvent appelé dipentène.

 

La concentration du d-limonène dans le produit commercial varie en général entre 60 et 98 %, selon le secteur d'activité où il est utilisé; les autres composants du mélange sont habituellement de type terpènes ainsi que des aldéhydes (octanal, nonanal, décanal) et alcools (linalool, etc.).

Comme le d-limonène est présent dans plusieurs plantes et aliments, il a été estimé que l'air intérieur pouvait causer l'équivalent d'une exposition à environ 10 µg/kg poids corporel/jour, alors que l'air extérieur pourrait équivaloir à une exposition à environ 0,1 µg/kg poids corporel/jour, et que la nourriture pouvait générer une exposition à environ 0,25 mg/kg poids corporel/jour.

 

Utilisation et sources d'émission 1 3 4 5 6
Le d-limonène est utilisé comme

 

 

agent dégraisseur des métaux et des machineries (industries de l'électronique et de l'imprimerie)
agent de saveur dans les aliments, les boissons non-alcoolisées et la gomme à mâcher
arôme dans les savons, les parfums et les produits d'entretien ménager
agent de mouillage et agent dispersant dans l'industrie des résines
solvant dans les peintures
agent nettoyant / dégraisseur dans les produits d'entretien ménager et industriel
solvant pour les produits d'esthétique
Références

 

 

Le d-limonène est un hydrocarbure liquide appartenant à la famille des terpènes. Il est
produit naturellement par divers végétaux, notamment les agrumes et représente le
constituant principal des huiles extraites des pelures de ces fruits. Utilisé depuis cinquante
ans comme arôme et flaveur, il prend maintenant depuis quelques années une importance
croissante comme nettoyant et dégraissant. On le retrouve dans de nombreuses
applications, notamment dans l'entretien mécanique, la fabrication de produits métalliques,
le nettoyage du fuselage des avions et le nettoyage des modules de circuits imprimés.
Rarement utilisé pur, il est formulé soit avec un agent tensioactif pour faciliter le rinçage à
l'eau, soit en émulsion dans l'eau, soit en mélange avec un ou plusieurs autres solvants.
L'application se fait par immersion, aspersion, pulvérisation ou au chiffon. Il est
généralement nécessaire de rincer à l'eau et de sécher les pièces. Quelques études
rapportent des niveaux d'exposition mesurés lors d'opérations de nettoyage/dégraissage qui
variaient généralement de 1 à 50 mg/m3
sur 8 heures, mais pouvant atteindre quelques
centaines de mg/m3
pour des opérations spécifiques de plus courte durée. Chez l'humain le
d-limonène est absorbé facilement par les poumons et de façon moindre par la peau. Il est
excrété principalement dans l'urine sous forme de composés hydroxylés conjugués. Le dlimonène est un irritant cutané; des dermites de contact allergiques peuvent se développer
lorsque le produit est dégradé par oxydation. La toxicité systémique du d-limonène est
considérée comme faible chez l'humain. Le produit n'est pas génotoxique, ni tératogène ou
foetotoxique. La cancérogénicité rénale observée chez certaines souches de rats mâles est
reliée à un mécanisme spécifique à ce sous-groupe d'animaux et non transposable à
l'humain. Bien qu'agréable, l'odeur du d-limonène semble constituer une gêne chez certains
travailleurs. La Suède a promulgué une valeur limite d'exposition professionnelle de 150
mg/m3
(25 ppm) sur 8 heures et 300 mg/m3
(50 ppm) sur 15 minutes. Son point d'éclair de
48 0
C fait qu'il est soumis à certaines restrictions quant à sa manipulation, son entreposage
et son transport afin d'éviter les risques d'incendie. Bien que le produit soit
photochimiquement réactif, ses effets sur l'environnement sont peu prononcés. Le
recyclage du d-limonène est difficilement réalisable dans le cas des nettoyants semiaqueux. L'ajout d'un antioxydant par le fabricant est essentiel pour prévenir sa dégradation
par auto-oxydation. Les récipients de d-limonène doivent toujours être couverts. Le port
de gants en caoutchouc (nitrile > butyle > alcool polyvinylique) est indispensable lors de sa
manipulation.

 

Le limonène C10H16 est un hydrocarbure terpénique présent dans de nombreuses huile_essentielle.phpe.phpentielle.php" title="Huiles essentielles" class="mw-redirect">huiles principales à partir desquelles il peut être obtenu par distillation. À température ambiante, c'est un liquide incolore à odeur brillante, fraîche et propre d'orange, caractéristique des agrumes. Le limonène est surtout utilisé en parfumerie.

Le limonène tire son nom du citron qui, comme les autres agrumes, contient des quantités énormes de ce composé chimique, responsable en grande partie de leur parfum.

Le limonène est une molécule chirale, et , comme pour énormément de molécules chirales, les sources biologiques produisent un énantiomère spécifique. La principale source industrielle, le citron, contient du D-limonène ( (+) -limonène), qui est le (R) -énantiomère[7]. Le limonène racémique est connu comme dipentène[8] La seconde forme est le L-limonène, qui est le (S) -énantiomère[9].

 


Utilisations
Comme l'odeur principale qui forme les agrumes (famille des Rutaceæ), le D-limonène est utilisé dans l'industrie agroalimentaire mais aussi dans l'industrie pharmaceutique pour parfumer les médicaments, surtout les alcaloïdes amères. Il est aussi utilisé dans les produits nettoyants pour son odeur rafraichissante orange-citron et son effet dissolvant.

 

Ainsi, le limonène est aussi de plus en plus utilisé comme solvant, surtout le dégraissage des machines, dans la mesure où il est produit depuis une source renouvelable, (l'huile de citrus, comme un sous-produit de la fabrication de jus d'orange). Le limonène fonctionne comme solvant à peinture quand elle est appliquée sur du bois.

Le (R) -énantiomère est aussi utilisé comme insecticide.

Le (S) -énantiomère, le l-limonène, a lui une odeur plus proche du pin et de la térébenthine.

L'utilisation du limonène est particulièrement fréquente dans les produits cosmétiques.

 


Chimie
Le limonène est un terpène assez stable, qui peut être distillé sans décomposition, et forme de l'isoprène quand on le fait passer sur un filament de métal chaud. Il est aisément oxydé en environnement humide en carvéol et en carvone[10]. L'oxydation à l'aide du soufre produit du p-cymène et un sulfure.

 

 


R et S énantiomères du limonène.
Le limonène existe naturellement comme (R) -énantiomère, mais peut être racémisé en dipentène, en le chauffant simplement à 300 °C. Quand il est chauffé avec un acide minéral, le limonène forme un diène conjugué, l'α-terpinène, qui s'oxyde aisément en p-cymène, un hydrocarbure aromatique. La preuve est en la formation d'α-terpinène résultant d'une réaction de Diels-Alder quand le limonène est chauffé avec de l'anhydride maléique.

 

Le limonène est envisageable d'effectuer la réaction sur l'une des deux liaisons sélectivement. Le chlorure d'hydrogène anhydre réagit préférentiellement sur l'alcène disubstitué, tandis que l'époxydation avec l'MCPBA se fait sur l'alcène trisubstitué. Dans les deux cas il est aussi envisageable de faire réagir l'autre double liaison.

Dans une autre méthode synthétique, l'addition Markovnikov d'acide trifluoroacétique suivie de l'hydrolyse de l'acétate donne du terpinéol.

 


Biosynthèse
Le limonène est constitué à partir de geranyl-pyrophosphate, via une cyclisation d'un neryl carbocation ou son équivalent, comme montré ci-dessous[11]. L'ultime étape inclut la perte d'un proton par le cation pour former l'alcène.

 

 

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