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

D-LIMONENE

D-LIMONENE

CAS NO: 5989-27-5


METATAGS;(+)-(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

 

EC Numarası: 227-813-5

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.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

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.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Acar Kimya A.Ş. © 2015 Tüm Hakları Saklıdır.