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GLYOXYLIC ACID (GLİOKSİLİK ASİT)


GLYOXYLIC ACID (GLİOKSİLİK ASİT)

 

CAS Number:298-12-4

EC Number:206-058-5

 

 

SYNONMYS

Glyoxylic acid monohydrate 98%; Formylformic acid, Oxoethanoic acid; MDL number MFCD00149497; Molecular Weight 92.05; Linear Formula HCOCO2H · H2O; Substance ID 24895036; glyoxalic acid; glyoxylate; glyoxylic acid; glyoxylic acid, 14C2-labeled; glyoxylic acid, 2-(14)C-labeled; glyoxylic acid, calcium salt; glyoxylic acid, sodium salt; glyoxylic acid, sodium salt, 14C-labeled; glyoxylic acid, sodium salt, 2-(14)C-labeled; glyoxylic acid; 298-12-4; 2-Oxoacetic Acid; Glyoxalic acid; Oxoacetic acid; Oxoethanoic acid; Formylformic acid; Acetic acid, oxo-; Oxalaldehydic acid; alpha-Ketoacetic acid; 2-Oxoacetic acid(50% in water); Formic acid, formyl-; glyoxalate; oxaldehydic acid; Kyselina glyoxylova; GLYOXALATE, GLYOXYLATE; Acetic acid, 2-oxo-; CCRIS 1455; HSDB 5559; Oxo-acetic acid; 563-96-2; Kyselina glyoxylova [Czech]; UNII-JQ39C92HH6; NSC 27785; OCHCOOH; .alpha.-Ketoacetic acid; EINECS 206-058-5; BRN0741891; CHEBI:16891; HHLFWLYXYJOTON-UHFFFAOYSA-N; glyox; oxoacetate; NSC27785; MFCD00006958; glyoxalic acid hydrate; GLV; formylformic; Formylformate; Glyoxalsaeure; Glyoxylsaeure; Oxalaldehydate; Oxoethanoate; glyoxilic acid; a-Ketoacetate; formyl-formicaci; aldehydoformicacid; alpha-Ketoacetate; 2-Oxoacetate ; (oxo)acetic acid; a-Ketoacetic acid; Acetic acid, oxo; alpha-ketoaceticacid; Formic acid, formyl; OHCCO2H; Glyoxylic acid (8CI); WLN: VHVQ; glyoxylicacid(50%orless); D0U9EW; AC1L19YQ; AC1Q71YA; AC1Q71YB; Acetic acid, oxo- (9CI); glyoxylicacid(oxo-aceticacid); 4-03-00-01489 (Beilstein Handbook Reference); KSC201S7T; GLYOXYLIC ACID CRYS..; Glyoxylic acid, 50% in water; JQ39C92HH6; CHEMBL1162545; DTXSID5021594; BDBM19472; CTK1A1979; Glyoxylic acid (50% in water); KS-00000QWZ; 2990-19-4 (calcium salt); MolPort-001-788-315; EBD11505; KS-00000KI7; ZINC4658554; 2706-75-4 (hydrochloride salt); ANW-26704; Glyoxylic acid, 50% w/w aq. soln; NSC-27785; STL168883; AKOS005367012; DB04343; MCULE-5307898766; RL03029; RTR-012899; AJ-51836; AK-48128; AK109361; AN-23352
BC679582; BR-48128; LS-73000; OR034470; OR254685; SC-18712; SC-25819; Glyoxylic Acid Solution, 50wt.% in H2O; KB-254206; ST2410189; TR-012899; FT-0626797; G0366; Glyoxylic acid solution, 50 wt. % in H2O; ST24040983; W5228; C00048; Glyoxylic acid solution, purum, ~50% in H2O; 78606-EP2295432A1; 78606-EP2308847A1Glyoxylic acid solution, 50 wt. % in water 250g; I04-0231; W-105518; I14-19186; F2191-0150; 0ADD8E81-5E77-4171-9241-E74AC05D4C8D; 872051-56-4; 298-12-4 [RN]Acetic acid, 2-oxo- [ACD/Index Name]; Acide glyoxyl [French] [ACD/IUPAC Name]; Acide glyoxylique [French]; a-Ketoacetic acid; Glyoxyl acid [ACD/IUPAC Name]Glyoxylic acid [Wiki]; Glyoxylsäure [German]; Oxoacetic acid; Oxoessigsäure [German] [ACD/IUPAC Name]; 206-058-5 [EINECS]; 2-Oxo acid; 2-Oxoacetic Acid; 2-Oxoacetic acid(in water); 4-03-00-01489 (Beilstein Handbook Reference) [Beilstein]; 741891 [Beilstein]; Acetic acid, oxo-; Acetic acid, oxo- (9CI); BR-48128Formic acid, formyl; Formic acid, formyl-; formylformic acid; Formylformic acid monohydrate; GLV; Glycoxylic acid; glyox; Glyoxalic acid; glyoxalic acid hydrate; Glyoxalsaeure; Glyoxylic acid (8CI); Glyoxylsaeure; JQ39C92HH6; Kyselina glyoxylova [Czech]; oxalaldehydic acid; oxaldehydic acid; oxaldehydic acid hydrate; Oxalic acid [ACD/IUPAC Name] [Wiki]; OXD; Oxo-acetic acid; OXOETHANOIC ACID; Oxoethanoic acid monohydrate; UNII:JQ39C92HH6; UNII-JQ39C92HH6; WLN: VHVQ; ?-ketoacetic acid; ?-ketoacetic acid; ?-Ketoacetic acid; ??? [Chinese]; Acetic acid, 2-oxo-, hydrate (1:1) [ACD/Index Name]; Acide oxoacétique, hydrate (1:1) [French] [ACD/IUPAC Name]; Glyoxylic acid monohydrate [Wiki]; Oxoacetic acid hydrate (1:1) [ACD/IUPAC Name]; Oxoessigsäurehydrat (1:1) [German] [ACD/IUPAC Name]; [563-96-2]; 1152495-30-1 [RN]; 206-058-5 [EINECS]; 298-12-4 [RN]; 2-Methylpropanamide [ACD/IUPAC Name]; 2-Oxoacetic Acid; 2-Oxoacetic acid hydrate; 2-Oxoacetic acid monohydrate; 2-Oxoethanoic acid monohydrate; 563-96-2 [RN]; 6000-59-5 [RN]; formylformic acid; Formylformic acid monohydrate; Glyoxalic acid; glyoxalic acid hydrate; Glyoxalic acid hydrate;Glyoxylic acid monohydrate; Glyoxalic Acid Monohydrate; Glyoxylic Acid Hydrate; Glyoxylic acid monohydrate, Formylformic acid monohydrate, 2-Oxoethanoic acid monohydrate; Glyoxylic acid monohydrate; Formylformic acid monohydrate; 2-Oxoethanoic acid monohydrate; Glyoxylic acid monohydrate; Formylformic acid monohydrate; 2-Oxoethanoic acid monohydrate; 563-96-2 (diol); glyoxylicacidhydrate; Glyoxylicacidmonohydrate; oxaldehydic acid and hydrate; oxoacetate monohydrate; oxoacetic acid hydrate; Oxoacetic acid monohydrate; Oxoacetic acid--water (1/1); OXOETHANOIC ACID; QA-1237; glyoxylic; InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5); GA;OCHCOOH;Glyoxalate;glyoxylate;Glyoxylsure;Formylformic;oxo-aceticaci;GLYOXALIC ACID;GLYOXYLIC ACID;oxo-acetic acid; CHEBI:42767, CHEBI:5509, CHEBI:24421; InChI?=?1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5); InChIKey?=?HHLFWLYXYJOTON-UHFFFAOYSA-N; Glyoxylic acid monohydrate for synthesis. ; Oxoethanoic acid, Oxoacetic acid, Acetic acid, Oxo-, Glyoxalic acid; Glyoxylic acid; glyoxylic acid; oxaldehydic acid; glyoxalate; glyoxylic acid; oxoacetic acid glyoxalic acid; Exchange reactions, glyoxal oxidation, glyoxylic acid, selective separation, sodium glyoxylate; Glyoxylic acid ... ; Glyoxylic Acid Monohydrate 98%; oxoacetic acid; Glyoxylic oxime acid, bis(trimethylsilyl)-; InChI=1S/C8H19NO3Si2/c1-13(2,3)11-8(10)7-9-12-14(4,5)6/h7H,1-6H3; Glyoxylic acid, oxime, bis-TMS; Glyoxylic acid, oxime, di-TMS; Glyoxylic oxime, bis-TMS; Glyoxylic oxime, (2TMS); Glyoxylic oxime, TMS; Glycolic acid, oxime, TMS; Oximated glyoxylic acid, diTMS; Glyoxylic Acid ;Glyoxylic acid monohydrate 98%; Formylformic acid, Oxoethanoic acid; MDL number MFCD00149497; Molecular Weight 92.05; Linear Formula HCOCO2H · H2O; Substance ID 24895036; glyoxalic acid; glyoxylate; glyoxylic acid; glyoxylic acid, 14C2-labeled; glyoxylic acid, 2-(14)C-labeled; glyoxylic acid, calcium salt; glyoxylic acid, sodium salt; glyoxylic acid, sodium salt, 14C-labeled; glyoxylic acid, sodium salt, 2-(14)C-labeled; glyoxylic acid; 298-12-4; 2-Oxoacetic Acid; Glyoxalic acid; Oxoacetic acid; Oxoethanoic acid; Formylformic acid; Acetic acid, oxo-; Oxalaldehydic acid; alpha-Ketoacetic acid; 2-Oxoacetic acid(50% in water); Formic acid, formyl-; glyoxalate; oxaldehydic acid; Kyselina glyoxylova; GLYOXALATE, GLYOXYLATE; Acetic acid, 2-oxo-; CCRIS 1455; HSDB 5559; Oxo-acetic acid; 563-96-2; Kyselina glyoxylova [Czech]; UNII-JQ39C92HH6; NSC 27785; OCHCOOH; .alpha.-Ketoacetic acid; EINECS 206-058-5; BRN0741891; CHEBI:16891; HHLFWLYXYJOTON-UHFFFAOYSA-N; glyox; oxoacetate; NSC27785; MFCD00006958; glyoxalic acid hydrate; GLV; formylformic; Formylformate; Glyoxalsaeure; Glyoxylsaeure; Oxalaldehydate; Oxoethanoate; glyoxilic acid; a-Ketoacetate; formyl-formicaci; aldehydoformicacid; alpha-Ketoacetate; 2-Oxoacetate ; (oxo)acetic acid; a-Ketoacetic acid; Acetic acid, oxo; alpha-ketoaceticacid; Formic acid, formyl; OHCCO2H; Glyoxylic acid (8CI); WLN: VHVQ; glyoxylicacid(50%orless); D0U9EW; AC1L19YQ; AC1Q71YA; AC1Q71YB; Acetic acid, oxo- (9CI); glyoxylicacid(oxo-aceticacid); 4-03-00-01489 (Beilstein Handbook Reference); KSC201S7T; GLYOXYLIC ACID CRYS..; Glyoxylic acid, 50% in water; JQ39C92HH6; CHEMBL1162545; DTXSID5021594; BDBM19472; CTK1A1979; Glyoxylic acid (50% in water); KS-00000QWZ; 2990-19-4 (calcium salt); MolPort-001-788-315; EBD11505; KS-00000KI7; ZINC4658554; 2706-75-4 (hydrochloride salt); ANW-26704; Glyoxylic acid, 50% w/w aq. soln; NSC-27785; STL168883; AKOS005367012; DB04343; MCULE-5307898766; RL03029; RTR-012899; AJ-51836; AK-48128; AK109361; AN-23352BC679582; BR-48128; LS-73000; OR034470; OR254685; SC-18712; SC-25819; Glyoxylic Acid Solution, 50wt.% in H2O; KB-254206; ST2410189; TR-012899; FT-0626797; G0366; Glyoxylic acid solution, 50 wt. % in H2O; ST24040983; W5228; C00048; Glyoxylic acid solution, purum, ~50% in H2O; 78606-EP2295432A1; 78606-EP2308847A1Glyoxylic acid solution, 50 wt. % in water 250g; I04-0231; W-105518; I14-19186; F2191-0150; 0ADD8E81-5E77-4171-9241-E74AC05D4C8D; 872051-56-4; 298-12-[RN Acetic acid, 2-oxo- [ACD/Index Name]; Acide glyoxyl [French] [ACD/IUPAC Name]; Acide glyoxylique [French]; a-Ketoacetic acid; Glyoxyl acid [ACD/IUPAC Name]Glyoxylic acid [Wiki]; Glyoxylsäure [German]; Oxoacetic acid; Oxoessigsäure [German] [ACD/IUPAC Name]; 206-058-5 [EINECS]; 2-Oxo acid; 2-Oxoacetic Acid; 2-Oxoacetic acid(in water); 4-03-00-01489 (Beilstein Handbook Reference) [Beilstein]; 741891 [Beilstein]; Acetic acid, oxo-; Acetic acid, oxo- (9CI); BR-48128Formic acid, formyl; Formic acid, formyl-; formylformic acid; Formylformic acid monohydrate; GLV; Glycoxylic acid; glyox; Glyoxalic acid; glyoxalicacidhydrate; Glyoxalsaeure; Glyoxylic acid (8CI); Glyoxylsaeure; JQ39C92HH6; Kyselina glyoxylova [Czech]; oxalaldehydic acid; oxaldehydic acid; oxaldehydic acid hydrate; Oxalic acid [ACD/IUPAC Name] [Wiki]; OXD; Oxo-acetic acid; OXOETHANOIC ACID; Oxoethanoic acid monohydrate; UNII:JQ39C92HH6; UNII-JQ39C92HH6; WLN: VHVQ; ?-ketoacetic acid; ?-ketoacetic acid; ?-Ketoacetic acid; ??? [Chinese]; Acetic acid, 2-oxo-, hydrate (1:1) [ACD/Index Name]; Acide oxoacétique, hydrate (1:1) [French] [ACD/IUPAC Name]; Glyoxylic acid monohydrate [Wiki]; Oxoacetic acid hydrate (1:1) [ACD/IUPAC Name]; Oxoessigsäurehydrat (1:1) [German] [ACD/IUPAC Name]; [563-96-2]; 1152495-30-1 [RN]; 206-058-5 [EINECS]; 298-12-4 [RN]; 2-Methylpropanamide [ACD/IUPAC Name]; 2-Oxoacetic Acid; 2-Oxoacetic acid hydrate; 2-Oxoacetic acid monohydrate; 2-Oxoethanoic acid monohydrate; 563-96-2 [RN]; 6000-59-5 [RN]; formylformic acid; Formylformic acid monohydrate; Glyoxalic acid; glyoxalic acid hydrate; Glyoxalic acid hydrate;Glyoxylic acid monohydrate; Glyoxalic Acid Monohydrate; Glyoxylic Acid Hydrate; Glyoxylic acid monohydrate, Formylformic acid monohydrate, 2-Oxoethanoic acid monohydrate; Glyoxylic acid monohydrate; Formylformic acid monohydrate; 2-Oxoethanoic acid monohydrate; Glyoxylic acid monohydrate; Formylformic acid monohydrate; 2-Oxoethanoic acid monohydrate; 563-96-2 (diol); glyoxylicacidhydrate; Glyoxylicacidmonohydrate; oxaldehydic acid and hydrate; oxoacetate monohydrate; oxoacetic acid hydrate; Oxoacetic acid monohydrate;Oxoacetic acid--water (1/1); OXOETHANOIC ACID; QA-1237; glyoxylic; InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5);GA;OCHCOOH;Glyoxalate;glyoxylate;Glyoxylsure;Formylformic;oxo-aceticaci;GLYOXALIC ACID;GLYOXYLIC ACID;oxo-acetic acid; CHEBI:42767, CHEBI:5509, CHEBI:24421; InChI?=?1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5); InChIKey?=?HHLFWLYXYJOTON-UHFFFAOYSA-N; Glyoxylic acid monohydrate for synthesis. ; Oxoethanoic acid, Oxoacetic acid, Acetic acid, Oxo-, Glyoxalic acid; Glyoxylic acid; glyoxylic acid; oxaldehydic acid; glyoxalate; glyoxylic acid; oxoacetic acid glyoxalic acid; Exchange reactions, glyoxal oxidation, glyoxylic acid, selective separation, sodium glyoxylate; Glyoxylic acid ... ; Glyoxylic Acid Monohydrate 98%; oxoacetic acid; Glyoxylic oxime acid, bis(trimethylsilyl)-; InChI=1S/C8H19NO3Si2/c1-13(2,3)11-8(10)7-9-12-14(4,5)6/h7H,1-6H3; Glyoxylic acid, oxime, bis-TMS; Glyoxylic acid, oxime, di-TMS; Glyoxylic oxime, bis-TMS; Glyoxylic oxime, (2TMS); Glyoxylic oxime, TMS; Glycolic acid, oxime, TMS; Oximated glyoxylic acid, diTMS; Glyoxylic Acid ;GLYOXALIC ACID; GLYOXALİC ACİD; GLYOXALIİK ACİD; GLYOKSALİL ASİD; GLYOKSAL; GLİOKSAL; GLIOKSAL ASIT; GLYOXAL ACID; GLİOXAL ACİD; GLYOKSAL ACID; GLYOXAL ASİD; ASID; glyoksal asid; glioksal asid; glyoksal asid; glyoxal acıd; glyoxal acid; glioksal asit; glyoksal asıt; asıd; glioksal asıd; glıoksal asıd; glioksal asid; glyoxal acid;lyoxylic Acid (GXA) is a colorless solid and a highly reactive chemical intermediate having two functional groups: an aldehyde group and a carboxylic acid group.Glyoxylic Acid is soluble in water and ethanol, slightly soluble in organic solvents like ether or benzene, and insoluble in esters aromatic solvents.Aqueous solutions of Glyoxylic Acid are transparent, colorless or light yellow liquids.GXA is a strong organic acid (Ka=4.7x10-4), and due to its bifunctionality serves as an important C2 building block for many organic molecules of industrial importance. GXA is e.g. used in the production of agrochemicals, aromas, cosmetic ingredients, pharmaceutical intermediates and polymers.Glyoxylic Acid finds application in personal care as neutralizing agent, it is widely used in hair straightening products in particular (shampoos, conditioners, lotions, creams) at levels of 0.5-10%.

 

 

 Glikoksilik asitin özellikleri

Moleküler Formül: C2H2O3
Moleküler Ağırlık: 74.035 g / mol
Yoğunluk 1,34 g / cm3 (20 ° C)

 

 

 

 

  Glioksilik asit veya oksoasetik asit, hem bir aldehit hem de bir karboksilik asit olan organik bir bileşiktir. Glyoxylic asit -93 ° C erime noktasına ve 111 ° C kaynama noktasına sahip bir sıvıdır. Bazı organizmaların yağ asitlerini karbonhidratlara dönüştürmesini sağlayan glioksilat döngüsünün bir ara ürünüdür. Glikoksilik asitin konjuge tabanı, glioksilat (PMID: 16396466) olarak bilinir. İnsanlarda, glioksilat iki yolla üretilir: (1) peroksizomlarda glikolatın oksidasyonu ve (2) mitokondriyadaki hidroksiprolinin katabolizması. Peroksizomlarda, glioksilat, glioksilat aminotransferaz (AGT1) veya glikolat oksidaz ile oksalat ile glisin haline dönüştürülür. Mitokondride, glioksilat, glikoz içine mitokondriyal glioksilat aminotransferaz AGT2 veya glikolat ile glikolat redüktaz ile dönüştürülür. Az miktarda glioksilat, sitoplazmik laktat dehidrogenaz ile oksalat haline dönüştürülür. Glyoxylic asit, metabolizmanın doğuştan gelen bir hatası olan primer hyperoxaluria I ile ilişkili bulunmuştur. Belirli koşullar altında, glioksilat bir nefrotoksin ve bir metabotoksin olabilir. Bir nefrotoksin, böbrek ve böbrek dokularına zarar veren bir bileşiktir. Metabotoksin kronik olarak yüksek seviyelerde olumsuz sağlık etkilerine neden olan endojen olarak üretilmiş bir metabolittir. Yüksek düzeyde glioksilat, nefrolitiazisin (genellikle böbrek taşları olarak bilinir) temel bir nedeni olan hiperoksalurinin gelişiminde rol oynar. Glyoksilat, hem bir substrat ve hem de oksalat taşınmasından sorumlu bir gen olan sülfat anyonu taşıyıcısı-1 (SAT-1) indüktörünün bir indükleyicisidir ve SAT-1 mRNA ekspresyonunu ve bunun sonucunda hücreden oksalat akıntısını arttırır. Artan oksalat salımı, idrarda kalsiyum oksalatın birikmesine ve böylelikle de böbrek taşlarının oluşmasına izin verir. Bir aldehit olarak, glioksilat da oldukça reaktiftir ve proteinleri gelişmiş glikasyon ürünleri (AGE'ler) oluşturmak üzere değiştirecektir.

 

 

  Glioksilik asit (GA), doğal olarak oluşan ve iyonu ile olan renksiz bir katıdır. Glisoksilik asitin sulu çözeltisi saydam renksiz veya açık sarı bir sıvıdır. Suda ve etanolde çözünür, eter veya benzen gibi organik çözücüler içinde az çözünür, esterler aromatik çözücüler içinde çözmez. Bu çözelti oluşmuyor, havada bozunmayacak.

  GA, güçlü bir organik asit ve iki kimyasal madde içeren bir kimyasal madde maddesi: aldehit grubu ve karboksilik asit grubu. İki bileşenli organik ve ince kimyasallar sentezlerinde çok yönlü bir reaktiftir.

 

 

 

Uygulamalar:

Akımsız Bakır Kaplama

  Glyoxylic Acid, elektriksiz bakır kaplama için alternatif bir indirgeyici ajan olarak kullanılabilir. Kaplama oranları ve banyo stabilitesi, standart koşullar altında formaldehit banyosununkinden daha üstündür. Kaplama banyosundaki glioksilat iyonları, buhar basıncına sahip değildir ve elektriksiz bakır kaplamada iyi bir indirgeme gücü gösterir. Bu nedenle, glioksilik asit formaldehitin yerine geçebilir ve duman oluşumundan kaynaklanan sağlık ve çevre sorunlarını ortadan kaldırabilir.


Biyojenik Aminler Görüntüleyici

  GXA çeşitli yoğunlaşma reaksiyonlarına girebilir ve bu nedenle histolojik kesitlerde biyojenik aminlerin görsel olarak tespitinde yaygın olarak kullanılır. Bu floresan floresan mikroskobu ile analiz edildiği dokularda monoaminlerin görselleştirme için sükroz-fosfat-glioksilik asit (SPG) histofluoresans yöntemidir. Dokuları saymak için kullanılır.

 

 

Mantar ilaçları

  GXA türevleri yeni bir Oomycete fungisit sınıfı olarak tanımlanmıştır. GXA türevleri, üzümlerde (Plasmopara viticola) dwoni küfü ve patateslerde bir yanıklığı (Phytophthora infestans) içeren oomiselere karşı spesifik aktivite gösterir. Tacoco ve narenciyede Phytophthora gibi topraktaki Oomisetlere karşı aktiftirler. Koruyucu, iyileştirici, eradikatif ve antisporulan aktivitesi sergilerler. Bu bileşik sınıfı, ikinci aşamada glikolik asit esterinin gerekli olduğu basit bir sentetik yaklaşımla sentezlenebilir.

 

 

İlaç

  Gloxylic Acid ya bir ham maddedir veya D, Lp-hidroksifenilglisin, D, Lp-hidroksifenilhidantoin, orotik yardım, sulindak, mandelik asit, p-hidroksifenilasetik asit, difenilasetik asit, Lamivudin gibi çeşitli farmasötik ürünlerin sentezinde bir ara madde olarak kullanılır. 4-Aminofenilasetik asit.

 


Tarımsal Kimyasallar

  Glyoxylic Acid, örn. Etilen bis (hidroksifenil) glisin, glifosat, 2-hidroksi kinoksalin ve EDDHA gibi kompleksleştirici ajanlar.

 


Lezzet ve Koku Ürünleri

  Glyoxylic Acid, vanilin, etil vanilin ve heliotropin gibi farklı aromalar için önemli bir hammadde olarak kullanılabilir.

 


Kişisel Bakım Ürünleri Malzemeler

  GXA'dan üretilen çok önemli bir ürün, büyük ölçüde kozmetikte kullanılan Allantoin'dir. Glyoxylic Acid diüriti olarak düşünülebilir ve ciltte yumuşatıcı (keratolitik etki) ve hızlı hücre rejenerasyonunda yüksek oranda aktiftir.

 

Properties of glyoxylic acid


Molecular Formula:C2H2O3
Molecular Weight:74.035 g/mol
Density 1.34 g/cm3 (20 °C)

 

 

  Glyoxylic acid or oxoacetic acid is an organic compound that is both an aldehyde and a carboxylic acid. Glyoxylic acid is a liquid with a melting point of -93°C and a boiling point of 111°C. It is an intermediate of the glyoxylate cycle, which enables certain organisms to convert fatty acids into carbohydrates. The conjugate base of glyoxylic acid is known as glyoxylate (PMID: 16396466 ). In humans, glyoxylate is produced via two pathways: (1) through the oxidation of glycolate in peroxisomes and (2) through the catabolism of hydroxyproline in mitochondria. In the peroxisomes, glyoxylate is converted into glycine by glyoxylate aminotransferase (AGT1) or into oxalate by glycolate oxidase. In the mitochondria, glyoxylate is converted into glycine by mitochondrial glyoxylate aminotransferase AGT2 or into glycolate by glycolate reductase. A small amount of glyoxylate is converted into oxalate by cytoplasmic lactate dehydrogenase. Glyoxylic acid is found to be associated with primary hyperoxaluria I, which is an inborn error of metabolism. Under certain circumstances, glyoxylate can be a nephrotoxin and a metabotoxin. A nephrotoxin is a compound that causes damage to the kidney and kidney tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. High levels of glyoxylate are involved in the development of hyperoxaluria, a key cause of nephrolithiasis (commonly known as kidney stones). Glyoxylate is both a substrate and inductor of sulfate anion transporter-1 (SAT-1), a gene responsible for oxalate transportation, allowing it to increase SAT-1 mRNA expression, and as a result oxalate efflux from the cell. The increased oxalate release allows the buildup of calcium oxalate in the urine, and thus the eventual formation of kidney stones. As an aldehyde, glyoxylate is also highly reactive and will modify proteins to form advanced glycation products (AGEs).

 

 

  Glyoxylic acid (GA) is a colourless solid that occurs naturally and is useful industrially. Aqueous solution of Glyoxylic acid is transparent colorless or light yellow liquid. Soluble in water and ethanol, slightly soluble in organic solvents like ether or benzene, insoluble in esters aromatic solvents. This solution is not stable but will not decay in the air.

  GA is a strong organic acid and a highly reactive chemical intermediate having two functional groups: the aldehyde group and the carboxylic acid group. Because of its bi-functionality is a versatile reagent in organic and fine chemicals syntheses.

 

 

 

 

Applications:

Electroless Copper Plating

  Glyoxylic Acid can be used as an alternative reducing agent for electroless copper plating. Plating rates and bath stability were superior to that of the formaldehyde bath under standard conditions. Glyoxylate ions in the plating bath have no vapor pressure and show good reducing power in the electroless copper plating. Therefore, glyoxylic acid can replace formaldehyde, and eliminate health and environmental problems resulting from generation of the fumes.

 

 

Biogenic Amines Visualizer

  GXA can undergo various condensation reactions and thus is commonly used for visual detection of biogenic amines in histological sections. This is the sucrose-phosphate-glyoxylic acid (SPG) histofluorescence method for the visualization of monoamines in tissues where the fluorescence is analyzed by fluorescence microscopy. It is used for counterstaining tissues.

 

 

Fungicides

  GXA derivatives have been described as a new class of Oomycete fungicides. The GXA derivatives exhibit specific activity against oomycetes, including dwony mildew on grapes (Plasmopara viticola) and late blight on potatoes an tomatoes (Phytophthora infestans). They are active against Oomycetes in soil such as Phytophthora in tabacoo and citrus. They exhibit protective, curative, eradicative and antisporulant activity. This class of compounds can be synthesized via a simple synthetic approach where in the second step the glycolic acid ester is needed.

 

Pharmaceuticals

  Gloxylic Acid is either a raw material or used as an intermediate in the synthesis of various pharmaceutical products like D,L-p-hydroxyphenylglycine, D,L-p-hydroxyphenylhydantoin, orotic aid, sulindac, mandelic acid, p-hydroxyphenylacetic acid, diphenylacetic acid, Lamivudine and 4-Aminophenylacetic acid.


Agrochemicals

  Glyoxylic Acid is used as a key raw material for the synthesis of e.g. Ethylene bis(hydroxyphenyl)glycine, glyphosate, 2-hydroxy quinoxaline and complexing agents like EDDHA.

 

Flavor and Fragrance Products

  Glyoxylic Acid can be used as a key raw material for different aromas such as vanillin, ethyl vanillin and heliotropin.


Personal Care Products Ingredients

  A very prominent product produced from GXA is Allantoin which is used to a great extent in cosmetics. It can be considered as the diureide of Glyoxylic Acid and is highly active in skin-softening (keratolytic effect) and rapid cell regeneration by precipitating proteins on skin.

 

 

 


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