Glyoxylic acid

Base Information

• Chemical Name: Glyoxylic acid
• CAS No.: 298-12-4
• Deprecated CAS: 872051-56-4
• Molecular Formula: C2H2O3
• Molecular Weight: 74.0361
• Hs Code.: 29183000
• European Community (EC) Number: 206-058-5,679-230-4
• NSC Number: 27785
• UN Number: 3265
• UNII: JQ39C92HH6
• DSSTox Substance ID: DTXSID5021594
• Nikkaji Number: J38.150K
• Wikipedia: Glyoxylic_acid
• Wikidata: Q413552
• Metabolomics Workbench ID: 37082
• ChEMBL ID: CHEMBL1162545
• Mol file: 298-12-4.mol

Synonyms: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

Chemical Property of Glyoxylic acid

Chemical Property:

• Appearance/Colour: clear yellow solution
• Vapor Pressure: 0.0331mmHg at 25°C
• Melting Point: -93 °C
• Refractive Index: n20/D 1.414
• Boiling Point: 224.601 °C at 760 mmHg
• PKA: 3.18(at 25℃)
• Flash Point: 103.914 °C
• PSA: 54.37000
• Density: 1.384 g/cm³
• LogP: -0.73010
• Storage Temp.: 2-8°C
• Solubility.: Miscible with ethanol. Slightly miscible with ether and benzene.
• Water Solubility.: miscible
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 74.000393922
• Heavy Atom Count: 5
• Complexity: 55.9
• Transport DOT Label: Corrosive

Purity/Quality:

50%min ^*data from raw suppliers

GlyoxylicAcid(50%aqueoussolution) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: C,Xi
• Statements: 34-43-41
• Safety Statements: 26-36/37/39-45-37/39-24

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(=O)C(=O)O
• Uses: Glyoxalic acid can be used in the synthesis of a variety of reactions.Glyoxylic acid is used in Hopkins Cole reaction, which is used in the detection of tryptophan in proteins. It reacts with phenol to get 4-hydroxymandelic acid, which on further reaction with ammonia gives hydroxyphenylglycine, as a precursor to the drug amoxicillin. It is also used as a starting material for the preparation of 4-hydroxyphenylacetic acid, which is used to get atenolol.

Technology Process of Glyoxylic acid

There total 417 articles about Glyoxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(E)-3-phenylacrylic acid (140-10-3) → benzaldehyde (100-52-7) + Glyoxilic acid (298-12-4)

Guidance literature:

With potassium hexacyanoferrate(III); In perchloric acid; acetic acid; at 50 ℃; Mechanism; Kinetics; E_a, ΔH(excit.), ΔS(excit.), other temperatures, other concentrations acids;

Reference yield: 26.5%

ethylene glycol (107-21-1) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + Glyoxal (131543-46-9,107-22-2) + acetaldehyde (75-07-0,9002-91-9) + Glyoxilic acid (298-12-4)

Guidance literature:

With nitrogen; oxygen; iron(III) phosphate doped with Mo(VI); In water; at 310 ℃; Further byproducts given;

DOI:10.1246/bcsj.75.375

Reference yield:

3-(4-methoxybenzoyl)acrylic acid (5711-41-1) → Glyoxilic acid (298-12-4) + 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

upstream raw materials:

Hippuric Acid

diazoacetic acid ethyl ester

ethanol

diethylazodicarboxylate

Downstream raw materials:

(2E)-but-2-enedioic acid

(5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-(3-methyl-5-oxo-1-phenyl-1,5-dihydro-pyrazol-4-ylidene)-methane

bis-benzoylamino-acetic acid

2,2'-didimedonylacetic acid

Refernces

• 1、 Eggins, Brian R.,Irvine, John T. S.,Murphy, Eileen P.,Grimshaw, James. "Formation of Two-Carbon Acids from Carbon Dioxide by Photoreduction on Cadmium Sulphide". . p. 1123 - 1124. Retrieved 1988.
• 2、 Murray et al.. "-". . p. 2405. Retrieved 1952.
• 3、 Ai, Mamoru,Ohdan, Kyoji. "Formation of Glyoxylic Acid by Oxidative Dehydrogenation of Glycolic Acid". . p. 1995 - 2000. Retrieved 1997.
• 4、 Pal, Biswajit. "Mechanistic investigation of the oxidative cleavage of the carbon-carbon double bond in α,β-Unsaturated compounds by hexachloroiridate(iv) in acetate buffer". . p. 31 - 40. Retrieved 2014.
• 5、 Yamada, Miwa,Higashiyama, Takanori,Kishino, Shigenobu,Kataoka, Michihiko,Ogawa, Jun,Shimizu, Sakayu,Isobe, Kimiyasu. "Novel alcohol oxidase with glycolate oxidase activity from Ochrobactrum sp. AIU 033". . p. 41 - 48. Retrieved 2014.
• 6、 Liu, Junchi,Qin, Feng,Huang, Zhen,Huang, Liang,Liao, Zhenan,Xu, Hualong,Shen, Wei. "Selective Oxidation of Glyoxal to Glyoxalic Acid by Air over Mesoporous Silica Supported Pd Catalysts". . p. 1894 - 1902. Retrieved 2019.
• 7、 Skarlatos et al.. "-". . p. 2587,2590, 2591. Retrieved 1975.
• 8、 Kong, Kang,Li, Difan,Ma, Wenbao,Zhou, Qingqing,Tang, Guoping,Hou, Zhenshan. "Aluminum(III) triflate-catalyzed selective oxidation of glycerol to formic acid with hydrogen peroxide". . p. 534 - 542. Retrieved 2019.
• 9、 Vegad, Hiran,Lobell, Mario,Bornemann, Stephen,Crout, David H.G.. "Stereochemistry of the decarboxylation of glyoxylic acid by yeast pyruvate decarboxylase". . p. 2317 - 2324. Retrieved 2000.
• 10、 Abe, Yasuo,Horii, Hideo,Taniguchi, Setsuo,Kamai, Kazuo,Takagi, Masanosuke. "The Autoxidation of 2,3-Dihydroxy-2-propenal (Triose Reductone). The Effects of the pH on the Rate Constants". . p. 467 - 470. Retrieved 1983.