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Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C₂ carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially.

Structure and nomenclature

Glyoxylic acid is usually described with the chemical formula OCHCO₂H, i.e. containing an aldehyde functional group (see image in upper right). In fact the aldehyde is not observed in solution or as a solid. In general aldehydes with electron-withdrawing substituents often exist mainly as their hydrate. Thus, the formula for glyoxylic acid is really (HO)₂CHCO₂H, described as the "monohydrate." This diol exists in equilibrium with the dimeric hemiacetal in solution:^[4] Henry's law constant of glyoxylic acid is K_H = 1.09 × 10⁴ × exp[(40.0 × 10³/R) × (1/T − 1/298)].^[5]

2 (HO)₂CHCO₂H O[(HO)CHCO₂H]₂ + H₂O

Occurrences and Preparations

The conjugate base of gloxylic acid is known as glyoxylate and is the form that the compound exists in solution at neutral pH. Glyoxylate is an intermediate of the glyoxylate cycle, which enables organisms, such as bacteria,^[6] fungi, and plants ^[7] to convert fatty acids into carbohydrates. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.

The compound is formed by organic oxidation of glyoxal with hot nitric acid, the main side product being oxalic acid.
Ozonolysis of maleic acid is also effective.^[4]

Historically glyoxylic acid was prepared from oxalic acid electrosynthetically:^[8]^[9]

In organic synthesis, lead dioxide anodes were applied for the production of glyoxylic acid from oxalic acid in a sulfuric acid electrolyte.^[10]

Reactions and uses

Glyoxylic acid is about 10x stronger acid than acetic acid, with an acid dissociation constant of 4.7 × 10⁻⁴ (pK_a = 3.32):

(HO)₂CHCOOH (HO)₂CHCO₂⁻ + H⁺

With base, glyoxylic acid disproportionates:

2 OCHCOOH + H₂O → HOCH₂COOH + HOOC–COOH

Even though the aldehyde is a very minor component of its solutions (as with formaldehyde solutions), glyoxylic acid behaves as an aldehyde in its reactions (again like formaldehyde). For example, it gives heterocycles upon condensation with urea and 1,2-diaminobenzene.

Phenol derivatives

Its condensation with phenols is versatile. The immediate product is 4-hydroxymandelic acid. This species reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug amoxicillin. Reduction of the 4-hydroxymandelic acid gives 4-hydroxyphenylacetic acid, a precursor to the drug atenolol. Condensations with guaiacol in place of phenol provides a route to vanillin, a net formylation.^[4]^[11]^[12]

Hopkins Cole reaction

Glyoxylic acid is one of the chemicals used in the Hopkins Cole reaction, used to check for the presence of tryptophan in proteins.

Safety

The compound is not very toxic with an LD₅₀ for rats of 2500 mg/kg.

References

^ Dissociation Constants Of Organic Acids and Bases (600 compounds), http://zirchrom.com/organic.htm.
^ pKa Data Compiled by R. Williams, http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf.
^ Merck Index, 11th Edition, 4394
^ ^a ^b ^c Georges Mattioda and Yani Christidis “Glyoxylic Acid” Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_495
^ Ip, H. S. Simon; Huang, X. H. Hilda; Yu, Jian Zhen. "Effective Henry's law constants of glyoxal, glyoxylic acid, and glycolic acid". Geophysical Research Letters 36 (1). doi:10.1029/2008GL036212.
^ Holms WH (1987). "Control of flux through the citric acid cycle and the glyoxylate bypass in Escherichia coli". Biochem Soc Symp. 54: 17–31. PMID 3332993.
^ Escher CL, Widmer F (1997). "Lipid mobilization and gluconeogenesis in plants: do glyoxylate cycle enzyme activities constitute a real cycle? A hypothesis". Biol Chem. 378 (8): 803–813. PMID 9377475.
^ Tafel, Julius; and Friedrichs, Gustav (1904). "Elektrolytische Reduction von Carbonsäuren und Carbonsäureestern in schwefelsaurer Lösung". Berichte der deutschen chemischen Gesellschaft 37 (3): 3187–3191. doi:10.1002/cber.190403703116. Retrieved 19 December 2013.
^ Cohen, Julius (1920). Practical Organic Chemistry 2nd Ed. (PDF). London: Macmillan and Co. Limited. pp. 102–104.
^ François Cardarelli (2008). Materials Handbook: A Concise Desktop Reference. Springer. p. 574. ISBN 1-84628-668-9.
^ Fatiadi, Alexander; and Schaffer, Robert (1974). "An Improved Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)" (PDF). Journal of Research of the National Bureau of Standards - A. Physics and Chemistry 78A (3): 411–412. doi:10.6028/jres.078A.024. Retrieved 19 December 2013. line feed character in |title= at position 39 (help)
^ Kamlet, Jonas; and Mathieson, Olin (1953). Manufacture of vanillin and its homologues U.S. Patent 2,640,083 (PDF). U.S. Patent Office.

UpToDate Contents

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English Journal

Contribution of the tricarboxylic acid (TCA) cycle and the glyoxylate shunt in Saccharomyces cerevisiae to succinic acid production during dough fermentation.

Rezaei MN1, Aslankoohi E2, Verstrepen KJ2, Courtin CM3.
International journal of food microbiology.Int J Food Microbiol.2015 Jul 2;204:24-32. doi: 10.1016/j.ijfoodmicro.2015.03.004. Epub 2015 Mar 6.
Succinic acid produced by yeast during bread dough fermentation can significantly affect the rheological properties of the dough. By introducing mutations in the model S288C yeast strain, we show that the oxidative pathway of the TCA cycle and the glyoxylate shunt contribute significantly to succini
PMID 25828707

Plank-shaped column-forming mesogens with substituents on one side only.

Girotto E1, Ferreira M, Sarkar P, Bentaleb A, Hillard EA, Gallardo H, Durola F, Bock H.
Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2015 May 11;21(20):7603-10. doi: 10.1002/chem.201500048. Epub 2015 Mar 27.
Prolonged glyoxylation of pyrenyl-1-glyoxylic acid ethyl ester leads to a mixture of isomers with polar pyrenylene-1,8-diglyoxylic acid as the main product, whereas the centrosymmetric 1,6-isomer is obtained in good yield from the corresponding dibromopyrene. Perkin condensations followed by Pd-cata
PMID 25820523

Ach1 is involved in shuttling mitochondrial acetyl units for cytosolic C2 provision in Saccharomyces cerevisiae lacking pyruvate decarboxylase.

Chen Y1, Zhang Y1, Siewers V1, Nielsen J2.
FEMS yeast research.FEMS Yeast Res.2015 May;15(3). pii: fov015. doi: 10.1093/femsyr/fov015. Epub 2015 Apr 6.
Acetyl-coenzyme A (acetyl-CoA) is not only an essential intermediate in central carbon metabolism, but also an important precursor metabolite for native or engineered pathways that can produce many products of commercial interest such as pharmaceuticals, chemicals or biofuels. In the yeast Saccharom
PMID 25852051

Japanese Journal

1P-141 きょうかい7号バルプロ酸処理長期生存株の清酒醸造特性解析(醸造学,醸造工学,一般講演)

日本生物工学会大会講演要旨集 67, 124, 2015-09-25
NAID 110010008921

Description of the interaction between Candida albicans and macrophages by mixed and quantitative proteome analysis without isolation

AMB Express 5, 2015-07-16
NAID 120005749957

Increase in peroxisome number and the gene expression of putative glyoxysomal enzymes in Chlamydomonas cells supplemented with acetate

Journal of plant research 128(1), 177-185, 2015-01
NAID 40020349977

Related Pictures

★リンクテーブル★

リンク元	「グリオキシル酸」「glyoxalic acid」「glyoxylic acid」
拡張検索	「glyoxylate cycle」「glyoxylate pathway」

「グリオキシル酸」

Glyoxylic acid
Names
	IUPAC name oxoethanoic acid
	Other names formylformic acid; oxoethanoic acid
Identifiers
CAS Number	298-12-4
ChEBI	CHEBI:16891
ChEMBL	ChEMBL1162545
ChemSpider	740
DrugBank	DB04343
Jmol 3D model	Interactive image
KEGG	C00048
PubChem	760
	InChI InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) Key: HHLFWLYXYJOTON-UHFFFAOYSA-N ; InChI=1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) Key: HHLFWLYXYJOTON-UHFFFAOYAU ;
	SMILES C(=O)C(=O)O ;
Properties
Chemical formula	C2H2O3
Molar mass	74.04 g·mol−1
Density	1.384 g/mL
Melting point	80 °C (176 °F; 353 K)
Boiling point	111 °C (232 °F; 384 K)
Acidity (pKa)	3.18, 3.32
Related compounds
Other anions	glyoxylate
Related carboxylic acids	formic acid; acetic acid; glycolic acid; oxalic acid; propionic acid; pyruvic acid
Related compounds	acetaldehyde; glyoxal; glycolaldehyde
	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