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Glyoxylic acid information


Glyoxylic acid
Skeletal formula of glyoxylic acid
Space-filling model of glyoxylic acid
Names
Preferred IUPAC name
Oxoacetic acid[1]
Systematic IUPAC name
Oxoethanoic acid
Other names
Glyoxylic acid[1]
2-Oxoacetic acid
Formylformic acid
Identifiers
CAS Number
  • 298-12-4 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
741891
ChEBI
  • CHEBI:16891 checkY
ChEMBL
  • ChEMBL1162545 checkY
ChemSpider
  • 740 checkY
DrugBank
  • DB04343 checkY
ECHA InfoCard 100.005.508 Edit this at Wikidata
EC Number
  • 206-058-5
Gmelin Reference
25752
KEGG
  • C00048 checkY
PubChem CID
  • 760
UNII
  • JQ39C92HH6 checkY
CompTox Dashboard (EPA)
  • DTXSID5021594 Edit this at Wikidata
InChI
  • InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) checkY
    Key: HHLFWLYXYJOTON-UHFFFAOYSA-N checkY
  • 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 74.035 g·mol−1
Density 1.384 g/mL
Melting point 80 °C (176 °F; 353 K)[4]
Boiling point 111 °C (232 °F; 384 K)
Acidity (pKa) 3.18,[2] 3.32 [3]
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).
checkY verify (what is checkY☒N ?)
Infobox references

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.

  1. ^ a b "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 748. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Dissociation Constants Of Organic Acids and Bases (600 compounds), http://zirchrom.com/organic.htm.
  3. ^ pKa Data Compiled by R. Williams, "Archived copy" (PDF). Archived from the original (PDF) on 2010-06-02. Retrieved 2010-06-02.{{cite web}}: CS1 maint: archived copy as title (link).
  4. ^ Merck Index, 11th Edition, 4394

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Glyoxylic acid

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industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid may be used to form acid addition salts with drugs to make them more...

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guaiacol and glyoxylic acid. Beginning in 2000, Rhodia began marketing biosynthetic vanillin prepared by the action of microorganisms on ferulic acid extracted...

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Adamkiewicz reaction

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presence of the amino acid tryptophan in proteins. When concentrated sulfuric acid is combined with a solution of protein and glyoxylic acid, a red/purple colour...

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Ethylene dione

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carbon monoxide. It can also be thought of as the dehydrated form of glyoxylic acid (H(C=O)COOH), or a ketone of ethenone H2C=C=O. The existence of ethylenedione...

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Lead dioxide

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production of glyoxylic acid from oxalic acid in a sulfuric acid electrolyte. The most important use of lead dioxide is as the cathode of lead acid batteries...

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Glyoxal

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p. 40 : "This residue consisted almost entirely of the aldehyde of glyoxylic acid ; I proposed to call it Glyoxal, C2H4O3." H. Debus (1857) "On glyoxal...

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Vanillylmandelic acid

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Specifically the reaction entails the condensation of guaiacol and glyoxylic acid in an ice cold, aqueous solution with sodium hydroxide. VMA is found...

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Ethylvanillin

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to give guaethol (1). This ether condenses with glyoxylic acid to give the corresponding mandelic acid derivative (2), which by oxidation (3) and decarboxylation...

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Glyoxylate reductase

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oxidoreductase. Other names in common use include NADH-glyoxylate reductase, glyoxylic acid reductase, and NADH-dependent glyoxylate reductase. The crystal structure...

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Semialdehyde

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glyoxylic acid, semialdehydes often exist as hydrates (geminal diols) HO2C(CH2)nCH(OH)2. Some of semialdehydes and their parent dicarboxylic acids are...

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Pyruvic acid

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involving glyoxylate or dicarboxylates. Glyoxylate is the conjugate base of glyoxylic acid, and within a buffered environment of known pH such as the cell cytoplasm...

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Vitamin B12 total synthesis

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it displays instead its propionic acid function at ring D as carboxylate (as shown in fig. 1), or carboxylic acid (with two cyanide ligands at cobalt)...

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Guaiacol

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condensation reaction of glyoxylic acid with guaiacol to give mandelic acid, which is oxidized to produce phenylglyoxylic acid. This acid undergoes a decarboxylation...

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Plastic degradation by marine bacteria

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ethylene glycol are the acetaldehyde/ethanol pathway and the glyoxylic acid pathway. The glyoxylic acid pathway is commonly studied in the Pseudomonas genus as...

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Piperonal

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accomplished through a condensation reaction with glyoxylic acid followed by cleaving the resulting α-hydroxy acid with an oxidizing agent. Synthesis from catechol...

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Electrosynthesis

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carboxylic acid (oxalic acid) to an aldehyde (glyoxylic acid, shows as the rare aldehyde form) in a divided cell: Originally phenylpropanoic acid could be...

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Ethylene glycol poisoning

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cytotoxic effect of glycolic acid. The glycolic acid is then metabolized to glyoxylic acid and finally to oxalic acid. Oxalic acid binds with calcium to form...

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C2H2O3

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u) may refer to: Formic anhydride, or methanoic anhydride Glyoxylic acid, or oxoacetic acid This set index page lists chemical structure articles associated...

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compound with the formula CH3C(O)CHO. It is a reduced derivative of pyruvic acid. It is a reactive compound that is implicated in the biology of diabetes...

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Petasis reaction

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4-dioxane), but the resultant carboxylic acid is obtained in reasonable yield. Usage of α-ketoacids instead of glyoxylic acid does not diminish yields. 1,3,5-trioxygenated...

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