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Glyceric acid

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Glyceric acid
Names
Preferred IUPAC name 2,3-Dihydroxypropanoic acid
Other names Glyceric acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.795 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)Key: RBNPOMFGQQGHHO-UHFFFAOYSA-N
  • InChI=1/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)Key: RBNPOMFGQQGHHO-UHFFFAOYAE
SMILES
  • C(C(C(=O)O)O)O
Properties
Chemical formula C3H6O4
Molar mass 106.08 g/mol
Appearance colorless syrup
Melting point <25 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Glyceric acid refers to organic compounds with the formula HOCH2CH(OH)CO2H. It occurs naturally and is classified as three-carbon sugar acid. It is chiral. Salts and esters of glyceric acid are known as glycerates.

Production

Glyceric acid is usually produced by oxidation of glycerol. A typical oxidant is nitric acid, but catalytic oxidations have been developed also:

HOCH2CH(OH)CH2OH + O2 → HOCH2CH(OH)CO2H + H2O

As glycerol is prochiral, the oxidation of the two terminal alcohol groups gives distinct enantiomers of glyceric acid. Oxidation of both primary alcohols gives tartronic acid:

HOCH2CH(OH)CH2OH + 2 O2 → HO2CCH(OH)CO2H + 2 H2O

Biochemistry

Several phosphate derivatives of glyceric acid, including 2-phosphoglyceric acid, 3-phosphoglyceric acid, 2,3-bisphosphoglyceric acid, and 1,3-bisphosphoglyceric acid, are intermediates in glycolysis. 3-Phosphoglyceric acid is an intermediate in the biosynthesis of the amino acid serine, which in turn can be used in the synthesis of glycine and cysteine.

Glyceric acid occurs naturally in Populus tremula and Ardisia crenata.

References

  1. Merck Index, 11th Edition, 4378.
  2. Habe, Hiroshi; Fukuoka, Tokuma; Kitamoto, Dai; Sakaki, Keiji (2009). "Biotechnological production of d-glyceric acid and its application". Applied Microbiology and Biotechnology. 84 (3): 445–452. doi:10.1007/s00253-009-2124-3. PMID 19621222. S2CID 9144557.
  3. Yang, Lihua; Li, Xuewen; Chen, Ping; Hou, Zhaoyin (2019). "Selective oxidation of glycerol in a base-free aqueous solution: A short review". Chinese Journal of Catalysis. 40 (7): 1020–1034. doi:10.1016/S1872-2067(19)63301-2. S2CID 196894235.
  4. Reece, Jane B. (2009). Biology (8th ed.). San Francisco, CA: Pearson. pp. 168–169. ISBN 978-0-8053-6844-4.
  5. J. Berg, J. L. Tymoczko, L. Stryer. Biochemistry, 7th Edition.{{cite book}}: CS1 maint: multiple names: authors list (link)
  6. PubChem. "Glyceric acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-01-12.
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