Glyceric acid

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.

Glyceric acid^[1]

Names
Preferred IUPAC name 2,3-Dihydroxypropanoic acid
Other names Glyceric acid
Identifiers
CAS Number	473-81-4 racemate Y 6000-40-4 D-glyceric acid (R-enantiomer) 28305-26-2 L-glyceric acid (S-enantiomer)
3D model (JSmol)	Interactive image
ChEBI	CHEBI:33508
ChemSpider	732 N
ECHA InfoCard	100.006.795
PubChem CID	752
UNII	70KH64UX7G Y
CompTox Dashboard (EPA)	DTXSID80861979, DTXSID701016564 DTXSID30963795, DTXSID80861979, DTXSID701016564
InChI InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7) N Key: RBNPOMFGQQGHHO-UHFFFAOYSA-N 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 [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Production

Glyceric acid is usually produced by oxidation of glycerol. A typical oxidant is nitric acid, but catalytic oxidations have been developed also:^[2][3]

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.^[4] 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.^[5]

Glyceric acid occurs naturally in Populus tremula and Ardisia crenata.^[6]

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.