Glyceric acid

Glyceric acid

File:Glyceric acid.png
Names
Preferred IUPAC name 2,3-Dihydroxypropanoic acid
Other names Glyceric acid
Identifiers
CAS Number	473-81-4 racemate checkY 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
E number
PubChem CID	752
UNII	70KH64UX7G checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
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 checkY☒N ?) Infobox references

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.