Glyceric acid
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 437056684
| Reference=Merck Index, 11th Edition, 4378.
| ImageFile=Glyceric acid.png
| ImageSize=120px
| PIN = 2,3-Dihydroxypropanoic acid
| OtherNames = Glyceric acid
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=473-81-4
| CASNo_Comment = racemate
| CASNo1 = 6000-40-4
| CASNo1_Comment = D-glyceric acid (R-enantiomer)
| CASNo2 = 28305-26-2
| CASNo2_Comment = L-glyceric acid (S-enantiomer)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 70KH64UX7G
| PubChem=752
| ChEBI = 33508
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 732
| SMILES = C(C(C(=O)O)O)O
| InChI = 1/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)
| InChIKey = RBNPOMFGQQGHHO-UHFFFAOYAE
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = RBNPOMFGQQGHHO-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula=C3H6O4
| MolarMass=106.08 g/mol
| Appearance= colorless syrup
| Density=
| MeltingPt=
| MeltingPt_notes = <25 °C
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
Glyceric acid refers to organic compounds with the formula {{chem2|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:{{cite journal |doi=10.1007/s00253-009-2124-3|title=Biotechnological production of d-glyceric acid and its application |year=2009 |last1=Habe |first1=Hiroshi |last2=Fukuoka |first2=Tokuma |last3=Kitamoto |first3=Dai |last4=Sakaki |first4=Keiji |journal=Applied Microbiology and Biotechnology |volume=84 |issue=3 |pages=445–452 |pmid=19621222 |s2cid=9144557 }}{{cite journal |doi=10.1016/S1872-2067(19)63301-2|title=Selective oxidation of glycerol in a base-free aqueous solution: A short review |year=2019 |last1=Yang |first1=Lihua |last2=Li |first2=Xuewen |last3=Chen |first3=Ping |last4=Hou |first4=Zhaoyin |journal=Chinese Journal of Catalysis |volume=40 |issue=7 |pages=1020–1034 |s2cid=196894235 |doi-access=free }}
:{{chem2|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:
:{{chem2|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.{{cite book|last1=Reece|first1=Jane B.|title=Biology|date=2009|publisher=Pearson|location=San Francisco, CA|isbn=978-0-8053-6844-4|pages=168–169|edition=8th}} 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.{{cite book|author=J. Berg, J. L. Tymoczko, L. Stryer|title=Biochemistry, 7th Edition}}
Glyceric acid occurs naturally in Populus tremula and Ardisia crenata.{{Cite web |last=PubChem |title=Glyceric acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/752 |access-date=2023-01-12 |website=pubchem.ncbi.nlm.nih.gov |language=en}}