Glyceric acid
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| Names | |
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| Preferred IUPAC name
2,3-Dihydroxypropanoic acid | |
| Other names
Glyceric acid
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| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.006.795 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| 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).
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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
[edit]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
[edit]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
[edit]- ^ Merck Index, 11th Edition, 4378.
- ^ 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.
- ^ 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.
- ^ Reece, Jane B. (2009). Biology (8th ed.). San Francisco, CA: Pearson. pp. 168–169. ISBN 978-0-8053-6844-4.
- ^ J. Berg, J. L. Tymoczko, L. Stryer. Biochemistry, 7th Edition.
((cite book)): CS1 maint: multiple names: authors list (link) - ^ PubChem. "Glyceric acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-01-12.
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