Tartronic acid or 2-hydroxymalonic acid is an organic compound with the structural formula of HOHC(CO2H)2. This dicarboxylic acid is related to malonic acid. It is a white solid. It is produced by oxidation of glycerol:
Names | |
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Preferred IUPAC name Hydroxypropanedioic acid | |
Other names tartronic acid, 2-tartronic acid, hydroxymalonic acid, 2-hydroxymalonic acid | |
Identifiers | |
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ChemSpider | |
ECHA InfoCard | 100.001.184 |
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CompTox Dashboard (EPA) | |
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Properties | |
C3H4O5 | |
Molar mass | 120.06 g/mol |
Appearance | white solid |
Density | 1.849 g/cm3 |
Melting point | 159 °C (318 °F; 432 K) (decomposes) |
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NFPA 704 (fire diamond) | |
Related compounds | |
Related carboxylic acids | Tartaric acid Malic acid Mesoxalic acid Lactic acid 3-Hydroxypropionic acid Malonic acid Propionic acid Oxalic acid |
Related compounds | Glyceric acid Glyceraldehyde Tartonaldehyde Glycerol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
- HOCH2CH(OH)CH2OH + 2 O2 → HO2CCH(OH)CO2H + 2 H2O
Glyceric acid HOCH2CH(OH)CO2H is an intermediate.[1][2]
Its derivative, 2-methyltartronic acid, is isomalic acid.[3]
Uses
Oxidation of tartronic acid gives the ketone mesoxalic acid, the simplest oxodicarboxylic acid.[4]
References
- Hall A. N.; Kulka D.; Walker T. K. (1955). "Formation of arabinose, ribulose and tartronic acid from 2-keto-d-gluconic acid". Biochem. J. 60 (2): 271–274(4). doi:10.1042/bj0600271. PMC 1215693. PMID 14389236.
External links
- US-Patent 4319045: "Process for production of a tartronic acid solution", max 20% Tartronic acid besides other dicarbonic acids
- US-Patent 5750037: Use of tartronic acid as an oxygen scavenger
- Literature overview about synthesis