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Tartronic acid

Summary

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:

Tartronic acid
Names
Preferred IUPAC name
Hydroxypropanedioic acid
Other names
tartronic acid,
2-tartronic acid,
hydroxymalonic acid,
2-hydroxymalonic acid
Identifiers
  • 80-69-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16513 checkY
ChemSpider
  • 44 checkY
ECHA InfoCard 100.001.184 Edit this at Wikidata
EC Number
  • 201-301-1
KEGG
  • C02287 ☒N
  • 45
UNII
  • 34T0025E0L checkY
  • DTXSID6075358 Edit this at Wikidata
  • InChI=1S/C3H4O5/c4-1(2(5)6)3(7)8/h1,4H,(H,5,6)(H,7,8) checkY
    Key: ROBFUDYVXSDBQM-UHFFFAOYSA-N checkY
  • InChI=1/C3H4O5/c4-1(2(5)6)3 (7)8/h1,4H,(H,5,6)(H,7,8)
  • InChI=1/C3H4O5/c4-1(2(5)6)3(7)8/h1,4H,(H,5,6)(H,7,8)
    Key: ROBFUDYVXSDBQM-UHFFFAOYAD
  • O=C(O)C(O)C(=O)O
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)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Related compounds
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).
☒N verify (what is checkY☒N ?)
Infobox references
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 edit

Oxidation of tartronic acid gives the ketone mesoxalic acid, the simplest oxodicarboxylic acid.[4]

References edit

  1. ^ 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.
  2. ^ 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.
  3. ^ Roelofsen, G.; Kanters, J. A.; Kroon, J.; Doesburg, H. M.; Koops, T. (1978). "Order–disorder phenomena in structures of carboxylic acids: The structures of fluoromalonic acid and hydroxymalonic acid at 20 and –150°C". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 34 (8): 2565–2570. Bibcode:1978AcCrB..34.2565R. doi:10.1107/S0567740878008596.
  4. ^ Fordham P.; Besson M.; Gallezot P. (1997). "Catalytic oxidation with air of tartronic acid to mesoxalic acid on bismuth-promoted platinum". Catal. Lett. 46 (3–4): 195–199(5). doi:10.1023/A:1019082905366. S2CID 92764231. Retrieved 2007-07-06.
  • 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 edit

  • 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