Tartronic acid

Tartronic acid
Names
	Preferred IUPAC name Hydroxypropanedioic acid
	Other names tartronic acid,; 2-tartronic acid,; hydroxymalonic acid,; 2-hydroxymalonic acid
Identifiers
CAS Number	80-69-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16513 ;
ChemSpider	44 ;
ECHA InfoCard	100.001.184
EC Number	201-301-1;
KEGG	C02287 ;
PubChem CID	45;
UNII	34T0025E0L ;
CompTox Dashboard (EPA)	DTXSID6075358 ;
	InChI InChI=1S/C3H4O5/c4-1(2(5)6)3(7)8/h1,4H,(H,5,6)(H,7,8) Key: ROBFUDYVXSDBQM-UHFFFAOYSA-N ; 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;
	SMILES O=C(O)C(O)C(=O)O;
Properties
Chemical formula	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)	2 0 0
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). verify (what is ?) Infobox references

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:

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

^ 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.
^ 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.
^ 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

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

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[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.

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Names

Preferred IUPAC name Hydroxypropanedioic acid
Other names tartronic acid, 2-tartronic acid, hydroxymalonic acid, 2-hydroxymalonic acid
Identifiers
CAS Number	80-69-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16513^Y
ChemSpider	44^Y
ECHA InfoCard	100.001.184
EC Number	201-301-1
KEGG	C02287^N
PubChem CID	45
UNII	34T0025E0L^Y
CompTox Dashboard (EPA)	DTXSID6075358
InChI InChI=1S/C3H4O5/c4-1(2(5)6)3(7)8/h1,4H,(H,5,6)(H,7,8)^Y Key: ROBFUDYVXSDBQM-UHFFFAOYSA-N^Y 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
SMILES O=C(O)C(O)C(=O)O
Properties
Chemical formula	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)	2 0 0
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). N verify (what is ^YN ?) Infobox references