Dihydroxymalonic acid

Dihydroxymalonic acid[1]
Names
Preferred IUPAC name
Dihydroxypropanedioic acid
Other names
Mesoxalic acid monohydrate
Oxomalonic acid monohydrate
Ketomalonic acid monohydrate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.372 Edit this at Wikidata
UNII
  • InChI=1S/C3H4O6/c4-1(5)3(8,9)2(6)7/h8-9H,(H,4,5)(H,6,7) checkY
    Key: VUCKYGJSXHHQOJ-UHFFFAOYSA-N checkY
  • InChI=1/C3H4O6/c4-1(5)3(8,9)2(6)7/h8-9H,(H,4,5)(H,6,7)
    Key: VUCKYGJSXHHQOJ-UHFFFAOYAF
  • C(=O)(C(C(=O)O)(O)O)O
  • O=C(O)C(O)(O)C(=O)O
Properties
C3H4O6
Molar mass 136.059 g·mol−1
Melting point 119 to 120 °C (246 to 248 °F; 392 to 393 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Dihydroxymalonic acid is an organic compound with formula C3H4O6 or HO-(C=O)-C(OH)2-(C=O)-OH, found in some plants such as alfalfa and in beet molasses.[2]

The compound is also called dihydroxymesoxalic acid and dihydroxypropanedioic acid. It can be viewed as a hydrate derivative of mesoxalic acid, and is often called mesoxalic acid monohydrate and similar names.[3] This compound is unusual in containing stable geminal hydroxy groups.

Dihydroxymalonic acid is a water-soluble white solid. It crystallizes in deliquescent prisms that melt between 113 °C and 121 °C without loss of water.[4] It has been used in medical research as a hypoglycemic agent[5] and was patented in the United States in 1997 as a fast-acting antidote to cyanide poisoning.[6]

  1. ^ Merck Index, 12th Edition, 5971.
  2. ^ Deichsel, Theodor (1864). "Ueber die Mesoxalsäure". J. Prakt. Chem. (in German). 93 (1): 193–208. doi:10.1002/prac.18640930139.
  3. ^ E. T. Urbansky, W. J. Bashe (2000). Journal of Chromatography A, volume 867, pp. 143–149.
  4. ^ Cite error: The named reference roscoe was invoked but never defined (see the help page).
  5. ^ Yoshito KOBAYASHI, Shigeru OHASHI, Shinzaburo TANAKA and Akitoshi SHIOYA (1955), Hypoglycemic Action of Sodium Mesoxalate with Special Reference to Hyperfunction of Pituitary-Adrenal Cortical System in Dogs Exposed to Cold[permanent dead link]. Proceedings of the Japan Academy, volume 31, issue 8, pp.493–497.
  6. ^ "Method for the treatment of cyanide poisoning". Archived from the original on 2017-05-11. Retrieved 2009-11-13.