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dihydroxymalonic acid : ウィキペディア英語版
dihydroxymalonic acid

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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.〔Deichsel (1864). J. Prakt. Chem. () volume 93, p. 194.〕
The compound may also be called dihydroxymesoxalic acid, dihydroxypropanedioic acid. It can be viewed as a hydrate derivative of mesoxalic acid, and indeed it is often called mesoxalic acid monohydrate and other silmilar names.〔E. T. Urbansky, W. J. Bashe (2000). Journal of Chromatography A, volume 867, pp. 143–149.〕 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.〔 It has been used in medical research as a hypoglycemic agent〔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'' ). Proceedings of the Japan Academy, volume 31, issue 8, pp.493–497.〕 and was patented in the United States in 1997 as a fast-acting antidote to cyanide poisoning.〔( Method for the treatment of cyanide poisoning )〕
==Synthesis==
Dihydroxymalonic acid can be obtained synthetically by hydrolysis of alloxan with baryta water,〔 by warming caffuric acid with lead acetate solution,〔Henry Enfield Roscoe (1888), ''A Treatise on Chemistry'', volume 3, part2 ''Organic Chemistry'', p. 161. D. Appleton and Co., New York.〕 by electrolysis of tartaric acid in alkaline solution,〔(1922), Chem. Zentralblatt III, 871〕 or from glycerin diacetate and concentrated nitric acid in the cold. The product can be obtained also by oxidation of tartronic acid
or glycerol.

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