9068. d-Tartaric Acid

Nomenclature

CAS number: 147-71-7
(2S,3S)-2,3-Dihydroxybutanedioic acid; unusual tartaric acid; unnatural tartaric acid; l-tartaric acid; ()-tartaric acid; levotartaric acid; d-threo-2,3-dihydroxysuccinic acid.
C4H6O6; mol wt 150.09.
C 32.01%, H 4.03%, O 63.96%.

Description and references

Levorotatory tartaric acid having a dextro configuration. Although termed “unnatural,” its occurrence in nature has been demonstrated. Obtained in small amounts from racemic tartaric acid through biochemical cleavage using Penicillium notatum, Aspergillus griseus, A. niger or other microorganisms: Pasteur, Compt. Rend. 51, 298 (1860). Alternate route using salt formation with d-methylamphetamine: Walton, J. Soc. Chem. Ind. 64, 219 (1945). Monograph: K. Freudenberg, Stereochemie I, (1933), reprinted by J. W. Edwards (Ann Arbor, 1945). Crystallographic data: A. N. Winchell, The Optical Properties of Organic Compounds (Academic Press, New York, 2nd ed., 1954) p 47.

Chemical structure

Properties

Monoclinic sphenoidal prisms. d420 1.7598. mp 168-170°. [α]D20 12.0° (c = 20 in H2O). pKa1 2.93; pKa2 4.23. One gram dissolves in 0.75 ml water at room temp, in 0.5 ml boiling water, 1.7 ml methanol, 3 ml ethanol, 10.5 ml propanol, 250 ml ether. Also sol in glycerol. Insol in chloroform. Maximum soly in water at 20°: 139 g/100 ml.