D-Tartaric Acid

Title: D-Tartaric Acid
CAS Registry Number: 147-71-7
CAS Name: (2S,3S)-2,3-Dihydroxybutanedioic acid
Additional Names: unusual tartaric acid; unnatural tartaric acid; l-tartaric acid; (-)-tartaric acid; levotartaric acid; D-threo-2,3-dihydroxysuccinic acid
Molecular Formula: C4H6O6
Molecular Weight: 150.09
Percent Composition: C 32.01%, H 4.03%, O 63.96%
Literature 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.
Properties: Monoclinic sphenoidal prisms. d420 1.7598. mp 168-170°. [a]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, 0.5 ml propanol, 250 ml ether. Also sol in glycerol. Insol in chloroform. Maximum soly in water at 20°: 139 g/100 ml.
Melting point: mp 168-170°
pKa: pKa1 2.93; pKa2 4.23
Optical Rotation: [a]D20 -12.0° (c = 20 in H2O)
Density: d420 1.7598
DTBP D-Threose Dulcin Duloxetine DuPHOS