9071. meso-Tartaric Acid

Nomenclature

CAS number: 147-73-9
(2R,3S)-rel-2,3-Dihydroxybutanedioic acid; mesotartaric acid; internally compensated tartaric acid; unresolvable tartaric acid; Antiweinsure (German).
C4H6O6; mol wt 150.09.
C 32.01%, H 4.03%, O 63.96%.

Description and references

Prepd by boiling l-tartaric acid with alkali; as byproduct of racemization: Winther, Z. Phys. Chem. 56, 507 (1906); Holleman, Org. Synth. coll. vol. I (2nd ed., 1941) p 497; Milas, US 2414385 (1947). Microbial prepn: Martin, Foster, J. Bacteriol. 70, 405 (1955); Foster, US 2947665 (1960). Explanation of optical inactivity: Noller, Science 102, 508 (1945); C. R. Noller, Chemistry of Organic Compounds (Philadelphia, 2nd ed., 1957) p 339.

Chemical structure

Derivative

Monohydrate.

Properties

Rectangular plates, d420 1.666 (also reported as 1.737). mp 140° (also reported as 159-160°). pKa1 3.11; pKa2 4.80. Maximum soly in water at 20°: 125 g/100 ml.