2323. Citramalic Acid

Nomenclature

CAS number: 2306-22-1
2-Hydroxy-2-methylbutanedioic acid; 2-methylmalic acid; 2-hydroxy-2-methylsuccinic acid; α-hydroxypyrotartaric acid.
C5H8O5; mol wt 148.11.
C 40.55%, H 5.44%, O 54.01%.

Description and references

Enzymatic synthesis: Barker, Blair, Biochem. Prep. 9, 21 (1962). Chemical synthesis: Barker, ibid. 25; J. B. Wilkes, R. G. Wall, J. Org. Chem. 45, 247 (1980). Stereoselective synthesis: E. G. J. Staring et al., Rec. Trav. Chim. 105, 374 (1986).

Chemical structure

Derivative

dl-Form.

Properties

Deliquescent monoclinic prisms from ethyl acetate + petr ether, mp 117°. Sublimes. Freely sol in water, acetone. Sol in ethyl acetate, ether. Practically insol in petr ether, benzene.

Derivative

d-Form.

Properties

Crystals, mp 112.2-112.8°. [α]D22 +23.6° (c = 3 in H2O).

Derivative

l-Form.

Properties

Crystals, mp 112-113°. [α]D20 -23.4° (c = 3 in H2O).