9933. Vanilmandelic Acid

Nomenclature

CAS number: 55-10-7
α,4-Dihydroxy-3-methoxybenzeneacetic acid; 3-methoxy-4-hydroxymandelic acid; 4-hydroxy-3-methoxymandelic acid; VMA.
C9H10O5; mol wt 198.17.
C 54.55%, H 5.09%, O 40.37%.

Description and references

Catecholamine metabolite. Urine levels elevated in various pathologies. Misnamed vanillinemandelic acid and vanillylmandelic acid. Prepn from vanillin cyanohydrin: Gardner, Hibbert, J. Am. Chem. Soc. 66, 608 (1944). Improved procedure: Shaw et al., J. Org. Chem. 23, 30 (1958); E. F. Recondo, H. Rinderknecht, ibid. 25, 2248 (1960); I. Goodman et al., Biochem. Prep. 13, 75 (1971). Resolution: Armstrong et al., Biochim. Biophys. Acta 25, 422 (1957). Determination in urine: T. C. Stewart, J. A. Freeman, Vanilmandelic Acid & Catecholamine Determinations (Am. Soc. Clin. Pathol., Chicago, 1976) pp 1-81.

Chemical structure

Derivative

dl-Form.

Properties

Scales from ether + benzene, dec 131-133°; also reported as mp 134-135° (Goodman). uv max (0.1N HCl): 230, 279 nm (ε 6320, 2810); (0.1N NaOH): 247, 285, 345 nm (ε 6860, 3960, 630). Readily resinifies on heating or on prolonged exposure to air. Freely sol in water, acetone. Mod sol in ether, acetonitrile. Sparingly sol in benzene. Mass spectral data: T. R. Sharp, Org. Mass Spectrom. 15, 381 (1980).

Derivative

l-Form.

Properties

Crystals, dec 152°. [α]D22 +128° (c = 0.7).

Derivative

d-Form.

Properties

Crystals, dec 152°. [α]D23 131°.