7537. Plicatic Acid

Nomenclature

CAS number: 16462-65-0
(1S,2S,3R)-1-(3,4-Dihydroxy-5-methoxyphenyl)-1,2,3,4-tetrahydro-2,3,7-trihydroxy-3-(hydroxymethyl)-6-methoxy-2-naphthalenecarboxylic acid.
C20H22O10; mol wt 422.38.
C 56.87%, H 5.25%, O 37.88%.

Description and references

Coloring constituent and agent associated with western red cedar asthma. Low-molecular weight lignan which occurs as the (-)-form. Isolation from the heartwood of western red cedar, Thuja plicata Donn: J. A. F. Gardner et al., Can. J. Chem. 37, 1703 (1959). Structure determn: idem et al., ibid. 44, 52 (1966). Absolute configuration: R. J. Swan et al., ibid. 45, 319 (1967). Chromatographic analysis: B. F. MacDonald, E. P. Swan, J. Chromatogr. 51, 553 (1970). Identification as coloring material: Y. Kai, E. P. Swan, Mokuzai Gakkaishi 36, 218 (1990). Role in asthma: M. Chan-Yeung et al., Am. Rev. Respir. Dis. 108, 1094 (1973); eidem, J. Allergy Clin. Immunol. 79, 792 (1987). Mechanism of action study: M. Chan-Yeung, Am. J. Ind. Med. 25, 13 (1994).

Chemical structure

Properties

Light tan powder. [α]D21 -9.99° (water). uv max (water): 281 nm (log ε 3.58). pKa: 3.0. Very sol in water; sol in absolute acetone and ethanol; very slightly sol in ethyl acetate and ether.