8479. Shellolic Acid

Nomenclature

CAS number: 4448-95-7
[3R-(3α,3aβ,4α,7β,8α,8aα)]-2,3,4,7,8,8a-Hexahydro-4-hydroxy-8-(hydroxymethyl)-8-methyl-1H-3a,7-methanoazulene-3,6-dicarboxylic acid; 10β,13-dihydroxycedr-8-ene-12,15-dioic acid.
C15H20O6; mol wt 296.32.
C 60.80%, H 6.80%, O 32.40%.

Description and references

Major component of the alicyclic fraction of shellac hydrolysate of which it usually constitutes 5-8%. Isoln: Harries, Nagel, Ber. 55, 3833 (1922); Nagel, Mertens, ibid. 70, 2173 (1937); Kirk et al., J. Am. Chem. Soc. 63, 1243 (1941). Structure studies: Carruthers et al., J. Chem. Soc. 1961, 5251; Cookson et al., Tetrahedron 18, 547, 1321 (1962); Yates, Field, ibid. 26, 3135 (1970). Stereochemistry: Yates et al., ibid. 26, 3159 (1970).

Chemical structure

Properties

Crystals, mp 204-207°.

Derivative

Dimethyl ester.

Properties

Crysts from ethyl acetate, mp 153-154.5°. uv max (ethanol): 231 nm (ε 6200).