869. Atranorin

Nomenclature

CAS number: 479-20-9
3-Formyl-2,4-dihydroxy-6-methylbenzoic acid 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester; atranoric acid.
C19H18O8; mol wt 374.34.
C 60.96%, H 4.85%, O 34.19%.

Description and references

From a number of lichens. Belongs to the group of lichen acids. Isoln: Paterno, Ogliarori, Gazz. Chim. Ital. 1877, 189; Hesse, Ber. 30, 357, 1983 (1897); St. Pfau, Helv. Chim. Acta 9, 650 (1926). Synthesis: Neelakantan et al., Tetrahedron Lett. 1962, 287. TLC analysis: R. Klee, L. Steubing, J. Chromatogr. 129, 478 (1976); J. L. Ramaut et al., ibid. 155, 450 (1978).

Chemical structure

Properties

Bitter crystals or cryst powder from chloroform, mp 195°. Practically insol in water; slightly sol in alc; sol in boiling benzene or in chloroform; also sol in alkalies giving a yellow soln.