2766. Cynarin(e)

Nomenclature

CAS number: 30964-13-7
[1R-(1α,3α,4α,5β)]-1,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-4,5-dihydroxycyclohexanecarboxylic acid; 1,3-dicaffeoylquinic acid; 1,5-dicaffeylquinic acid; 3,4-dihydroxycinnamic acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester; caffeic acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester; 1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate); quinic acid 1,5-dicaffeic ester; Cinarine; Listrocol (Farmitalia); Plemocil (Farmitalia).
C25H24O12; mol wt 516.45.
C 58.14%, H 4.68%, O 37.18%.

Description and references

Active principle of artichoke, Cynara scolymus L., Compositae: L. Panizzi, M. L. Scarpati, Gazz. Chim. Ital. 84, 792 (1954). Synthesis of originally proposed structure: L. Panizzi et al., ibid. 806; L. Panizzi et al., US 2863909; US 3100224 (1958, 1963 both to Farmitalia); Alberti et al., US 2918477 (1959). Revised structure: L. Panizzi, M. L. Scarpati, Gazz. Chim. Ital. 95, 71 (1965). NMR confirmation of structure: I. Horman et al., J. Agric. Food Chem. 32, 538 (1984). HPLC determn in pharmaceutics: A. Bettero, Boll. Chim. Farm. 120, 49 (1981). Inhibition of fatty acid mobilization: P. Dorigo, G. Fassina, Pharmacol. Res. Commun. 2, 109 (1970). Reduction of cholesterol levels in rats: J. Wojcicki, Drug Alcohol Depend. 3, 143 (1978). Clinical trial in hyperlipemic syndrome: M. Montini et al., Arzneim.-Forsch. 25, 1311 (1975).

Chemical structure

Properties

Crystals from dil acetic acid. Sweet taste. mp 225-227°. [α]D25 -59° (c = 2 in methanol). uv max (methanol): 326 nm (E1%1cm 616). Sparingly sol in cold, more in boiling water; sol in glacial acetic acid, alcohols.

Therapeutic Category

Choleretic.

Keywords

Choleretic