8075. Quinovic Acid
Nomenclature
CAS number: 465-74-7
(3β)-3-Hydroxyurs-12-ene-27,28-dioic acid; quinovaic acid; chinovic acid; chinova acid. C30H46O5; mol wt 486.68.
C 74.04%, H 9.53%, O 16.44%.
Description and references
Isoln from cinchona bark as the glycoside quinovin: Hlasiwetz, Ann. 79, 129 (1851); 111, 182 (1859); Votocek, Rác, Collect. Czech. Chem. Commun. 1, 234 (1929); Tschesche et al., Ann. 667, 151 (1963); from Zygophyllum coccineum L., Zygophyllaceae: Soliman, J. Chem. Soc. 1939, 1760; from bark of Mitragyna inermis Kuntze and leaves of M. ciliata Aubrev & Pellegr. and M. rubrostipulacea Havil., Rubiaceae: Badger et al., ibid. 1950, 867. Structure: Brossi et al., Helv. Chim. Acta 34, 244 (1951); Barton, de Mayo, J. Chem. Soc. 1953, 3111. Review: J. Simonsen, W. C. J. Ross, The Terpenes vol. 5 (University Press, Cambridge, 1957) pp 75-113.
Properties
Prisms from dil pyridine, decomp 297°. Very bitter taste. [α]D20 +99° (c = 2.48 in pyridine). Practically insol in water and other solvents except pyridine.Derivative
O-Acetylquinovic acid.C32H48O6; mol wt 528.72.
C 72.69%, H 9.15%, O 18.16%.
Properties
Needles from dilute acetone, mp 282-284°.Derivative
Dimethyl ester.C32H50O5; mol wt 514.74.
C 74.67%, H 9.79%, O 15.54%.