Title: Quinovic Acid
CAS Registry Number: 465-74-7
CAS Name: (3b)-3-Hydroxyurs-12-ene-27,28-dioic acid
Synonyms: quinovaic acid; chinovic acid; chinova acid
Molecular Formula: C30H46O5
Molecular Weight: 486.68
Percent Composition: C 74.04%, H 9.53%, O 16.44%
Literature 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. [a]D20 +99° (c = 2.48 in pyridine). Practically insol in water and other solvents except pyridine.
Optical Rotation: [a]D20 +99° (c = 2.48 in pyridine)
Derivative Type: O-Acetylquinovic acid
Molecular Formula: C32H48O6
Molecular Weight: 528.72
Percent Composition: C 72.69%, H 9.15%, O 18.16%
Properties: Needles from dilute acetone, mp 282-284°.
Melting point: mp 282-284°
Derivative Type: Dimethyl ester
Molecular Formula: C32H50O5
Molecular Weight: 514.74
Percent Composition: C 74.67%, H 9.79%, O 15.54%
Properties: Needles from dil acetone, mp 175°. [a]D19 +117.4° (c = 2.2 in CHCl3). Sol in organic solvents.
Melting point: mp 175°
Optical Rotation: [a]D19 +117.4° (c = 2.2 in CHCl3)
