1909. Ceanothic Acid
Nomenclature
CAS number: 21302-79-4
(2α,3β)-3-Hydroxy-A(1),28-dinorlup-20(29)-ene-2,17-dicarboxylic
acid; emmolic acid. C30H46O5; mol wt 486.68.
C 74.04%, H 9.53%, O 16.44%.
Description and references
From Ceanothus americanus L., Rhamnaceae (New Jersey tea). Isoln: Julian et al., J. Am. Chem. Soc. 60, 77 (1938). Identity of ceanothic acid and emmolic acid: Mechoulam, Chem. Ind. (London) 1961, 1835. Structure: de Mayo, Starratt, Tetrahedron Lett. 1961, 259; Mechoulam, J. Org. Chem. 27, 4070 (1962). Stereochemistry: de Mayo, Starratt, Can. J. Chem. 40, 788 (1962). Revised stereochemistry: Eade et al., Aust. J. Chem. 24, 621 (1971).
Properties
Crystals from methanol + ether, mp 356-357°. [α]D +38° (c = 1.20 in ethanol).Derivative
Dimethyl ester.C32H50O5; mol wt 514.74.
C 74.67%, H 9.79%, O 15.54%.