Ceanothic Acid

Title: Ceanothic Acid
CAS Registry Number: 21302-79-4
CAS Name: (2a,3b)-3-Hydroxy-A(1),28-dinorlup-20(29)-ene-2,17-dicarboxylic acid
Additional Names: emmolic acid
Molecular Formula: C30H46O5
Molecular Weight: 486.68
Percent Composition: C 74.04%, H 9.53%, O 16.44%
Literature 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°. [a]D +38° (c = 1.20 in ethanol).
Melting point: mp 356-357°
Optical Rotation: [a]D +38° (c = 1.20 in ethanol)
Derivative Type: Dimethyl ester
Molecular Formula: C32H50O5
Molecular Weight: 514.74
Percent Composition: C 74.67%, H 9.79%, O 15.54%
Properties: Crystals from ether + petr ether, mp 221-223°. [a]D +41° (chloroform).
Melting point: mp 221-223°
Optical Rotation: [a]D +41° (chloroform)
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