4761. Hydnocarpic Acid

Nomenclature

CAS number: 459-67-6
(1R)-2-Cyclopentene-1-undecanoic acid; 11-(2-cyclopenten-1-yl)undecanoic acid.
C16H28O2; mol wt 252.39.
C 76.14%, H 11.18%, O 12.68%.

Description and references

Component of chaulmoogra oil; naturally occurring in d-form. Isoln from seeds of Hydnocarpus wightiana Blume or H. anthelmintica Pierre, Flacourtiaceae, or from the seeds of Taraktogenos kurzii King, Bixaceae: F. B. Power, M. Barrowcliff, J. Chem. Soc. 87, 884 (1905); ibid. 91, 557 (1907). Structure: R. L. Shriner, R. Adams, J. Am. Chem. Soc. 47, 2727 (1925). Synthesis of dl-hydnocarpic acid: D. G. M. Diaper, J. C. Smith, Biochem. J. 42, 581 (1948). Toxicity data: Anderson, Int. J. Lepr. 2, 39 (1934). Antimicrobial spectrum: P. L. Jacobsen, L. Levy, Proc. West. Pharmacol. Soc. 15, 44 (1972). Mechanism of action: eidem, Antimicrob. Agents Chemother. 3, 373 (1973). Chromatographic determn in seed oils: W. W. Christie et al., Lipids 24, 116 (1989).

Chemical structure

Properties

Colorless, glistening leaflets from petr ether + ethyl acetate, mp 59-60°. [α]D +68.3° (chloroform). Sparingly sol in usual organic solvents; sol in chloroform.

Derivative

dl-Form.

Properties

Pearly plates from alcohol, ethyl actate or petr ether + ethyl acetate, mp 59-59.5°.

Derivative

Sodium salt.

Nomenclature

Sodium hydnocarpate; hydnocarpate sodium; sodium gynocardate.

Properties

Yellowish powder. Sol in water, alc. The aq soln is alkaline. MLD in rats (mg/kg): 100-125 i.v. (Anderson).

Therapeutic Category

Antibacterial (leprostatic).

Keywords

Antibacterial (Leprostatic)