2048. Chaulmoogric Acid
Nomenclature
CAS number: 29106-32-9
(1S)-2-Cyclopentene-1-tridecanoic acid; d-13-(2-cyclopenten-1-yl)tridecanoic acid; hydnocarpylacetic acid. C18H32O2; mol wt 280.45.
C 77.09%, H 11.50%, O 11.41%.
Description and references
Isoln from chaulmoogra oil and characterization: Power, Gornall, J. Chem. Soc. 85, 838, 851 (1904); Barrowcliff, Power, ibid. 91, 557 (1907); Hashimoto, J. Am. Chem. Soc. 47, 2325 (1925); Cole, Cardoso, ibid. 61, 2349, 2351, 3442 (1939). Structure: Shriner, Adams, ibid. 47, 2727 (1925). Synthesis: Noller, Adams, ibid. 48, 1080 (1926); Perkins, Cruz, ibid. 49, 1070 (1927). Synthesis and stereochemistry: Mislow, Steinberg, ibid. 77, 3807 (1955). Activity against Mycobacterium leprae: L. Levy, Am. Rev. Respir. Dis. 111, 703 (1975). Biosynthesis: T. Kaneda, Biochem. Biophys. Res. Commun. 99, 1226 (1981).
Properties
Shiny leaflets from petr ether or alcohol. mp 68.5°. bp20 247-248°. [α]D20 +60.3° (c = 4 in chloroform). Iodine value 90.5. Freely sol in ether, chloroform, ethyl acetate; sol in other organic fat solvents.Derivative
Methyl ester.Nomenclature
CAS number: 24828-59-9
C19H34O2; mol wt 294.47.
C 77.50%, H 11.64%, O 10.87%.
Properties
Prepd by passing HCl gas into a methanol soln of the acid. Needles, mp 22°. bp20 227°. d2525 0.9119. [α]D15 +50° (c = 5 in chloroform).Derivative
Ethyl ester.Nomenclature
CAS number: 623-32-5
Chaulmestrol; Moogrol (Burroughs Wellcome). C20H36O2; mol wt 308.50.
C 77.87%, H 11.76%, O 10.37%.
Properties
Essentially a mixt of the ethyl esters of the unsaturated fatty acids (chaulmoogric and hydnocarpic) of chaulmoogra oil. Pale yellow, clear liquid; slight fruity odor; not unpleasant taste. Iodine no. 90-100. d2525 ≈0.904. [α]D25 +44.5° (chloroform). Insol in water; misc with alc, chloroform.Therapeutic Category
Ethyl ester in treatment of leprosy, sarcoidosis.