Chaulmoogric Acid

Title: Chaulmoogric Acid
CAS Registry Number: 29106-32-9
CAS Name: (1S)-2-Cyclopentene-1-tridecanoic acid
Additional Names: D-13-(2-cyclopenten-1-yl)tridecanoic acid; hydnocarpylacetic acid
Molecular Formula: C18H32O2
Molecular Weight: 280.45
Percent Composition: C 77.09%, H 11.50%, O 11.41%
Literature 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°. [a]D20 +60.3° (c = 4 in chloroform). Iodine value 90.5. Freely sol in ether, chloroform, ethyl acetate; sol in other organic fat solvents.
Melting point: mp 68.5°
Boiling point: bp20 247-248°
Optical Rotation: [a]D20 +60.3° (c = 4 in chloroform)
Derivative Type: Methyl ester
CAS Registry Number: 24828-59-9
Molecular Formula: C19H34O2
Molecular Weight: 294.47
Percent Composition: 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. [a]D15 +50° (c = 5 in chloroform).
Melting point: mp 22°
Boiling point: bp20 227°
Optical Rotation: [a]D15 +50° (c = 5 in chloroform)
Density: d2525 0.9119
Derivative Type: Ethyl ester
CAS Registry Number: 623-32-5
Additional Names: Chaulmestrol
Trademarks: Moogrol (Burroughs Wellcome)
Molecular Formula: C20H36O2
Molecular Weight: 308.50
Percent Composition: 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. [a]D25 +44.5° (chloroform). Insol in water; misc with alc, chloroform.
Optical Rotation: [a]D25 +44.5° (chloroform)
Density: d2525 ~0.904
Therap-Cat: Ethyl ester in treatment of leprosy, sarcoidosis.
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