9848. Undecylenic Acid
Nomenclature
CAS number: 112-38-9
10-Undecenoic acid; 10-hendecenoic acid; 9-undecylenic acid; Fungoid Solution (Pedinol); Mycodécyl Solution (Doms-Adrian). C11H20O2; mol wt 184.28.
C 71.69%, H 10.94%, O 17.36%.
Description and references
Prepn from castor oil: Krafft, Ber. 10, 2035 (1877); Perkins, Cruz, J. Am. Chem. Soc. 49, 1073 (1927); G. Das et al., J. Am. Oil Chem. Soc. 66, 938 (1989). Toxicology: G. W. Newell et al., J. Invest. Dermatol. 13, 145 (1949). Clinical trials: A. L. Shapiro, S. Rothman, Arch. Dermatol. Syphilol. 52, 166 (1945), republ. in Arch. Dermatol. 119, 345 (1983); J. H. Chretien et al., Int. J. Dermatol. 19, 51 (1980). Historical review: J. W. Landau, Arch. Dermatol. 119, 351-353 (1983).
Properties
Liquid or crystals. Odor suggestive of perspiration. d424 (vac) 0.9072; d2525 0.9102; d4545 0.8993; d479.9 (vac) 0.8653. mp 24.5°; bp760 275° (dec); bp182 232-235°; bp130 230-235°; bp100 213.5°; bp90 198-200°; bp15 168.3°; bp1.0 131°. nD25 1.4486. Neutralization value 304.5; iodine value 137.8. Insol in water. Sol in alcohol, chloroform, ether. LD50 in mice (g/kg): 8.15 orally; 0.960 i.p. (Newell).Derivative
Zinc salt.Nomenclature
CAS number: 557-08-4
Zinc undecylenate. C22H38O4Zn; mol wt 431.94.
C 61.17%, H 8.87%, O 14.82%, Zn 15.14%.
Properties
Amorphous white powder, mp 115-116°. Resembles zinc stearate in appearance and physical properties. Can be prepd by dissolving zinc oxide in dil undecylenic acid and concentrating the solution.Derivative
Mixture with zinc salt.Nomenclature
Cruex (Novartis); Desenex (Novartis); Fungex (Streuli); Turexan Crème (Turimed).Derivative
Methyl ester.Nomenclature
CAS number: 111-81-9
C12H22O2; mol wt 198.30.
C 72.68%, H 11.18%, O 16.14%.
Properties
Liq; d415 0.889; bp760 248°; bp10 124°; mp 27.5°; nD20 1.43928; nD25 1.43727. Sol in alcohol, chloroform, ether, petr ether, oils.Therapeutic Category
Antifungal (topical).
Therapeutic Category (Veterinary)
Antifungal (topical).Keywords
Antifungal (Synthetic)