Undecylenic Acid
Title: Undecylenic Acid
CAS Registry Number: 112-38-9
CAS Name: 10-Undecenoic acid
Additional Names: 10-hendecenoic acid; 9-undecylenic acid
Trademarks: Fungoid Solution (Pedinol); Mycodécyl Solution (Doms-Adrian)
Molecular Formula: C11H20O2
Molecular Weight: 184.28
Percent Composition: C 71.69%, H 10.94%, O 17.36%
Line Formula: CH2=CH(CH2)8CO2H
Literature 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).
Melting point: mp 24.5°
Boiling point: bp760 275° (dec); bp182 232-235°; bp130 230-235°; bp100 213.5°; bp90 198-200°; bp15 168.3°; bp1.0 131°
Index of refraction: nD25 1.4486
Density: d424 (vac) 0.9072; d2525 0.9102; d4545 0.8993; d479.9 (vac) 0.8653
Toxicity data: LD50 in mice (g/kg): 8.15 orally; 0.960 i.p. (Newell)
 
Derivative Type: Zinc salt
CAS Registry Number: 557-08-4
Additional Names: Zinc undecylenate
Molecular Formula: C22H38O4Zn
Molecular Weight: 431.94
Percent Composition: 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.
Melting point: mp 115-116°
 
Derivative Type: Mixture with zinc salt
Trademarks: Cruex (Novartis); Desenex (Novartis); Fungex (Streuli); Turexan Crème (Turimed)
 
Derivative Type: Methyl ester
Molecular Formula: C12H22O2
Molecular Weight: 198.30
Percent Composition: 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.
Melting point: mp -27.5°
Boiling point: bp760 248°; bp10 124°
Index of refraction: nD20 1.43928; nD25 1.43727
Density: d415 0.889
 
Therap-Cat: Antifungal (topical).
Therap-Cat-Vet: Antifungal (topical).
Keywords: Antifungal (Synthetic).

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