Allyl Isothiocyanate
Structural Formula Vector Image
Title: Allyl Isothiocyanate
CAS Registry Number: 57-06-7
CAS Name: 3-Isothiocyanato-1-propene
Additional Names: isothiocyanic acid allyl ester; allyl isosulfocyanate; "mustard oil"; allyl mustard oil
Molecular Formula: C4H5NS
Molecular Weight: 99.15
Percent Composition: C 48.45%, H 5.08%, N 14.13%, S 32.34%
Literature References: Principal constituent of volatile oil of mustard. Occurs in seeds as the glucoside, sinigrin, q.v. Isolated from Brassica nigra (L.) Koch, Cruciferae (black mustard seed), or prepd from allyl iodide and potassium thiocyanate: Dulière, J. Pharm. Belg. 2, 981 (1920), C.A. 15, 5714 (1921). Description: E. Guenther, D. Althausen, The Essential Oils vol. II (Van Nostrand, New York, 1949) pp. 734-7. Review of isolation: E. Guenther, ibid. vol VI, pp. 55-60 (1952); and synthesis: G. M. Dyson, Perfum. Essent. Oil Rec. 20, 42 (1929). Evaluation in relieving muscle pain: J. G. Macarthur, S. Alstead, Lancet 2, 1060 (1953). Toxicity study: P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964). HPLC determn in brown mustard: K. Kanemaru et al., J. Jpn. Soc. Food Sci. Technol. 37, 565 (1990).
Properties: Colorless or pale yellow, very refractive liquid; very pungent, irritating odor; acrid taste. d415 1.024. bp 152°. nD25 1.5248. Sparingly sol in water; misc with alcohol and most organic solvents. One ml dissolves in 8 ml 70% alcohol. LD50 orally in rats: 339 mg/kg (Jenner).
Boiling point: bp 152°
Index of refraction: nD25 1.5248
Density: d415 1.024
Toxicity data: LD50 orally in rats: 339 mg/kg (Jenner)
Use: Manuf flavors; war gas.
Therap-Cat: Counterirritant.
Therap-Cat-Vet: Counterirritant.

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