7226. Phenethyl Isothiocyanate

Nomenclature

CAS number: 2257-09-2
(2-Isothiocyanatoethyl)benzene; 2-phenylethyl isothiocyanate; PEITC.
C9H9NS; mol wt 163.24.
C 66.22%, H 5.56%, N 8.58%, S 19.64%.

Description and references

Chemopreventive agent found in cruciferous vegetables; produced by hydrolysis of gluconasturtiin. Prepn: J. v. Braun, H. Deutsch, Ber. 45, 2188 (1912); E. Schmidt et al., Ann. 612, 11 (1958); and isoln from turnips: E. P. Lichtenstein et al., J. Agric. Food Chem. 10, 30 (1962). Isoln from cabbage and watercress seeds: N. Kaoulla et al., Phytochemistry 19, 1053 (1980). LC/MS determn in plasma and urine: Y. Ji, M. E. Morris, Anal. Biochem. 323, 39 (2003). Chemopreventive studies in animal models: G. D. Stoner, Curr. Top. Plant Physiol. 15, 78 (1995); A. Nishikawa et al., Curr. Cancer Drug Targets 4, 373 (2004). Mechanistic studies of anticancer activity and induction of apoptosis: Y.-R. Chen et al., J. Biol. Chem. 277, 39334 (2002); R. Hu et al., Carcinogenesis 24, 1361 (2003); D. Xiao et al., Clin. Cancer Res. 11, 2670 (2005).

Chemical structure

Properties

Colorless to pale yellow liquid, bp11 139-140°. bp1.4-1.5 102-103°. nD20 1.5904. d420 1.0942. LD50 in mice (mg/kg): 700 orally; 150 s.c.; 50 i.v. (Lichtenstein).

Use

Flavor ingredient; provides the hot or burning sensation in horseradish.