8962. Sulforaphane
Nomenclature
CAS number: 142825-10-3;
4478-93-7
(unspecified stereo)
(R)-1-Isothiocyanato-4-(methylsulfinyl)butane; 4-methylsulfinylbutyl isothiocyanate. C6H11NOS2; mol wt 177.29.
C 40.65%, H 6.25%, N 7.90%, O 9.02%, S 36.17%.
Description and references
Potent, selective inducer of phase II detoxification enzymes with anticarcinogenic properties. Occurs naturally in broccoli. Prepn: H. Schmid, P. Karrer, Helv. Chim. Acta 31, 1497 (1948). Absolute configuration: K. Mislow et al., J. Am. Chem. Soc. 87, 665 (1965). Isoln from SAGA broccoli and enzyme inducing activities: Y. Zhang et al., Proc. Natl. Acad. Sci. USA 89, 2399 (1992). Asymmetric synthesis: J. K. Whitesell, M.-S. Wong, J. Org. Chem. 59, 597 (1994). In vivo antitumor activity: Y. Zhang et al., Proc. Natl. Acad. Sci. USA 91, 3147 (1994). Mechanism of action study: M. C. Myzak et al., Cancer Res. 64, 5767 (2004). Review of antioxidant activitiy: J. W. Fahey, P. Talalay, Food Chem. Toxicol. 37, 973-979 (1999).
