Title: Sulforaphane
CAS Registry Number: 142825-10-3; 4478-93-7 (unspecified stereo)
CAS Name: (R)-1-Isothiocyanato-4-(methylsulfinyl)butane
Additional Names: 4-methylsulfinylbutyl isothiocyanate
Molecular Formula: C6H11NOS2
Molecular Weight: 177.29
Percent Composition: C 40.65%, H 6.25%, N 7.90%, O 9.02%, S 36.17%
Literature 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).
Properties: [a]D22 -79.3 ±1° (c = 1.223 in chloroform). [a]D25 -78.6° (c = 1.19 in chloroform). uv max (water): 238 nm (e 910 M-1cm-1); upon addition of 0.1M NaOH uv max: 226 nm (e 15300 M-1cm-1).
Optical Rotation: [a]D22 -79.3 ±1° (c = 1.223 in chloroform); [a]D25 -78.6° (c = 1.19 in chloroform)
Absorption maximum: uv max (water): 238 nm (e 910 M-1cm-1); uv max: 226 nm (e 15300 M-1cm-1) |