Sulforaphane
Chemical compound
From Wikipedia, the free encyclopedia
Sulforaphane (sometimes sulphoraphane in British English) is a phytochemical within the isothiocyanate group of organosulfur compounds.[1] Although sulforaphane research on cancer has been ongoing for many years, there is no good clinical evidence to indicate consuming sulforaphane-rich vegetables or dietary supplements provides any effect.[1][2]
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| Names | |
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| Preferred IUPAC name
1-Isothiocyanato-4-(methanesulfinyl)butane | |
| Identifiers | |
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CompTox Dashboard (EPA) |
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| Properties | |
| C6H11NOS2 | |
| Molar mass | 177.29 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis
It is produced when the enzyme myrosinase transforms glucoraphanin, a glucosinolate, into sulforaphane upon damage to the plant (such as from chewing or chopping during food preparation), which allows the two compounds to mix and react.
Sulforaphane is present in cruciferous vegetables, such as broccoli, Brussels sprouts, and cabbage. Sulforaphane has two possible stereoisomers due to the presence of a stereogenic sulfur atom.[3]
Occurrence and isolation
Sulforaphane occurs in broccoli sprouts, which, among cruciferous vegetables, have the highest concentration of glucoraphanin, the precursor to sulforaphane.[1][4] It is also found in cabbage, cauliflower, Brussels sprouts, bok choy, kale, collards, mustard greens, and watercress.
Under conditions where broccoli is cooked, sulforaphane converts to the thiourea ((CH3SO(CH2)4NH)2CS) as well as some 1,2,4-trithiolane.[5]
Research
Although substantial animal research on the possible anti-cancer effects of sulforaphane has been reported, there is no substantial clinical research to indicate consuming foods rich in sulforaphane provides any benefit against cancer.[1]