Sulforaphane

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Sulforaphane
Sulforaphane.svg
Sulforaphane-3D-balls.png
Sulforaphane-3D-vdW.png
Names
Preferred IUPAC name
1-Isothiocyanato-4-(methanesulfinyl)butane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3 X mark.svgN
    Key: SUVMJBTUFCVSAD-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
    Key: SUVMJBTUFCVSAD-UHFFFAOYAY
  • CS(=O)CCCCN=C=S
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Sulforaphane (sometimes sulphoraphane in British English) is a phytochemical within the isothiocyanate group of organosulfur compounds. [1] 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. [1] Sulforaphane has two possible stereoisomers due to the presence of a stereogenic sulfur atom. [2]

Occurrence and isolation

Glucoraphanin, the glucosinolate precursor to sulforaphane Glucoraphanin.png
Glucoraphanin, the glucosinolate precursor to sulforaphane

Sulforaphane occurs in broccoli sprouts, which, among cruciferous vegetables, have the highest concentration of glucoraphanin, the precursor to sulforaphane. [1] [3] It is also found in cabbage, cauliflower, Brussels sprouts, bok choy, kale, collards, mustard greens, and watercress. [1]

Research

Clinical evidence is limited and inconclusive regarding the effects of sulforaphane on cancer risk. [1]

See also

References

  1. 1 2 3 4 5 "Isothiocyanates". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2025. Retrieved 21 January 2025.
  2. ↑ Janczewski Ł (March 2022). "Sulforaphane and Its Bifunctional Analogs: Synthesis and Biological Activity". Molecules. 27 (5): 1750. doi: 10.3390/molecules27051750 . PMC   8911885 . PMID   35268851.
  3. ↑ Houghton CA, Fassett RG, Coombes JS (November 2013). "Sulforaphane: translational research from laboratory bench to clinic". Nutrition Reviews. 71 (11): 709–726. doi: 10.1111/nure.12060 . PMID   24147970.
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