Sulforaphane
Names
Preferred IUPAC name
1-Isothiocyanato-4-(methanesulfinyl)butane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3 ☒N
    Key: SUVMJBTUFCVSAD-UHFFFAOYSA-N ☒N
  • 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).
☒N verify (what is checkY☒N ?)

Sulforaphane (sometimes sulphoraphane in British English) is a compound 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]

The R-sulforaphane enantiomer occurs naturally, while the S-sulforaphane can be synthesized.[3]


Glucoraphanin, the glucosinolate precursor to sulforaphane

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.[1]

Research

Although there has been some basic research on how sulforaphane might have effects in vivo, there is no clinical evidence that consuming cruciferous vegetables and sulforaphane affects the risk of cancer or any other disease, as of 2017.[1][5]

See also

References

  1. ^ a b c d e "Isothiocyanates". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 1 April 2017. Retrieved 14 July 2022.
  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. ^ Zhang Y, Lu Q, Li N, Xu M, Miyamoto T, Liu J (March 2022). "Sulforaphane suppresses metastasis of triple-negative breast cancer cells by targeting the RAF/MEK/ERK pathway". npj Breast Cancer. 8 (1): 40. doi:10.1038/s41523-022-00402-4. PMC 8948359. PMID 35332167.
  4. ^ 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.
  5. ^ van Die MD, Bone KM, Emery J, Williams SG, Pirotta MV, Paller CJ (April 2016). "Phytotherapeutic interventions in the management of biochemically recurrent prostate cancer: a systematic review of randomised trials". BJU International. 117 Suppl 4 (Suppl 4): 17–34. doi:10.1111/bju.13361. PMC 8631186. PMID 26898239.
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