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).
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Sulforaphane (sometimes sulphoraphane in British English) is a phytochemical [1] within the isothiocyanate group of organosulfur compounds. [2] 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. [2]

Sulforaphane has two possible stereoisomers due to the presence of a stereogenic sulfur atom. [3]

The R-sulforaphane enantiomer occurs naturally, while the S-sulforaphane can be synthesized. [4]

Glucoraphanin.png
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. [2] [5] It is also found in cabbage, cauliflower, Brussels sprouts, bok choy, kale, collards, mustard greens, and watercress. [2]

Research

Although there has been basic research on how sulforaphane might exert effects in vivo , there is no conclusive clinical evidence that consuming cruciferous vegetables or sulforaphane supplements reduces the risk of cancer or other diseases, as of 2025. [2] [6]

See also

References

  1. ↑ The Impact of Sulforaphane on Sex-Specific Conditions and Hormone Balance: A Comprehensive Review. By: Fahey, Jed W., Raphaely, Mirran, Applied Sciences (2076-3417), 20763417, Jan2025, Vol. 15, Issue 2
  2. 1 2 3 4 5 "Isothiocyanates". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2025. Retrieved 21 January 2025.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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): 17–34. doi: 10.1111/bju.13361 . PMC   8631186 . PMID   26898239.
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