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Sulforaphane

From Wikipedia, the free encyclopedia

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 mass177.29 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Sulforaphane (sometimessulphoraphane inBritish English) is a compound within theisothiocyanate group oforganosulfur compounds.[1] It is produced when theenzymemyrosinase transformsglucoraphanin, aglucosinolate, 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 incruciferous vegetables, such asbroccoli,Brussels sprouts, andcabbage.[1]

Sulforaphane has two possiblestereoisomers due to the presence of a stereogenic sulfur atom.[2]

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


Glucoraphanin, the glucosinolate precursor to sulforaphane

Occurrence and isolation

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Sulforaphane occurs inbroccoli sprouts, which, among cruciferous vegetables, have the highest concentration ofglucoraphanin, the precursor to sulforaphane.[1][4] It is also found incabbage,cauliflower,Brussels sprouts,bok choy,kale,collards,mustard greens, andwatercress.[1]

Research

[edit]

Although there has been somebasic research on how sulforaphane might have effectsin vivo, there is noclinical evidence that consuming cruciferous vegetables and sulforaphane affects the risk of cancer or any other disease, as of 2025.[1][5]

See also

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References

[edit]
  1. ^abcde"Isothiocyanates". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2025. Retrieved21 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. ^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):17–34.doi:10.1111/bju.13361.PMC 8631186.PMID 26898239.
Cruciferous biochemistry
Types of compounds
Glucosinolates
Isothiocyanates (ITC,mustard oils)
Bioactive metabolites
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