Sulforaphane (sometimes sulphoraphane in
British English
British English is the set of Variety (linguistics), varieties of the English language native to the United Kingdom, especially Great Britain. More narrowly, it can refer specifically to the English language in England, or, more broadly, to ...
) is a
phytochemical within the
isothiocyanate
In organic chemistry, isothiocyanate is a functional group as found in compounds with the formula . Isothiocyanates are the more common isomers of thiocyanates, which have the formula .
Occurrence
Many isothiocyanates from plants are produce ...
group of
organosulfur compounds
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
.
It is produced when the
enzyme
An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
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
Cruciferous vegetables are vegetables of the family Brassicaceae (also called Cruciferae) with many genera, species, and cultivars being raised for food production such as cauliflower, cabbage, kale, garden cress, bok choy, broccoli, Brusse ...
, such as
broccoli
Broccoli (''Brassica oleracea'' var. ''italica'') is an edible green plant in the Brassicaceae, cabbage family (family Brassicaceae, genus ''Brassica'') whose large Pseudanthium, flowering head, plant stem, stalk and small associated leafy gre ...
,
Brussels sprouts, and
cabbage
Cabbage, comprising several cultivars of '' Brassica oleracea'', is a leafy green, red (purple), or white (pale green) biennial plant grown as an annual vegetable crop for its dense-leaved heads. It is descended from the wild cabbage ( ''B.& ...
.
[
Sulforaphane has two possible stereoisomers due to the presence of a stereogenic sulfur atom.
The R-sulforaphane ]enantiomer
In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...
occurs naturally, while the S-sulforaphane can be synthesized.
Occurrence and isolation
Sulforaphane occurs in broccoli sprouts, which, among cruciferous vegetables
Cruciferous vegetables are vegetables of the family Brassicaceae (also called Cruciferae) with many genera, species, and cultivars being raised for food production such as cauliflower, cabbage, kale, garden cress, bok choy, broccoli, Brusse ...
, have the highest concentration of glucoraphanin, the precursor to sulforaphane.[ It is also found in ]cabbage
Cabbage, comprising several cultivars of '' Brassica oleracea'', is a leafy green, red (purple), or white (pale green) biennial plant grown as an annual vegetable crop for its dense-leaved heads. It is descended from the wild cabbage ( ''B.& ...
, cauliflower
Cauliflower is one of several vegetables cultivated from the species '' Brassica oleracea'' in the genus '' Brassica'', which is in the Brassicaceae (or mustard) family. Cauliflower usually grows with one main stem that carries a large, rou ...
, Brussels sprouts, bok choy
Bok choy (American English, Canadian English, and Australian English), pak choi (British English, South African English, and Caribbean English) or pok choi is a type of Chinese cabbage ('' Brassica rapa'' subsp. ''chinensis'') cultivated as a le ...
, kale
Kale (), also called leaf cabbage, belongs to a group of cabbage (''Brassica oleracea'') cultivars primarily grown for their Leaf vegetable, edible leaves; it has also been used as an ornamental plant. Its multiple different cultivars vary quite ...
, collards, mustard greens, and watercress.[
]
Research
Although there has been basic research
Basic research, also called pure research, fundamental research, basic science, or pure science, is a type of scientific research with the aim of improving scientific theories for better understanding and prediction of natural or other phenome ...
on how sulforaphane might exert effects ''in vivo
Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, an ...
'', there is no conclusive clinical evidence that consuming cruciferous vegetables or sulforaphane supplements reduces the risk of cancer or other diseases, as of 2025.
See also
* Raphanin
References
{{Cruciferous Biochemistry
Experimental cancer drugs
Isothiocyanates
Sulfoxides
1,4-Butanediyl compounds