Names | |
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Preferred IUPAC name 1-Isothiocyanato-4-(methanesulfinyl)butane | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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). |
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 |
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]
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] [ needs update ]
Cabbage, comprising several cultivars of Brassica oleracea, is a leafy green, red (purple), or white biennial plant grown as an annual vegetable crop for its dense-leaved heads. It is descended from the wild cabbage, and belongs to the "cole crops" or brassicas, meaning it is closely related to broccoli and cauliflower ; Brussels sprouts ; and Savoy cabbage.
Broccoli is an edible green plant in the cabbage family whose large flowering head, stalk and small associated leaves are eaten as a vegetable. Broccoli is classified in the Italica cultivar group of the species Brassica oleracea. Broccoli has large flower heads, or florets, usually dark green, arranged in a tree-like structure branching out from a thick stalk, which is usually light green. The mass of flower heads is surrounded by leaves. Broccoli resembles cauliflower, which is a different but closely related cultivar group of the same Brassica species.
Brassica is a genus of plants in the cabbage and mustard family (Brassicaceae). The members of the genus are informally known as cruciferous vegetables, cabbages, mustard plants, or simply brassicas. Crops from this genus are sometimes called cole crops—derived from the Latin caulis, denoting the stem or stalk of a plant.
In organic chemistry, isothiocyanate is a functional group as found in compounds with the formula R−N=C=S. Isothiocyanates are the more common isomers of thiocyanates, which have the formula R−S−C≡N.
The Brussels sprout is a member of the Gemmifera cultivar group of cabbages, grown for its edible buds.
Kale, also called leaf cabbage, belongs to a group of cabbage cultivars primarily grown for their edible leaves. It has also been used as an ornamental plant.
Brassica oleracea is a plant species from the family Brassicaceae that includes many common cultivars used as vegetables, such as cabbage, broccoli, cauliflower, kale, Brussels sprouts, collard greens, Savoy cabbage, kohlrabi, and gai lan. The uncultivated form of the species, wild cabbage, is native to southwest Europe.
3,3′-Diindolylmethane (DIM) is a compound derived from the digestion of indole-3-carbinol, found in cruciferous vegetables, such as broccoli, Brussels sprouts, cabbage and kale. It and its parent compound – indole-3-carbinol – are under laboratory research to determine their possible biological properties, particularly in anti-cancer mechanisms. DIM is sold as a dietary supplement.
Glucoraphanin is a glucosinolate found in broccoli, mustard and other cruciferous vegetables.
Glucosinolates are natural components of many pungent plants such as mustard, cabbage, and horseradish. The pungency of those plants is due to mustard oils produced from glucosinolates when the plant material is chewed, cut, or otherwise damaged. These natural chemicals most likely contribute to plant defence against pests and diseases, and impart a characteristic bitter flavor property to cruciferous vegetables.
Cruciferous vegetables are vegetables of the family Brassicaceae with many genera, species, and cultivars being raised for food production such as cauliflower, cabbage, kale, garden cress, bok choy, broccoli, Brussels sprouts, mustard plant and similar green leaf vegetables. The family takes its alternative name from the shape of their flowers, whose four petals resemble a cross.
Indole-3-carbinol (I3C, C9H9NO) is produced by the breakdown of the glucosinolate glucobrassicin, which can be found at relatively high levels in cruciferous vegetables such as broccoli, cabbage, cauliflower, brussels sprouts, collard greens and kale. It is also available in dietary supplements. Indole-3-carbinol is the subject of on-going biomedical research into its possible anticarcinogenic, antioxidant, and anti-atherogenic effects. Research on indole-3-carbinol has been conducted primarily using laboratory animals and cultured cells. Limited and inconclusive human studies have been reported. A recent review of the biomedical research literature found that "evidence of an inverse association between cruciferous vegetable intake and breast or prostate cancer in humans is limited and inconsistent" and "larger randomized controlled trials are needed" to determine if supplemental indole-3-carbinol has health benefits.
Glucobrassicin is a type of glucosinolate that can be found in almost all cruciferous plants, such as cabbages, broccoli, mustards, and woad. As for other glucosinolates, degradation by the enzyme myrosinase is expected to produce an isothiocyanate, indol-3-ylmethylisothiocyanate. However, this specific isothiocyanate is expected to be highly unstable, and has indeed never been detected. The observed hydrolysis products when isolated glucobrassicin is degraded by myrosinase are indole-3-carbinol and thiocyanate ion, which are envisioned to result from a rapid reaction of the unstable isothiocyanate with water. However, a large number of other reaction products are known, and indole-3-carbinol is not the dominant degradation product when glucosinolate degradation takes place in crushed plant tissue or in intact plants.
The diamondback moth, sometimes called the cabbage moth, is a moth species of the family Plutellidae and genus Plutella. The small, grayish-brown moth sometimes has a cream-colored band that forms a diamond along its back. The species may have originated in Europe, South Africa, or the Mediterranean region, but it has now spread worldwide.
Myrosinase is a family of enzymes involved in plant defense against herbivores, specifically the mustard oil bomb. The three-dimensional structure has been elucidated and is available in the PDB.
Broccoli sprouts are three- to four-day-old broccoli plants that look like alfalfa sprouts, but taste like radishes.
Goitrin is an organosulfur compound classified as a derivative of oxazolidine and as a cyclic thiocarbamate. It reduces the production of thyroid hormones such as thyroxine. It is found in cruciferous vegetables such as cabbage, brussels sprouts and rapeseed oil, and is formed by the hydrolysis of a glucosinolate: progoitrin or 2-hydroxy-3-butenyl glucosinolate. The unstable isothiocyanate derived from the latter glucosinolate spontaneously cyclizes to goitrin, because the hydroxy group is situated in proximity to the isothiocyanate group. Hence, the oxygen in the molecule stems from the hydroxy group of the original unstable isothiocyanate. Plants containing this specific glucosinolate have goitrogenic potential due to the goitrin and thiocyanate they contain. However, they do not seem to alter thyroid function in humans at realistic amounts in the diet.
Paul Talalay was the John Jacob Abel Distinguished Service Professor of Pharmacology and director of the Laboratory for Molecular Sciences at the Johns Hopkins School of Medicine in Baltimore. He was the founder of the Brassica Chemoprotection Laboratory for the study of edible plants that induce protective enzyme activity in the body and may help prevent the development of cancer.
Erucin is a dietary isothiocyanate present in cruciferous vegetables that is considered a potential cancer chemopreventive nutraceutical.