142825-10-3CS(=O)CCCCN=C=SSUVMJBTUFCVSAD-UHFFFAOYSA-NSulforaphane is an isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen. It has a role as an antioxidant, an antineoplastic agent, an EC 3.5.1.98 (histone deacetylase) inhibitor and a plant metabolite. It is a sulfoxide and an isothiocyanate.
142825-10-3、4478-93-7DTXSID8036732CHEMBL48802CHEBI:47807Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
DescriptionSulforaphane is a compound within the isothiocyanate group of organosulfur compounds and mainly found in cruciferous vegetables. It is produced when the enzyme myrosinase transforms glucoraphanin,a prodrug or storage form of SFN, into SFN upon damage to the plant (such as from chewing),which allows the two compounds to mix and react. Glucoraphanin is one of a few molecules known as isothiocyanates, existing alongside Sinigrin (metabolized into allylisothiocyanate).
UsesPotent, selective inducer of phase II detoxification enzymes with anticarcinogenic properties. Occurs naturally in broccoli. It was found to inhibit chemically induced mammary tumor formation in rats. Antitumor agentLNCaP prostate cancer cells were treated with DL-Sulforaphane to study the effect on androgen receptor. Effects on malathion toxicity was studied in rats by treating them with DL-Sulforaphane.Nrf2 activation of the antioxidant response element (ARE) is central to cytoprotective gene expression against oxidative and/or electrophilic stress.Unless activated by inflammatory, environmental, or oxidative stressors, Nrf2 is sequestered in the cytoplasm by its repressor, Keap1.Because of its protective capabilities, small molecules that activate Nrf2 signaling are being examined as potential anti-cancer or anti-inflammatory agents.Sulforaphane is an isothiocyanate derived from cruciferous vegetables, including broccoli, that potently induces chemopreventative enzymes via Keap1-Nrf2 signaling and ARE-driven gene expression.At 15 μM, sulforaphane inhibits class I and II HDAC activity and suppresses tumor growth by inducing cell cycle arrest and apoptosis selectively in various cancerous prostate epithelial cells without affecting normal cells.Differential effects of sulforaphane on histone deacetylases, cell cycle arrest and apoptosis in normal prostate cells versus hyperplastic and cancerous prostate cells
General DescriptionAn isothiocyanate isolated from broccoli that acts as a potent inducer of phase II detoxifying enzymes in mouse tissues and murine hepatoma cells in culture. It has been shown to be an effective agent in prevention of chemically-induced mammary tumors in rats. It also inhibits the phase I cytochrome P450 isoenzymes 2E1 and IA2 which have been associated with the activation of carcinogens. The induction of phase II enzymes is mediated by mitogen-activated protein kinase (MAPK) pathway.
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PreparationCurrently, there are three main methods for the artificial synthesis of DL-Sulforaphane: 1. Chemical synthesis; 2. Enzymatic method; 3. A combination of chemical and enzymatic methods. 1. Chemical synthesis: In 2003, a research group led by Desai et al. synthesized DL-Sulforaphane in five steps using isotope labeling, with a yield of ~10%. 2. Enzymatic method: The DL-Sulforaphane precursor, glucoraphane glycoside, is extracted from cruciferous vegetables and then hydrolyzed to prepare DL-Sulforaphane. 3. Combination of chemical and enzymatic methods: A method combining chemical synthesis and enzymatic extraction involves extracting glucosyltriernate from arugula seeds, using glucosyltriernate as a raw material, and then selectively oxidizing it to prepare glucoraphane glycoside, followed by hydrolysis to obtain DL-Sulforaphane. This process holds promise for industrialization.
DefinitionChEBI: Sulforaphane is an isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen. It has a role as an antineoplastic agent, a plant metabolite, an antioxidant and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a sulfoxide and an isothiocyanate.