EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes

butane, 1-isothiocyanato-4-(methylsulfinyl)-

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CAS Number: 4478-93-7Picture of molecule3D/inchi
Nikkaji Web:J13.479A
Beilstein Number:1723237
XlogP3-AA:1.40 (est)
Molecular Weight:177.28987000
Formula:C6 H11 N O S2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:cosmetic agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 368.00 to 369.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.000027 mmHg @ 25.00 °C. (est)
Flash Point: 350.00 °F. TCC ( 176.50 °C. ) (est)
logP (o/w): 0.407 (est)
Soluble in:
 water, 1.382e+004 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: bleaching agents
skin protecting agents
Alfa Biotechnology
For experimental / research use only.
Sulforafan 98%
BOC Sciences
For experimental / research use only.
Odor: characteristic
Use: Sulforaphaneis a naturally-occurring phytochemical belonging to the class of isothiocyanates. As the aglycone metabolite of glucosinolate glucoraphanin (sulforaphane glucosinolate), sulforaphane acts as an antioxidant and potent stimulator of endogenous
Santa Cruz Biotechnology
For experimental / research use only.
D,L-Sulforaphane ≥97%
Sigma-Aldrich: Sigma
For experimental / research use only.
DL-Sulforaphane ≥90% (HPLC), synthetic, liquid
Safety Information:
Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
cosmetic agents
Recommendation for sulforafan usage levels up to:
 not for fragrance use.
Recommendation for sulforafan flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5350
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5350
Pubchem (sid):135065750
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):HMDB05792
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 broccoli asparagus broccoli plant
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 brussel sprout plant
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 cabbage leaf
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 cardaria draba
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 butane, 1-isothiocyanato-4-(methylsulfinyl)-
4-(methyl thio) butyl isothiocyanate
4-(methylsulfinyl)butyl isothiocyanate
4-methylsulfinylbutyl isothiocyanate
4-methylsulphinylbutyl glucosinolate
4-(methylthio)butyl isothiocyanate
1-isothiocyanato-4-(methyl sulfinyl) butane
4-isothiocyanatobutyl methyl sulfoxide


PubMed:Nrf2 status affects tumor growth, HDAC3 gene promoter associations, and the response to sulforaphane in the colon.
PubMed:Glucosinolates Are Mainly Absorbed Intact in Germfree and Human Microbiota-Associated Mice.
PubMed:Development of a liquid chromatography-electrospray ionization-tandem mass spectrometry method for the simultaneous analysis of intact glucosinolates and isothiocyanates in Brassicaceae seeds and functional foods.
PubMed:Associations between cruciferous vegetable intake and selected biomarkers among women scheduled for breast biopsies.
PubMed:Sulforaphane inhibits damage-induced poly (ADP-ribosyl)ation via direct interaction of its cellular metabolites with PARP-1.
PubMed:Sulforaphane induces apoptosis in adipocytes via Akt/p70s6k1/Bad inhibition and ERK activation.
PubMed:Identification of dialkyl diacetylene diols with potent cancer chemopreventive activity.
PubMed:Effect of Se treatment on glucosinolate metabolism and health-promoting compounds in the broccoli sprouts of three cultivars.
PubMed:Correction: Sulforaphane protected the injury of human vascular endothelial cell induced by LPC through up-regulating endogenous antioxidants and phase II enzymes.
PubMed:Analysis of autophagic flux in response to sulforaphane in metastatic prostate cancer cells.
PubMed:Sulforaphane protected the injury of human vascular endothelial cell induced by LPC through up-regulating endogenous antioxidants and phase II enzymes.
PubMed:Antioxidant and anticancer activities of broccoli by-products from different cultivars and maturity stages at harvest.
PubMed:Diet rich in high glucoraphanin broccoli reduces plasma LDL cholesterol: Evidence from randomised controlled trials.
PubMed:Sulforaphane protects against acetaminophen-induced hepatotoxicity.
PubMed:Development and validation of a LC-MS/MS method to determine sulforaphane in honey.
PubMed:Myrosinase-treated glucoerucin is a potent inducer of the Nrf2 target gene heme oxygenase 1--studies in cultured HT-29 cells and mice.
PubMed:The Epigenetic Impact of Cruciferous Vegetables on Cancer Prevention.
PubMed:Effect of Sulforaphane on NOD2 via NF-κB: implications for Crohn's disease.
PubMed:Bioavailability and biotransformation of sulforaphane and erucin metabolites in different biological matrices determined by LC-MS-MS.
PubMed:Direct and indirect antioxidant activity of polyphenol- and isothiocyanate-enriched fractions from Moringa oleifera.
PubMed:[Protective effects of sulforaphane on the oxidative damage of kidney mitochondria complex in obese rats induced by high-fat diet].
PubMed:Absorption and chemopreventive targets of sulforaphane in humans following consumption of broccoli sprouts or a myrosinase-treated broccoli sprout extract.
PubMed:The intake of broccoli sprouts modulates the inflammatory and vascular prostanoids but not the oxidative stress-related isoprostanes in healthy humans.
PubMed:Effect of light on quality and bioactive compounds in postharvest broccoli florets.
PubMed:Dietary broccoli mildly improves neuroinflammation in aged mice but does not reduce lipopolysaccharide-induced sickness behavior.
PubMed:Berteroin present in cruciferous vegetables exerts potent anti-inflammatory properties in murine macrophages and mouse skin.
PubMed:Sulforaphane suppresses cardiac hypertrophy by inhibiting GATA4/GATA6 expression and MAPK signaling pathways.
PubMed:Suppression of LPS-induced transcription and cytokine secretion by the dietary isothiocyanate sulforaphane.
PubMed:Sulforaphane inhibits TNF-α-induced adhesion molecule expression through the Rho A/ROCK/NF-κB signaling pathway.
PubMed:Neuroprotective effects of sulforaphane on cholinergic neurons in mice with Alzheimer's disease-like lesions.
PubMed:Phytochemical modulators of mitochondria: the search for chemopreventive agents and supportive therapeutics.
PubMed:Exogenous methyl jasmonate treatment increases glucosinolate biosynthesis and quinone reductase activity in kale leaf tissue.
PubMed:Antioxidant and Anti-inflammatory Activities of Broccoli Florets in LPS-stimulated RAW 264.7 Cells.
PubMed:Total myrosinase activity estimates in brassica vegetable produce.
PubMed:Sulforaphane and prostate cancer interception.
PubMed:Camelina sativa defatted seed meal contains both alkyl sulfinyl glucosinolates and quercetin that synergize bioactivity.
PubMed:Transcriptome analysis reveals a dynamic and differential transcriptional response to sulforaphane in normal and prostate cancer cells and suggests a role for Sp1 in chemoprevention.
PubMed:Sulforaphane ameliorates neurobehavioral deficits and protects the brain from amyloid β deposits and peroxidation in mice with Alzheimer-like lesions.
PubMed:Sulforaphane induces apoptosis in T24 human urinary bladder cancer cells through a reactive oxygen species-mediated mitochondrial pathway: the involvement of endoplasmic reticulum stress and the Nrf2 signaling pathway.
PubMed:Enhancement of broccoli indole glucosinolates by methyl jasmonate treatment and effects on prostate carcinogenesis.
PubMed:Isothiocyanate metabolism, distribution, and interconversion in mice following consumption of thermally processed broccoli sprouts or purified sulforaphane.
PubMed:Sulforaphane attenuates homocysteine-induced endoplasmic reticulum stress through Nrf-2-driven enzymes in immortalized human hepatocytes.
PubMed:Hydroxybenzoic acid isomers and the cardiovascular system.
PubMed:Beyond androgen deprivation: ancillary integrative strategies for targeting the androgen receptor addiction of prostate cancer.
PubMed:From the Table to the Bedside: Can Food-Derived Sulforaphane be used as a Novel Agent to Treat Leukemia?
PubMed:Sulforaphane alleviates scopolamine-induced memory impairment in mice.
PubMed:Inhibitory effect of Raphanobrassica on Helicobacter pylori-induced gastritis in Mongolian gerbils.
PubMed:Sulforaphane inhibits phorbol ester-stimulated IKK-NF-κB signaling and COX-2 expression in human mammary epithelial cells by targeting NF-κB activating kinase and ERK.
PubMed:Off-target effects of sulforaphane include the derepression of long terminal repeats through histone acetylation events.
PubMed:Glucosinolates from pak choi and broccoli induce enzymes and inhibit inflammation and colon cancer differently.
PubMed:In vivo formation and bioavailability of isothiocyanates from glucosinolates in broccoli as affected by processing conditions.
PubMed:Anti-Inflammatory and Anti-Superbacterial Properties of Sulforaphane from Shepherd's Purse.
PubMed:Study on degradation kinetics of sulforaphane in broccoli extract.
PubMed:Molecular targets of isothiocyanates in cancer: recent advances.
PubMed:Simultaneous determination of sulphoraphane and sulphoraphane nitrile in Brassica vegetables using ultra-performance liquid chromatography with tandem mass spectrometry.
PubMed:Sulforaphane attenuates obesity by inhibiting adipogenesis and activating the AMPK pathway in obese mice.
PubMed:Transcriptomic responses of cancerous and noncancerous human colon cells to sulforaphane and selenium.
PubMed:Nrf2 regulates the expression of the peptide transporter PEPT1 in the human colon carcinoma cell line Caco-2.
PubMed:The broccoli-born isothiocyanate sulforaphane impairs nucleotide excision repair: XPA as one potential target.
PubMed:Optimization of methyl jasmonate application to broccoli florets to enhance health-promoting phytochemical content.
PubMed:Effect of NaCl stress on health-promoting compounds and antioxidant activity in the sprouts of three broccoli cultivars.
PubMed:Sulforaphane induces reactive oxygen species-mediated mitotic arrest and subsequent apoptosis in human bladder cancer 5637 cells.
PubMed:Sulforaphane-rich broccoli sprout extract attenuates nasal allergic response to diesel exhaust particles.
PubMed:DSS-induced acute colitis in C57BL/6 mice is mitigated by sulforaphane pre-treatment.
PubMed:The metabolism of methylsulfinylalkyl- and methylthioalkyl-glucosinolates by a selection of human gut bacteria.
PubMed:Astaxanthin and omega-3 fatty acids individually and in combination protect against oxidative stress via the Nrf2-ARE pathway.
PubMed:Optimization of a blanching step to maximize sulforaphane synthesis in broccoli florets.
PubMed:A new ultra-rapid UHPLC/MS/MS method for assessing glucoraphanin and sulforaphane bioavailability in human urine.
PubMed:Nutraceuticals for prostate cancer chemoprevention: from molecular mechanisms to clinical application.
PubMed:Influence of seasonal variation and methyl jasmonate mediated induction of glucosinolate biosynthesis on quinone reductase activity in broccoli florets.
PubMed:Supercritical CO2 extraction, chemical characterisation and antioxidant potential of Brassica oleracea var capitata against HO·, O2(·-) and ROO·.
PubMed:Sulforaphane is superior to glucoraphanin in modulating carcinogen-metabolising enzymes in Hep G2 cells.
PubMed:Kinetics of sulforaphane in mice after consumption of sulforaphane-enriched broccoli sprout preparation.
PubMed:Modifying the processing and handling of frozen broccoli for increased sulforaphane formation.
PubMed:Effects of bioactive-rich extracts of pomegranate, persimmon, nettle, dill, kale and Sideritis and isolated bioactives on arachidonic acid induced markers of platelet activation and aggregation.
PubMed:Response surface optimization and identification of isothiocyanates produced from broccoli sprouts.
PubMed:Isothiocyanates protect against oxidized LDL-induced endothelial dysfunction by upregulating Nrf2-dependent antioxidation and suppressing NFκB activation.
PubMed:Chronic sulforaphane oral treatment accentuates blood glucose impairment and may affect GLUT3 expression in the cerebral cortex and hypothalamus of rats fed with a highly palatable diet.
PubMed:An approach to the phytochemical profiling of rocket [Eruca sativa (Mill.) Thell].
PubMed:Lack of effect of bioactive-rich extracts of pomegranate, persimmon, nettle, dill, kale and Sideritis and isolated bioactives on platelet function.
PubMed:Potential efficacy of broccoli sprouts as a unique supplement for management of type 2 diabetes and its complications.
PubMed:Molecular mechanisms of chemopreventive phytochemicals against gastroenterological cancer development.
PubMed:Lactic acid bacteria convert glucosinolates to nitriles efficiently yet differently from enterobacteriaceae.
PubMed:The potential to intensify sulforaphane formation in cooked broccoli (Brassica oleracea var. italica) using mustard seeds (Sinapis alba).
PubMed:Synthesis and Nrf2-inducing activity of the isothiocyanates iberverin, iberin and cheirolin.
PubMed:Dietary regulation of histone acetylases and deacetylases for the prevention of metabolic diseases.
PubMed:Longevity in the red flour beetle Tribolium castaneum is enhanced by broccoli and depends on nrf-2, jnk-1 and foxo-1 homologous genes.
PubMed:Sulforaphane and related mustard oils in focus of cancer prevention and therapy.
PubMed:Arsenic-mediated activation of the Nrf2-Keap1 antioxidant pathway.
PubMed:An overview of health-promoting compounds of broccoli (Brassica oleracea var. italica) and the effect of processing.
PubMed:Epithelial-mesenchymal transition, a novel target of sulforaphane via COX-2/MMP2, 9/Snail, ZEB1 and miR-200c/ZEB1 pathways in human bladder cancer cells.
PubMed:Isothiocyanate concentrations and interconversion of sulforaphane to erucin in human subjects after consumption of commercial frozen broccoli compared to fresh broccoli.
PubMed:Inhibition of bladder cancer by broccoli isothiocyanates sulforaphane and erucin: characterization, metabolism, and interconversion.
PubMed:Interactions of sulforaphane and dimethyl sulfoxide with methyl methanesulfonate, urethane, 4-nitroquinoline-1-oxide and hydrogen peroxide in the Drosophila melanogaster wing spot test.
PubMed:Enhanced in vitro biological activity of synthetic 2-(2-pyridyl) ethyl isothiocyanate compared to natural 4-(methylsulfinyl) butyl isothiocyanate.
PubMed:Maintaining quality and bioactive compounds of broccoli by combined treatment with 1-methylcyclopropene and 6-benzylaminopurine.
PubMed:Enhanced Nrf2 activity worsens insulin resistance, impairs lipid accumulation in adipose tissue, and increases hepatic steatosis in leptin-deficient mice.
PubMed:Metabolic effects of sulforaphane oral treatment in streptozotocin-diabetic rats.
PubMed:Isothiocyanates ameliorate the symptom of heart dysfunction and mortality in a murine AIDS model by inhibiting apoptosis in the left ventricle.
PubMed:TrxR1 and GPx2 are potently induced by isothiocyanates and selenium, and mutually cooperate to protect Caco-2 cells against free radical-mediated cell death.
PubMed:Characterization of products from the reaction of glucosinolate-derived isothiocyanates with cysteine and lysine derivatives formed in either model systems or broccoli sprouts.
PubMed:Synergy between sulforaphane and selenium in the up-regulation of thioredoxin reductase and protection against hydrogen peroxide-induced cell death in human hepatocytes.
PubMed:Keap1-nrf2 signaling: a target for cancer prevention by sulforaphane.
PubMed:Sulforaphane potentiates the efficacy of imatinib against chronic leukemia cancer stem cells through enhanced abrogation of Wnt/β-catenin function.
PubMed:Cancer stem cells: potential target for bioactive food components.
PubMed:Structural influence of isothiocyanates on expression of cytochrome P450, phase II enzymes, and activation of Nrf2 in primary rat hepatocytes.
PubMed:Characterization of the temporal induction of hepatic xenobiotic-metabolizing enzymes by glucosinolates and isothiocyanates: requirement for at least a 6 h exposure to elicit complete induction profile.
PubMed:Effect of broccoli sprouts on insulin resistance in type 2 diabetic patients: a randomized double-blind clinical trial.
PubMed:Impact of thermal processing on sulforaphane yield from broccoli ( Brassica oleracea L. ssp. italica).
PubMed:Cruciferous vegetable phytochemical sulforaphane affects phase II enzyme expression and activity in rat cardiomyocytes through modulation of Akt signaling pathway.
PubMed:In vivo biological activity of rocket extracts (Eruca vesicaria subsp. sativa (Miller) Thell) and sulforaphane.
PubMed:Synergistic anti-inflammatory effects of nobiletin and sulforaphane in lipopolysaccharide-stimulated RAW 264.7 cells.
PubMed:Dietary factors and epigenetic regulation for prostate cancer prevention.
PubMed:Bioactive food components prevent carcinogenic stress via Nrf2 activation in BRCA1 deficient breast epithelial cells.
PubMed:6-Benzylaminopurine delays senescence and enhances health-promoting compounds of harvested broccoli.
PubMed:Physiological and biochemical metabolism of germinating broccoli seeds and sprouts.
PubMed:Allyl isothiocyanate as a potential inducer of paraoxonase-1--studies in cultured hepatocytes and in mice.
PubMed:Nutritional influences on epigenetics and age-related disease.
PubMed:Reactive oxygen species and PI3K/Akt signaling play key roles in the induction of Nrf2-driven heme oxygenase-1 expression in sulforaphane-treated human mesothelioma MSTO-211H cells.
PubMed:Epigenetic events associated with breast cancer and their prevention by dietary components targeting the epigenome.
PubMed:Glucoraphanin does not reduce plasma homocysteine in rats with sufficient Se supply via the induction of liver ARE-regulated glutathione biosynthesis enzymes.
PubMed:Comparison of isothiocyanate metabolite levels and histone deacetylase activity in human subjects consuming broccoli sprouts or broccoli supplement.
PubMed:Enhancing sulforaphane absorption and excretion in healthy men through the combined consumption of fresh broccoli sprouts and a glucoraphanin-rich powder.
PubMed:Health benefits and possible risks of broccoli - an overview.
PubMed:Glucoraphanin hydrolysis by microbiota in the rat cecum results in sulforaphane absorption.
PubMed:Cyanidin does not affect sulforaphane-mediated Nrf2 induction in cultured human keratinocytes.
PubMed:LC-MS/MS quantification of sulforaphane and indole-3-carbinol metabolites in human plasma and urine after dietary intake of selenium-fortified broccoli.
PubMed:Anti-inflammatory potential of allyl-isothiocyanate--role of Nrf2, NF-(κ) B and microRNA-155.
PubMed:Of cabbages and kings.
PubMed:3,3'-Diindolylmethane but not indole-3-carbinol activates Nrf2 and induces Nrf2 target gene expression in cultured murine fibroblasts.
PubMed:Phenethyl isothiocyanate sensitizes human cervical cancer cells to apoptosis induced by cisplatin.
PubMed:Food: The omnivore's labyrinth.
PubMed:Differential effects of sulforaphane on histone deacetylases, cell cycle arrest and apoptosis in normal prostate cells versus hyperplastic and cancerous prostate cells.
PubMed:Extraction and identification of isothiocyanates from broccolini seeds.
PubMed:Exposure to isothiocyanates suppresses urinary mutagenicity in rats treated with heterocyclic amine IQ: lack of association with CYP1 activity.
PubMed:Broccoli ( Brassica oleracea var. italica) sprouts and extracts rich in glucosinolates and isothiocyanates affect cholesterol metabolism and genes involved in lipid homeostasis in hamsters.
PubMed:Sulforaphane absorption and excretion following ingestion of a semi-purified broccoli powder rich in glucoraphanin and broccoli sprouts in healthy men.
PubMed:Allyl-, butyl- and phenylethyl-isothiocyanate activate Nrf2 in cultured fibroblasts.
PubMed:Sulphoraphane inhibited the expressions of intercellular adhesion molecule-1 and vascular cell adhesion molecule-1 through MyD88-dependent toll-like receptor-4 pathway in cultured endothelial cells.
PubMed:Sulforaphane modulates the expression of Cyp6a2 and Cyp6g1 in larvae of the ST and HB crosses of the Drosophila wing spot test and is genotoxic in the ST cross.
PubMed:Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals.
PubMed:Induction of detoxification enzymes by feeding unblanched Brussels sprouts containing active myrosinase to mice for 2 wk.
PubMed:Cancer prevention with natural compounds.
PubMed:Dietary polyphenol quercetin targets pancreatic cancer stem cells.
PubMed:The dietary isothiocyanate sulforaphane modulates gene expression and alternative gene splicing in a PTEN null preclinical murine model of prostate cancer.
PubMed:Isothiocyanate sulforaphane inhibits protooncogenic ornithine decarboxylase activity in colorectal cancer cells via induction of the TGF-β/Smad signaling pathway.
PubMed:Analysis and anti-Helicobacter activity of sulforaphane and related compounds present in broccoli ( Brassica oleracea L.) sprouts.
PubMed:Protective effect of sulforaphane on human vascular endothelial cells against lipopolysaccharide-induced inflammatory damage.
PubMed:p38 MAPK plays a distinct role in sulforaphane-induced up-regulation of ARE-dependent enzymes and down-regulation of COX-2 in human bladder cancer cells.
PubMed:Sulforaphane protects cortical neurons against 5-S-cysteinyl-dopamine-induced toxicity through the activation of ERK1/2, Nrf-2 and the upregulation of detoxification enzymes.
PubMed:Mouse models for unraveling the importance of diet in colon cancer prevention.
PubMed:The impact of loss of myrosinase on the bioactivity of broccoli products in F344 rats.
PubMed:Effect of sulforaphane on glutathione-adduct formation and on glutathione_S_transferase-dependent detoxification of acrylamide in Caco-2 cells.
PubMed:Combination treatment with resveratrol and sulforaphane induces apoptosis in human U251 glioma cells.
PubMed:Protective effect of sulforaphane on indomethacin-induced cytotoxicity via heme oxygenase-1 expression in human intestinal Int 407 cells.
PubMed:Sulforaphane suppresses ultraviolet B-induced inflammation in HaCaT keratinocytes and HR-1 hairless mice.
PubMed:Activation of several concurrent proapoptic pathways by sulforaphane in human colon cancer cells SW620.
PubMed:Sulforaphane but not ascorbigen, indole-3-carbinole and ascorbic acid activates the transcription factor Nrf2 and induces phase-2 and antioxidant enzymes in human keratinocytes in culture.
PubMed:The aliphatic isothiocyanates erucin and sulforaphane do not effectively up-regulate NAD(P)H:quinone oxidoreductase (NQO1) in human liver compared with rat.
PubMed:Gene expression profile of primary prostate epithelial and stromal cells in response to sulforaphane or iberin exposure.
PubMed:Modulation of phase II enzymes by sulforaphane: implications for its cardioprotective potential.
PubMed:Erucin, a new promising cancer chemopreventive agent from rocket salads, shows anti-proliferative activity on human lung carcinoma A549 cells.
PubMed:Interindividual differences in response to plant-based diets: implications for cancer risk.
PubMed:Involvement of KLF4 in sulforaphane- and iberin-mediated induction of p21(waf1/cip1).
PubMed:Bioavailability and kinetics of sulforaphane in humans after consumption of cooked versus raw broccoli.
PubMed:Polyamine metabolism and transforming growth factor-beta signaling are affected in Caco-2 cells by differentially cooked broccoli extracts.
PubMed:A food-derived synergist of NGF signaling: identification of protein tyrosine phosphatase 1B as a key regulator of NGF receptor-initiated signal transduction.
PubMed:Synergy between broccoli sprout extract and selenium in the upregulation of thioredoxin reductase in human hepatocytes.
PubMed:Application of high-speed countercurrent chromatography for the isolation of sulforaphane from broccoli seed meal.
PubMed:Modulation of rat hepatic and pulmonary cytochromes P450 and phase II enzyme systems by erucin, an isothiocyanate structurally related to sulforaphane.
PubMed:Role of reactive oxygen intermediates in cellular responses to dietary cancer chemopreventive agents.
PubMed:Regulation of estrogen receptor alpha expression in human breast cancer cells by sulforaphane.
PubMed:Broccoli consumption interacts with GSTM1 to perturb oncogenic signalling pathways in the prostate.
PubMed:Ochratoxin A impairs Nrf2-dependent gene expression in porcine kidney tubulus cells.
PubMed:Antigenotoxic properties of Eruca sativa (rocket plant), erucin and erysolin in human hepatoma (HepG2) cells towards benzo(a)pyrene and their mode of action.
PubMed:The diet-derived sulforaphane inhibits matrix metalloproteinase-9-activated human brain microvascular endothelial cell migration and tubulogenesis.
PubMed:Translating knowledge generated by epidemiological and in vitro studies into dietary cancer prevention.
PubMed:Direct and indirect antioxidant properties of inducers of cytoprotective proteins.
PubMed:Cytotoxic and antioxidant activity of 4-methylthio-3-butenyl isothiocyanate from Raphanus sativus L. (Kaiware Daikon) sprouts.
PubMed:Broccoli: a unique vegetable that protects mammalian hearts through the redox cycling of the thioredoxin superfamily.
PubMed:The influence of processing and preservation on the retention of health-promoting compounds in broccoli.
PubMed:Separation and purification of sulforaphane from broccoli seeds by solid phase extraction and preparative high-performance liquid chromatography.
PubMed:Evaluation of the safety and bioactivity of purified and semi-purified glucoraphanin.
PubMed:Keap1 eye on the target: chemoprevention of liver cancer.
PubMed:Biphasic modulation of cell proliferation by sulforaphane at physiologically relevant exposure times in a human colon cancer cell line.
PubMed:Consuming broccoli does not induce genes associated with xenobiotic metabolism and cell cycle control in human gastric mucosa.
PubMed:Diet, genetic polymorphisms, detoxification, and health risks.
PubMed:Molecular basis for chemoprevention by sulforaphane: a comprehensive review.
PubMed:The metabolic fate of purified glucoraphanin in F344 rats.
PubMed:Quantitative combination effects between sulforaphane and 3,3'-diindolylmethane on proliferation of human colon cancer cells in vitro.
PubMed:Kinetics of the stability of broccoli (Brassica oleracea Cv. Italica) myrosinase and isothiocyanates in broccoli juice during pressure/temperature treatments.
PubMed:Dual action of sulforaphane in the regulation of thioredoxin reductase and thioredoxin in human HepG2 and Caco-2 cells.
PubMed:Induction of GST and NQO1 in cultured bladder cells and in the urinary bladders of rats by an extract of broccoli (Brassica oleracea italica) sprouts.
PubMed:Phytochemicals induce breast cancer resistance protein in Caco-2 cells and enhance the transport of benzo[a]pyrene-3-sulfate.
PubMed:Effect of sulforaphane on cell growth, G(0)/G(1) phase cell progression and apoptosis in human bladder cancer T24 cells.
PubMed:Simultaneous determination of sulforaphane and its major metabolites from biological matrices with liquid chromatography-tandem mass spectroscopy.
PubMed:Fatal enterocolitis in Asian elephants (Elephas maximus) caused by Clostridium difficile.
PubMed:Evaporative light-scattering analysis of sulforaphane in broccoli samples: Quality of broccoli products regarding sulforaphane contents.
PubMed:Epithiospecifier protein from broccoli (Brassica oleracea L. ssp. italica) inhibits formation of the anticancer agent sulforaphane.
PubMed:Signaling pathways and intracellular targets of sulforaphane mediating cell cycle arrest and apoptosis.
PubMed:Effect of isothiocyanates on nuclear accumulation of NF-kappaB, Nrf2, and thioredoxin in caco-2 cells.
PubMed:Aqueous extracts of selenium-fertilized broccoli increase selenoprotein activity and inhibit DNA single-strand breaks, but decrease the activity of quinone reductase in Hepa 1c1c7 cells.
PubMed:Glutathione S-transferase M1 polymorphism and metabolism of sulforaphane from standard and high-glucosinolate broccoli.
PubMed:ERK and JNK signaling pathways are involved in the regulation of activator protein 1 and cell death elicited by three isothiocyanates in human prostate cancer PC-3 cells.
PubMed:Chinese cabbage extracts and sulforaphane can protect H2O2-induced inhibition of gap junctional intercellular communication through the inactivation of ERK1/2 and p38 MAP kinases.
PubMed:Cultivation conditions and selenium fertilization alter the phenolic profile, glucosinolate, and sulforaphane content of broccoli.
PubMed:Induction of quinone reductase by sulforaphane and sulforaphane N-acetylcysteine conjugate in murine hepatoma cells.
PubMed:Isothiocyanates induce cell cycle arrest, apoptosis and mitochondrial potential depolarization in HL-60 and multidrug-resistant cell lines.
PubMed:Transcriptome analysis of human colon Caco-2 cells exposed to sulforaphane.
PubMed:Effect of sulforaphane on metallothionein expression and induction of apoptosis in human hepatoma HepG2 cells.
PubMed:Phytochemicals in broccoli transcriptionally induce thioredoxin reductase.
PubMed:Role of PI3K/Akt and MEK/ERK signaling pathways in sulforaphane- and erucin-induced phase II enzymes and MRP2 transcription, G2/M arrest and cell death in Caco-2 cells.
PubMed:Selenium enrichment of broccoli: interactions between selenium and secondary plant compounds.
PubMed:Direct antioxidant activity of purified glucoerucin, the dietary secondary metabolite contained in rocket (Eruca sativa Mill.) seeds and sprouts.
PubMed:Sulforaphane, erucin, and iberin up-regulate thioredoxin reductase 1 expression in human MCF-7 cells.
PubMed:Effects of dietary chemopreventive phytochemicals on P-glycoprotein function.
PubMed:Cruciferous vegetables, genetic polymorphisms in glutathione S-transferases M1 and T1, and prostate cancer risk.
PubMed:Broccoli consumption and chronic atrophic gastritis among Japanese males: an epidemiological investigation.
PubMed:Sulforaphane inhibits human MCF-7 mammary cancer cell mitotic progression and tubulin polymerization.
PubMed:Inhibition of mutagenicity of food-derived heterocyclic amines by sulforaphane--a constituent of broccoli.
PubMed:Heating decreases epithiospecifier protein activity and increases sulforaphane formation in broccoli.
PubMed:Modulatory properties of various natural chemopreventive agents on the activation of NF-kappaB signaling pathway.
PubMed:Effects of different processing methods on induction of quinone reductase by dietary broccoli in rats.
PubMed:Interactions between sulforaphane and apigenin in the induction of UGT1A1 and GSTA1 in CaCo-2 cells.
PubMed:Induction of phase II detoxification enzymes in rats by plant-derived isothiocyanates: comparison of allyl isothiocyanate with sulforaphane and related compounds.
PubMed:Glucoraphanin and 4-hydroxyglucobrassicin contents in seeds of 59 cultivars of broccoli, raab, kohlrabi, radish, cauliflower, brussels sprouts, kale, and cabbage.
PubMed:Sulforaphane: a naturally occurring mammary carcinoma mitotic inhibitor, which disrupts tubulin polymerization.
PubMed:Sulforaphane and quercetin modulate PhIP-DNA adduct formation in human HepG2 cells and hepatocytes.
PubMed:Analysis of isothiocyanate mercapturic acids in urine: a biomarker for cruciferous vegetable intake.
PubMed:Absorption/metabolism of sulforaphane and quercetin, and regulation of phase II enzymes, in human jejunum in vivo.
PubMed:Food matrix effects on bioactivity of broccoli-derived sulforaphane in liver and colon of F344 rats.
PubMed:Synergy between sulforaphane and selenium in the induction of thioredoxin reductase 1 requires both transcriptional and translational modulation.
PubMed:The effect of post-harvest and packaging treatments on glucoraphanin concentration in broccoli (Brassica oleracea var. italica).
PubMed:Plant-derived biomolecules in fermented cabbage.
PubMed:Influence of temperature and ontogeny on the levels of glucosinolates in broccoli (Brassica oleracea Var. italica) sprouts and their effect on the induction of mammalian phase 2 enzymes.
PubMed:Sulforaphane and its glutathione conjugate but not sulforaphane nitrile induce UDP-glucuronosyl transferase (UGT1A1) and glutathione transferase (GSTA1) in cultured cells.
PubMed:Induction of xenobiotic enzymes by the MAP kinase pathway and the antioxidant or electrophile response element (ARE/EpRE).
PubMed:Comparison of the bioactivity of two glucoraphanin hydrolysis products found in broccoli, sulforaphane and sulforaphane nitrile.
PubMed:A sulforaphane analogue that potently activates the Nrf2-dependent detoxification pathway.
PubMed:Effects of cruciferous vegetables and their constituents on drug metabolizing enzymes involved in the bioactivation of DNA-reactive dietary carcinogens.
PubMed:Preparative HPLC method for the purification of sulforaphane and sulforaphane nitrile from Brassica oleracea.
PubMed:The importance of using scientific principles in the development of medicinal agents from plants.
PubMed:Chemoprotection by organosulfur inducers of phase 2 enzymes: dithiolethiones and dithiins.
PubMed:Inhibition of benzo[a]pyrene- and 1,6-dinitropyrene-DNA adduct formation in human mammary epithelial cells bydibenzoylmethane and sulforaphane.
PubMed:Progress in cancer chemoprevention: development of diet-derived chemopreventive agents.
PubMed:Thermal degradation of sulforaphane in aqueous solution.
PubMed:Antioxidant functions of sulforaphane: a potent inducer of Phase II detoxication enzymes.
PubMed:Broccoli sprouts in cancer prevention.
PubMed:Food fights. Is it a drug or a carrot stick?
Sulforaphane (SFN) is the most characterized isothiocyanate. SFN has received a great deal of attention because of its ability to simultaneously modulate multiple cellular targets involved in cancer development, including: (i) DNA protection by modulating carcinogen-metabolizing enzymes and blocking the action of mutagens; (ii) inhibition of cell proliferation and induction of apoptosis, thereby retarding or eliminating clonal expansion of initiated, transformed, and/or neoplastic cells; (iii) inhibition of neoangiogenesis, progression of benign tumors to malignant tumors, and metastasis formation. SFN is therefore able to prevent, delay, or reverse preneoplastic lesions, as well as to act on cancer cells as a therapeutic agent. Taking into account this evidence and its favorable toxicological profile, SFN can be viewed as a conceptually promising agent in cancer prevention and/or therapy. SFN is the hydrolysis product of glucoraphanin, particularly high in the young sprouts of broccoli and cauliflower. SFN can also be obtained by eating cruciferous vegetables such as brussel sprouts, broccoli, cauliflower, bok choy, kale, collards, arugula, broccoli sprouts, chinese broccoli, broccoli raab, kohlrabi, mustard, turnip, radish, watercress and cabbage. (PMID: 17134937) [HMDB]
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