Identification

Namebenzyl isothiocyanate
IUPACisothiocyanatomethylbenzene
CAS Number622-78-6
EINECS210-753-9
FDA UNII871J6YOR8Q
Molecular FormulaC8 H7 N S
Molecular Weight149.21579000
MDL NumberMFCD00004819
Nikkaji NumberJ6.842J
Beilstein0386135
CoE Number11863
XlogP33.20 (est)

Regulatory

JECFA Food Flavoring1562 benzyl isothiocyanate
DG SANTE Food Flavourings12.102 benzyl isothiocyanate
FEMA Number4428
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)622-78-6 ; BENZYL ISOTHIOCYANATE

Physical Properties

Appearance colorless to pale yellow clear liquid (est)
Assay 97.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 1.12100 to 1.12700 @ 25.00 °C.
Pounds per Gallon - (est). 9.328 to 9.378
Refractive Index 1.60000 to 1.60600 @ 20.00 °C.
Melting Point 41.00 °C. @ 760.00 mm Hg
Boiling Point 242.00 to 243.00 °C. @ 760.00 mm Hg, 140.00 to 141.00 °C. @ 17.00 mm Hg
Acid Value 1.00 max. KOH/g
Vapor Pressure 0.020000 mmHg @ 20.00 °C.
Flash Point 212.00 °F. TCC ( 100.00 °C. )
logP (o/w) 3.160
Soluble in alcohol
Similar Items note

Organoleptic Properties

Odor Strength medium ,
Substantivity 15 hour(s) at 0.10 % in dipropylene glycol
Odor Description at 0.10 % in dipropylene glycol.
Odor sample from Sigma-Aldrich
Taste Description spicy green plastic horseradish watercress nasturtium capers

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityintraperitoneal-mouse LDLo 100 mg/kg
Dermal Toxicitysubcutaneous-mouse LD50 150 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavoring agents
Recommendation for benzyl isothiocyanate usage levels up tonot for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU)0.95 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA)0.40 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI)96 (μg/person/day)
Threshold of Concern540 (μg/person/day)
baked goods0.40000
beverages(nonalcoholic)0.20000
beverages(alcoholic)-
breakfast cereal0.20000
cheese0.40000
chewing gum-
condiments / relishes0.20000
confectionery froastings0.40000
egg products-
fats / oils0.20000
fish products0.10000
frozen dairy0.40000
fruit ices0.40000
gelatins / puddings1.00000
granulated sugar-
gravies1.00000
hard candy-
imitation dairy0.40000
instant coffee / tea-
jams / jellies1.00000
meat products0.10000
milk products0.40000
nut products-
other grains0.20000
poultry0.10000
processed fruits0.30000
processed vegetables-
reconstituted vegetables-
seasonings / flavors0.20000
snack foods0.20000
soft candy-
soups0.20000
sugar substitutes-
sweet sauces0.20000
Dairy products, excluding products of category 02.0 (01.0)0.40000
Fats and oils, and fat emulsions (type water-in-oil) (02.0)0.20000
Edible ices, including sherbet and sorbet (03.0)0.40000
Processed fruit (04.1)0.30000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2)-
Confectionery (05.0)0.40000
Chewing gum (05.3)-
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0)0.20000
Bakery wares (07.0)0.40000
Meat and meat products, including poultry and game (08.0)0.10000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0)0.10000
Eggs and egg products (10.0)-
Sweeteners, including honey (11.0)-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0)0.20000
Foodstuffs intended for particular nutritional uses (13.0)0.40000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1)-
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2)0.40000
Ready-to-eat savouries (15.0)1.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0)0.20000

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Potential Uses

FL papaya watercress nasturtium

Natural Occurrence

allamanda cathartica linn. flower oil brazil @ 8.70% Data cabbage leaf cress common cress plant cress garden cress plant cress indian cress marango root moringa root onion bulb papaya fruit papaya seed watercress

Synonyms

benzene, (isothiocyanatomethyl)- benzyl isothio cyanate benzyl mustard benzyl mustard oil benzylisothiocyanate phenylmethanisothiocyanate phenylmethyl isothiocyanate iso thiocyanatomethyl-benzene (iso thiocyanatomethyl) benzene (iso thiocyanatomethyl)benzene (iso thiocyanatomethyl)benzol iso thiocyanatomethylbenzene a-iso thiocyanatotoluene alpha-iso thiocyanatotoluene iso thiocyanic acid benzyl ester iso thiocyanic acid, benzyl ester toluene, a-isothiocyanato- tromacaps tromalyt urogran Info: miscellaneous nitrogen derivatives PubMed: Benzyl isothiocyanate inhibits IL-13 expression in human basophilic KU812 cells. J-Stage: a-Tocopherol Sensitizes Human Leukemia HL-60 Cells to Apoptosis Induced by Benzyl Isothiocyanate PubMed: Chemo-predictive assay for targeting cancer stem-like cells in patients affected by brain tumors. PubMed: Purification of Active Myrosinase from Plants by Aqueous Two-Phase Counter-Current Chromatography. PubMed: Glycyl endopeptidase from papaya latex: partial purification and use for production of fish gelatin hydrolysate. PubMed: Efficient 1-Step Radiolabeling of Monoclonal Antibodies to High Specific Activity with 225Ac for α-Particle Radioimmunotherapy of Cancer. PubMed: Stable, water extractable isothiocyanates from Moringa oleifera leaves attenuate inflammation in vitro. PubMed: Benzyl isothiocyanate suppresses high-fat diet-stimulated mammary tumor progression via the alteration of tumor microenvironments in obesity-resistant BALB/c mice. PubMed: Antiinflammatory activity of glucomoringin isothiocyanate in a mouse model of experimental autoimmune encephalomyelitis. PubMed: Review: an exposition of medicinal preponderance of Moringa oleifera (Lank.). PubMed: Cytotoxic effect of Reseda lutea L.: A case of forgotten remedy. PubMed: In vitro and in vivo studies of trypanocidal activity of dietary isothiocyanates. PubMed: Benzyl isothiocyanate inhibits HNSCC cell migration and invasion, and sensitizes HNSCC cells to cisplatin. PubMed: Antitrypanosomal isothiocyanate and thiocarbamate glycosides from Moringa peregrina. PubMed: A chemical approach for the reduction of beauvericin in a solution model and in food systems. PubMed: Antibacterial activity of glucomoringin bioactivated with myrosinase against two important pathogens affecting the health of long-term patients in hospitals. PubMed: Odour-active compounds in papaya fruit cv. Red Maradol. PubMed: Insights into the mode of action of benzyl isothiocyanate on Campylobacter jejuni. PubMed: Oral administration of benzyl-isothiocyanate inhibits in vivo growth of subcutaneous xenograft tumors of human malignant melanoma A375.S2 cells. PubMed: Determination of benzyl isothiocyanate metabolites in human plasma and urine by LC-ESI-MS/MS after ingestion of nasturtium (Tropaeolum majus L.). PubMed: Benzyl isothiocyanate: double trouble for breast cancer cells. PubMed: Isothiocyanates protect against oxidized LDL-induced endothelial dysfunction by upregulating Nrf2-dependent antioxidation and suppressing NFκB activation. PubMed: Inhibitory effect of benzyl isothiocyanate on proliferation in vitro of human glioma cells. PubMed: Dietary chemopreventative benzyl isothiocyanate inhibits breast cancer stem cells in vitro and in vivo. PubMed: High-performance liquid chromatographic enantioseparation of (RS)-bupropion using isothiocyanate-based chiral derivatizing reagents. PubMed: Downregulation of Mcl-1 through inhibition of translation contributes to benzyl isothiocyanate-induced cell cycle arrest and apoptosis in human leukemia cells. PubMed: Antimicrobial isothiocyanates from the seeds of Moringa oleifera Lam. PubMed: Suppression of FOXQ1 in benzyl isothiocyanate-mediated inhibition of epithelial-mesenchymal transition in human breast cancer cells. PubMed: Study of the chemical reduction of the fumonisins toxicity using allyl, benzyl and phenyl isothiocyanate in model solution and in food products. PubMed: Stability of benzylic-type isothiocyanates in hydrodistillation-mimicking conditions. PubMed: Benzyl isothiocyanate induces protective autophagy in human prostate cancer cells via inhibition of mTOR signaling. PubMed: Apoptosis induced by benzyl isothiocyanate in gefitinib-resistant lung cancer cells is associated with Akt/MAPK pathways and generation of reactive oxygen species. PubMed: Erucin and benzyl isothiocyanate suppress growth of late stage primary human ovarian carcinoma cells and telomerase activity in vitro. PubMed: Isothiocyanates ameliorate the symptom of heart dysfunction and mortality in a murine AIDS model by inhibiting apoptosis in the left ventricle. PubMed: Antimicrobial activities of isothiocyanates against Campylobacter jejuni isolates. PubMed: Development and application of a method for identification of isothiocyanate-targeted molecules in colon cancer cells. PubMed: Benzyl isothiocyanate disturbs lipid metabolism in rats in a way independent of its thyroid impact following in vivo long-term treatment and in vitro adipocytes studies. PubMed: Identifying and characterizing binding sites on the irreversible inhibition of human glutathione S-transferase P1-1 by S-thiocarbamoylation. PubMed: Proteomic analysis of covalent modifications of tubulins by isothiocyanates. PubMed: Enhancement of cisplatin cytotoxicity by benzyl isothiocyanate in HL-60 cells. PubMed: Notch2 activation by benzyl isothiocyanate impedes its inhibitory effect on breast cancer cell migration. PubMed: Benzyl isothiocyanate causes FoxO1-mediated autophagic death in human breast cancer cells. PubMed: Critical role of p53 upregulated modulator of apoptosis in benzyl isothiocyanate-induced apoptotic cell death. PubMed: α-Tocopherol sensitizes human leukemia HL-60 cells to apoptosis induced by benzyl isothiocyanate. PubMed: Content determination of benzyl glucosinolate and anti-cancer activity of its hydrolysis product in Carica papaya L. PubMed: Cytotoxicity of benzyl isothiocyanate in normal renal proximal tubular cells and its modulation by glutathione. PubMed: Hepatoma-derived growth factor regulates breast cancer cell invasion by modulating epithelial--mesenchymal transition. PubMed: Benzyl isothiocyanate (BITC) induces G2/M phase arrest and apoptosis in human melanoma A375.S2 cells through reactive oxygen species (ROS) and both mitochondria-dependent and death receptor-mediated multiple signaling pathways. PubMed: Contact and fumigant toxicity of Armoracia rusticana essential oil, allyl isothiocyanate and related compounds to Dermatophagoides farinae. PubMed: Benzyl isothiocyanate suppresses pancreatic tumor angiogenesis and invasion by inhibiting HIF-α/VEGF/Rho-GTPases: pivotal role of STAT-3. PubMed: Nanoemulsions of cancer chemopreventive agent benzyl isothiocyanate display enhanced solubility, dissolution, and permeability. PubMed: Benzyl isothiocyanate inhibits basal and hepatocyte growth factor-stimulated migration of breast cancer cells. PubMed: Validated high-performance liquid chromatographic enantioseparation of selenomethionine using isothiocyanate based chiral derivatizing reagents. PubMed: Varied response of Spodoptera littoralis against Arabidopsis thaliana with metabolically engineered glucosinolate profiles. PubMed: Benzyl isothiocyanate sensitizes human pancreatic cancer cells to radiation by inducing apoptosis. PubMed: Benzyl isothiocyanate, a major component from the roots of Salvadora persica is highly active against Gram-negative bacteria. PubMed: Dietary isothiocyanate-induced apoptosis via thiol modification of DNA topoisomerase IIα. PubMed: Engineering GST M2-2 for high activity with indene 1,2-oxide and indication of an H-site residue sustaining catalytic promiscuity. PubMed: MicroRNA-375 and MicroRNA-221: Potential Noncoding RNAs Associated with Antiproliferative Activity of Benzyl Isothiocyanate in Pancreatic Cancer. PubMed: Inhibition of lipopolysaccharide-induced cyclooxygenase-2 and inducible nitric oxide synthase expression by 4-[(2'-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate from Moringa oleifera. PubMed: Mitogen-activated protein kinase mediates the apoptosis of highly metastatic human non-small cell lung cancer cells induced by isothiocyanates. PubMed: Synthesis and antiproliferative activity of novel α- and β-dialkoxyphosphoryl isothiocyanates. PubMed: Phenethyl isothiocyanate sensitizes human cervical cancer cells to apoptosis induced by cisplatin. PubMed: Characteristics of papaya seed oils obtained by extrusion-expelling processes. PubMed: Evaluation of antibacterial activity of 3-butenyl, 4-pentenyl, 2-phenylethyl, and benzyl isothiocyanate in Brassica vegetables. PubMed: Benzyl isothiocyanate inhibits epithelial-mesenchymal transition in cultured and xenografted human breast cancer cells. PubMed: Assessment of the protective effects of selected dietary anticarcinogens against DNA damage and cytogenetic effects induced by benzo[a]pyrene in C57BL/6J mice. PubMed: Benzyl isothiocyanate (BITC) and phenethyl isothiocyanate (PEITC)-mediated generation of reactive oxygen species causes cell cycle arrest and induces apoptosis via activation of caspase-3, mitochondria dysfunction and nitric oxide (NO) in human osteogenic sarcoma U-2 OS cells. PubMed: Pancreatic tumor suppression by benzyl isothiocyanate is associated with inhibition of PI3K/AKT/FOXO pathway. PubMed: Stimulation of phagocytosis by sulforaphane. PubMed: The roles of AIF and Endo G in the apoptotic effects of benzyl isothiocyanate on DU 145 human prostate cancer cells via the mitochondrial signaling pathway. PubMed: Oral administration of benzyl-isothiocyanate inhibits solid tumor growth and lung metastasis of 4T1 murine mammary carcinoma cells in BALB/c mice. PubMed: Benzyl isothiocyanate inhibits oncogenic actions of leptin in human breast cancer cells by suppressing activation of signal transducer and activator of transcription 3. PubMed: Effectiveness of different solid-phase microextraction fibres for differentiation of selected Madeira island fruits based on their volatile metabolite profile--identification of novel compounds. PubMed: Isothiocyanates inhibit proteasome activity and proliferation of multiple myeloma cells. PubMed: Characterization and antimicrobial activity of 4-(β-D-glucopyranosyl-1→4-α-L-rhamnopyranosyloxy)-benzyl thiocarboxamide; a novel bioactive compound from Moringa oleifera seed extract. PubMed: The toxic effects of benzyl glucosinolate and its hydrolysis product, the biofumigant benzyl isothiocyanate, to Folsomia fimetaria. PubMed: Sensitization of non-small cell lung cancer cells to cisplatin by naturally occurring isothiocyanates. PubMed: Potential anti-inflammatory phenolic glycosides from the medicinal plant Moringa oleifera fruits. PubMed: BITC Sensitizes Pancreatic Adenocarcinomas to TRAIL-induced Apoptosis. PubMed: Candidate dietary phytochemicals modulate expression of phase II enzymes GSTP1 and NQO1 in human lung cells. PubMed: Isothiocyanates induce oxidative stress and suppress the metastasis potential of human non-small cell lung cancer cells. PubMed: Benzyl isothiocyanate (BITC) inhibits migration and invasion of human gastric cancer AGS cells via suppressing ERK signal pathways. PubMed: p53-Independent apoptosis by benzyl isothiocyanate in human breast cancer cells is mediated by suppression of XIAP expression. PubMed: Benzyl isothiocyanate-mediated inhibition of histone deacetylase leads to NF-kappaB turnoff in human pancreatic carcinoma cells. PubMed: Preclinical evaluation of monoclonal antibody 14C5 for targeting pancreatic cancer. PubMed: Inhibition of human breast cancer xenograft growth by cruciferous vegetable constituent benzyl isothiocyanate. PubMed: Trypanocidal and antileukaemic effects of the essential oils of Hagenia abyssinica, Leonotis ocymifolia, Moringa stenopetala, and their main individual constituents. PubMed: Immunochemical detection of food-derived isothiocyanate as a lysine conjugate. PubMed: Benzyl isothiocyanate (BITC) inhibits migration and invasion of human colon cancer HT29 cells by inhibiting matrix metalloproteinase-2/-9 and urokinase plasminogen (uPA) through PKC and MAPK signaling pathway. PubMed: New biomarkers for monitoring the levels of isothiocyanates in humans. PubMed: [Antimicrobial efficacy of benzyl isothiocyanate]. PubMed: Inhibition of apoptosis in human retinal pigment epithelial cells treated with benzo(e)pyrene, a toxic component of cigarette smoke. PubMed: Prevention of mammary carcinogenesis in MMTV-neu mice by cruciferous vegetable constituent benzyl isothiocyanate. PubMed: Growth-inhibiting activities of phenethyl isothiocyanate and its derivatives against intestinal bacteria. PubMed: Benzyl isothiocyanate exhibits anti-inflammatory effects in murine macrophages and in mouse skin. PubMed: Differing mechanisms of simple nitrile formation on glucosinolate degradation in Lepidium sativum and Nasturtium officinale seeds. PubMed: A new class of isothiocyanate-based irreversible inhibitors of macrophage migration inhibitory factor. PubMed: Dietary agent, benzyl isothiocyanate inhibits signal transducer and activator of transcription 3 phosphorylation and collaborates with sulforaphane in the growth suppression of PANC-1 cancer cells. PubMed: Aggresome-like structure induced by isothiocyanates is novel proteasome-dependent degradation machinery. PubMed: Anti-proliferative and proapoptotic effects of benzyl isothiocyanate on human pancreatic cancer cells is linked to death receptor activation and RasGAP/Rac1 down-modulation. PubMed: Benzyl isothiocyanate-mediated generation of reactive oxygen species causes cell cycle arrest and induces apoptosis via activation of MAPK in human pancreatic cancer cells. PubMed: Re: The role of STAT-3 in the induction of apoptosis in pancreatic cancer cells by benzyl isothiocyanate. PubMed: Benzyl isothiocyanate sensitizes human pancreatic cancer cells to radiation therapy. PubMed: Diverse chemicals including aryl hydrocarbon receptor ligands modulate transcriptional activity of the 3'immunoglobulin heavy chain regulatory region. PubMed: Phytochemical induction of cell cycle arrest by glutathione oxidation and reversal by N-acetylcysteine in human colon carcinoma cells. PubMed: Cancer preventive isothiocyanates induce selective degradation of cellular alpha- and beta-tubulins by proteasomes. PubMed: The antimicrobial effects of glucosinolates and their respective enzymatic hydrolysis products on bacteria isolated from the human intestinal tract. PubMed: Benzyl isothiocyanate inhibits murine WEHI-3 leukemia cells in vitro and promotes phagocytosis in BALB/c mice in vivo. PubMed: Degradation and sorption of 2-propenyl and benzyl isothiocyanate in soil. PubMed: Isothiocyanate profile and selective antibacterial activity of root, stem, and leaf extracts derived from Raphanus sativus L. PubMed: The role of STAT-3 in the induction of apoptosis in pancreatic cancer cells by benzyl isothiocyanate. PubMed: Isothiocyanates repress estrogen receptor alpha expression in breast cancer cells. PubMed: Binding to protein by isothiocyanates: a potential mechanism for apoptosis induction in human non small lung cancer cells. PubMed: (-)-Epigallocatechin-3-gallate potentiates the cytotoxicity induced by benzyl isothiocyanate and hydrogen peroxide in human Jurkat T lymphocytes. PubMed: Acaricidal constituents isolated from Sinapis alba L. seeds and structure-activity relationships. PubMed: Benzylglucosinolate, benzylisothiocyanate, and myrosinase activity in papaya fruit during development and ripening. PubMed: Dietary isothiocyanate mediated apoptosis of human cancer cells is associated with Bcl-xL phosphorylation. PubMed: Benzyl isothiocyanate targets mitochondrial respiratory chain to trigger reactive oxygen species-dependent apoptosis in human breast cancer cells. PubMed: ATP depletion alters the mode of cell death induced by benzyl isothiocyanate. PubMed: Benzyl isothiocyanate inhibits metalloproteinase-2/-9 expression by suppressing the mitogen-activated protein kinase in SK-Hep1 human hepatoma cells. PubMed: Glutathione- and thioredoxin-related enzymes are modulated by sulfur-containing chemopreventive agents. PubMed: Modifying effects of dietary factors on (-)-epigallocatechin-3-gallate-induced pro-matrix metalloproteinase-7 production in HT-29 human colorectal cancer cells. PubMed: Formation and degradation kinetics of the biofumigant benzyl isothiocyanate in soil. PubMed: Comments regarding: Benzyl isothiocyanate (BITC) induces apoptosis in ovarian cancer cells in vitro Kalkunte S, Swamy N, Dizon DS, Brard L. J Exp Ther Oncol.5(4):287-300, 2006. PubMed: Papaya seed represents a rich source of biologically active isothiocyanate. PubMed: Benzyl isothiocyanate-induced apoptosis in human breast cancer cells is initiated by reactive oxygen species and regulated by Bax and Bak. PubMed: Selective cytotoxicity of benzyl isothiocyanate in the proliferating fibroblastoid cells. PubMed: Benzyl isothiocyanate-induced DNA damage causes G2/M cell cycle arrest and apoptosis in human pancreatic cancer cells. PubMed: p38MAPK mediates benzyl isothiocyanate-induced p21WAF1 expression in vascular smooth muscle cells via the regulation of Sp1. PubMed: Benzyl isothiocyanate (BITC) induces apoptosis in ovarian cancer cells in vitro. PubMed: Cell death induction by isothiocyanates and their underlying molecular mechanisms. PubMed: Haplotype-environment interactions that regulate the human glutathione S-transferase P1 promoter. PubMed: Newly constructed stable reporter cell lines for mechanistic studies on electrophile-responsive element-mediated gene expression reveal a role for flavonoid planarity. PubMed: Molecular cloning of AbGst1 encoding a glutathione transferase differentially expressed during exposure of Alternaria brassicicola to isothiocyanates. PubMed: Raphanus sativus and its isothiocyanates inhibit vascular smooth muscle cells proliferation and induce G(1) cell cycle arrest. PubMed: Characterization of two Arabidopsis thaliana glutathione S-transferases. PubMed: The principal urinary metabolites of dietary isothiocyanates, N-acetylcysteine conjugates, elicit the same anti-proliferative response as their parent compounds in human bladder cancer cells. PubMed: Effect of isothiocyanates on nuclear accumulation of NF-kappaB, Nrf2, and thioredoxin in caco-2 cells. PubMed: Protective effects of benzyl isothiocyanate and sulforaphane but not resveratrol against initiation of pancreatic carcinogenesis in hamsters. PubMed: Dietary isothiocyanates modify mitochondrial functions through their electrophilic reaction. PubMed: Effects of benzyl and phenethyl isothiocyanate on P450s 2A6 and 2A13: potential for chemoprevention in smokers. PubMed: (89)Zr as a PET surrogate radioisotope for scouting biodistribution of the therapeutic radiometals (90)Y and (177)Lu in tumor-bearing nude mice after coupling to the internalizing antibody cetuximab. PubMed: Modulation of jejunal contractions by extract of Carica papaya L. seeds. PubMed: The role of c-Jun in the AP-1 activation induced by naturally occurring isothiocyanates. PubMed: The identification of 1,3-oxazolidine-2-thiones and 1,3-thiazolidine-2-thiones from the reaction of glucose with benzyl isothiocyanate. PubMed: Benzyl isothiocyanate inhibits oxidative stress in mouse skin: Involvement of attenuation of leukocyte infiltration. PubMed: Benzyl isothiocyanate modifies expression of the G2/M arrest-related genes. PubMed: A novel function of benzyl isothiocyanate in vascular smooth muscle cells: the role of ERK1/2, cell cycle regulation, and matrix metalloproteinase-9. PubMed: Dietary isothiocyanates inhibit Caco-2 cell proliferation and induce G2/M phase cell cycle arrest, DNA damage, and G2/M checkpoint activation. PubMed: Potential chemoprotective effects of the coffee components kahweol and cafestol palmitates via modification of hepatic N-acetyltransferase and glutathione S-transferase activities. PubMed: Induction of apoptosis in a non-small cell human lung cancer cell line by isothiocyanates is associated with P53 and P21. PubMed: Glutathione S-transferase Pi has at least three distinguishable xenobiotic substrate sites close to its glutathione-binding site. PubMed: Dietary organic isothiocyanates are cytotoxic in human breast cancer MCF-7 and mammary epithelial MCF-12A cell lines. PubMed: Do aberrant crypt foci have predictive value for the occurrence of colorectal tumours? Potential of gene expression profiling in tumours. PubMed: Cysteine/cystine couple is a newly recognized node in the circuitry for biologic redox signaling and control. PubMed: Cell cycle arrest, apoptosis induction and inhibition of nuclear factor kappa B activation in anti-proliferative activity of benzyl isothiocyanate against human pancreatic cancer cells. PubMed: Pregnancy outcomes following pre- and post-implantation exposure of Sprague-Dawley rats to benzyl isothiocyanate. PubMed: A link between benzyl isothiocyanate-induced cell cycle arrest and apoptosis: involvement of mitogen-activated protein kinases in the Bcl-2 phosphorylation. PubMed: Effect of benzyl isothiocyanate on spontaneous and induced force of rat uterine contraction. PubMed: In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products. PubMed: Benzyl isothiocyanate inhibits excessive superoxide generation in inflammatory leukocytes: implication for prevention against inflammation-related carcinogenesis. PubMed: Tocolytic and toxic activity of papaya seed extract on isolated rat uterus. PubMed: Enhancement of urinary bladder carcinogenesis by combined treatment with benzyl isothiocyanate and N-butyl-N-(4-hydroxybutyl)nitrosamine in rats after initiation. PubMed: Influence of plant and bacterial myrosinase activity on the metabolic fate of glucosinolates in gnotobiotic rats. PubMed: Requirement of a carbon spacer in benzyl isothiocyanate-mediated cytotoxicity and MAPK activation in head and neck squamous cell carcinoma. PubMed: Involvement of toxicity as an early event in urinary bladder carcinogenesis induced by phenethyl isothiocyanate, benzyl isothiocyanate, and analogues in F344 rats. PubMed: Enhancement of glutathione and g-glutamylcysteine synthetase, the rate limiting enzyme of glutathione synthesis, by chemoprotective plant-derived food and beverage components in the human hepatoma cell line HepG2. PubMed: Effects of selected food factors with chemopreventive properties on combined lipopolysaccharide- and interferon-gamma-induced IkappaB degradation in RAW264.7 macrophages. PubMed: Effects of benzyl isothiocyanate and 2-phenethyl isothiocyanate on benzo[a]pyrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism in F-344 rats. PubMed: Effects of garden and water cress juices and their constituents, benzyl and phenethyl isothiocyanates, towards benzo(a)pyrene-induced DNA damage: a model study with the single cell gel electrophoresis/Hep G2 assay. PubMed: Effect of organic isothiocyanates on the P-glycoprotein- and MRP1-mediated transport of daunomycin and vinblastine. PubMed: Simultaneous treatment with benzyl isothiocyanate, a strong bladder promoter, inhibits rat urinary bladder carcinogenesis by N-butyl-N-(4-hydroxybutyl)nitrosamine. PubMed: Benzyl isothiocyanate: an effective inhibitor of polycyclic aromatic hydrocarbon tumorigenesis in A/J mouse lung. PubMed: Effects of benzyl isothiocyanate and phenethyl isothiocyanate on DNA adduct formation by a mixture of benzo[a]pyrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mouse lung. PubMed: Effects of papaya seed extract and benzyl isothiocyanate on vascular contraction. PubMed: Effect of naturally occurring organosulfur compounds on nitric oxide production in lipopolysaccharide-activated macrophages. PubMed: Palladium(0)-catalyzed enantioselective O,S-rearrangement of racemic O-allylic thiocarbamates: a new entry to enantioenriched allylic sulfur compounds. PubMed: Toxic effects of benzyl and allyl isothiocyanates and benzyl-isoform specific metabolites in the urinary bladder after a single intravesical application to rats. PubMed: Inhibition of benzo(a)pyrene-induced lung tumorigenesis in A/J mice by dietary N-acetylcysteine conjugates of benzyl and phenethyl isothiocyanates during the postinitiation phase is associated with activation of mitogen-activated protein kinases and p53 activity and induction of apoptosis. PubMed: Involvement of the mitochondrial death pathway in chemopreventive benzyl isothiocyanate-induced apoptosis. PubMed: 4-(Methylthio)-3-butenyl isothiocyanate, a principal antimutagen in daikon (Raphanus sativus; Japanese white radish). PubMed: Decomposition rates of isothiocyanate conjugates determine their activity as inhibitors of cytochrome p450 enzymes. PubMed: Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines. PubMed: Differential effects of naturally occurring isothiocyanates on the activities of cytochrome P450 2E1 and the mutant P450 2E1 T303A. PubMed: Benzyl isothiocyanate is the chief or sole anthelmintic in papaya seed extracts. PubMed: Successful and not so successful chemoprevention of tobacco smoke-induced lung tumors. PubMed: Effects of phenethyl isothiocyanate and benzyl isothiocyanate, individually and in combination, on lung tumorigenesis induced in A/J mice by benzo[a]pyrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. PubMed: Inactivation of cytochrome P450 2B1 by benzyl isothiocyanate, a chemopreventative agent from cruciferous vegetables. PubMed: Effects of benzyl isothiocyanate on rat and human cytochromes P450: identification of metabolites formed by P450 2B1. PubMed: Effects of benzyl isothiocyanate and phenethyl isothiocyanate on benzo[a]pyrene metabolism and DNA adduct formation in the A/J mouse. PubMed: A glutathione S-transferase inducer from papaya: rapid screening, identification and structure-activity relationship of isothiocyanates. PubMed: Chemoprevention of tobacco-smoke lung carcinogenesis in mice after cessation of smoke exposure. PubMed: Mechanism of oxidative DNA damage induced by carcinogenic allyl isothiocyanate. PubMed: Chemoprevention of aflatoxin B1 hepatocarcinogenesis by coumarin, a natural benzopyrone that is a potent inducer of aflatoxin B1-aldehyde reductase, the glutathione S-transferase A5 and P1 subunits, and NAD(P)H:quinone oxidoreductase in rat liver. PubMed: Redox regulation of glutathione S-transferase induction by benzyl isothiocyanate: correlation of enzyme induction with the formation of reactive oxygen intermediates. PubMed: Glutathione redox potential in response to differentiation and enzyme inducers. PubMed: Isothiocyanates and freeze-dried strawberries as inhibitors of esophageal cancer. PubMed: Genotoxic effects of benzyl isothiocyanate, a natural chemopreventive agent. PubMed: Dietary compounds that induce cancer preventive phase 2 enzymes activate apoptosis at comparable doses in HT29 colon carcinoma cells. PubMed: Inactivation of cytochrome P450 2E1 by benzyl isothiocyanate. PubMed: Antimicrobial components of some cruciferae plants (Diplotaxis harra Forsk. and Erucaria microcarpa Boiss.) PubMed: An antitumor promoter from Moringa oleifera Lam. PubMed: Temporal effects of the detoxification enzyme inducer, benzyl isothiocyanate: activation of c-Jun N-terminal kinase prior to the transcription factors AP-1 and NFkappaB. PubMed: Chemoprevention of cancer by isothiocyanates, modifiers of carcinogen metabolism. PubMed: Modulation by phytochemicals of cytochrome P450-linked enzyme activity. PubMed: Inhibition of N'-nitrosonornicotine-induced esophageal tumorigenesis by 3-phenylpropyl isothiocyanate. PubMed: Reactions of a glucosinolate breakdown product (benzyl isothiocyanate) with myoglobin. PubMed: Strong promoting activity of phenylethyl isothiocyanate and benzyl isothiocyanate on urinary bladder carcinogenesis in F344 male rats. PubMed: Regulation of rat glutathione S-transferase A5 by cancer chemopreventive agents: mechanisms of inducible resistance to aflatoxin B1. PubMed: The environment of 5S rRNA in the ribosome: cross-links to the GTPase-associated area of 23S rRNA. PubMed: Chemopreventive isothiocyanates induce apoptosis and caspase-3-like protease activity. PubMed: Radioimmunotherapy for breast cancer using indium-111/yttrium-90 BrE-3: results of a phase I clinical trial. PubMed: Approaches to chemoprevention of lung cancer based on carcinogens in tobacco smoke. PubMed: Effects of isothiocyanates on cytochrome P-450 1A1 and 1A2 activity and on the mutagenicity of heterocyclic amines. PubMed: Enzyme induction and comparative oxidative desulfuration of isothiocyanates to isocyanates. PubMed: Inhibition of N-nitrosodimethylamine demethylase in rat and human liver microsomes by isothiocyanates and their glutathione, L-cysteine, and N-acetyl-L-cysteine conjugates. PubMed: Lack of inhibitory effect of benzyl isothiocyanate on 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP)-induced mammary carcinogenesis in rats. PubMed: Influence of benzylisothiocyanate and 13-cis-retinoic acid on micronucleus formation induced by benzo[a]pyrene. PubMed: Aberrant crypts as a biomarker for colon cancer: evaluation of potential chemopreventive agents in the rat. PubMed: Chemoprevention of lung cancer by isothiocyanates. PubMed: In vitro and in vivo antitumor activity of benzyl isothiocyanate: a natural product from Tropaeolum majus. PubMed: Effect of alkyl chain length on inhibition of N-nitrosomethylbenzylamine-induced esophageal tumorigenesis and DNA methylation by isothiocyanates. PubMed: Forward and reverse catalysis and product sequestration by human glutathione S-transferases in the reaction of GSH with dietary aralkyl isothiocyanates. PubMed: Selective toxicity of compounds naturally present in food toward the transformed phenotype of human colorectal cell line HT29. PubMed: Some aspects of reactions of benzyl isothiocyanate with bovine sarcoplasmic proteins. PubMed: Chemoprevention by isothiocyanates. PubMed: Cytotoxic and clastogenic effects of benzyl isothiocyanate towards cultured mammalian cells. PubMed: Lung tumor induction in A/J mice by the tobacco smoke carcinogens 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and benzo[a]pyrene: a potentially useful model for evaluation of chemopreventive agents. PubMed: Isolation and structure elucidation of new nitrile and mustard oil glycosides from Moringa oleifera and their effect on blood pressure. PubMed: Inhibitory effects of benzyl thiocyanate and benzyl isothiocyanate on methylazoxymethanol acetate-induced intestinal carcinogenesis in rats. PubMed: Effects of isothiocyanate alkyl chain-length on hamster liver cytochrome P-450 activity. PubMed: Effects of isothiocyanates on the metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and benzo[a]pyrene by hamster and rat liver microsomes. PubMed: Effects of isothiocyanates on tumorigenesis by benzo[a]pyrene in murine tumor models. PubMed: Inhibitory effects of benzyl isothiocyanate and benzyl thiocyanate on diethylnitrosamine-induced hepatocarcinogenesis in rats. PubMed: Radioimmunolocalization of metastatic breast carcinoma using indium-111-methyl benzyl DTPA BrE-3 monoclonal antibody: phase I study. PubMed: The clastogenic effects of isothiocyanates. PubMed: Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice. PubMed: Modulation of carcinogen-induced polyoma DNA-replication by organoselenium and organosulfur chemopreventive agents. PubMed: Modifying effects of benzyl isothiocyanate and benzyl thiocyanate on DNA synthesis in primary cultures of rat hepatocytes. PubMed: Reversed-phase high-performance liquid chromatographic separation of the stereoisomers of labetalol via derivatization with chiral and non-chiral isothiocyanate reagents. PubMed: In vitro stability of EDTA and DTPA immunoconjugates of monoclonal antibody 2G3 labeled with indium-111. PubMed: Structure-function relationships in indium-111 radioimmunoconjugates. PubMed: Subacute oral toxicity study of benzyl isothiocyanate in rats. PubMed: Hepatobiliary delivery of polyaminopolycarboxylate chelates: synthesis and characterization of a cholic acid conjugate of EDTA and biodistribution and imaging studies with its indium-111 chelate. PubMed: Characterization of antibody-chelator conjugates: determination of chelator content by terbium fluorescence titration. PubMed: Inhibition of tobacco-specific nitrosamine 4-(N-nitrosomethylamino)-1-(3-pyridyl)-1-butanone (NNK) tumorigenesis with aromatic isothiocyanates. PubMed: Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in mouse lung microsomes and its inhibition by isothiocyanates. PubMed: Inhibition of carcinogenesis by minor anutrient constituents of the diet. PubMed: Effect of dietary aromatic isothiocyanates fed subsequent to the administration of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone on lung tumorigenicity in mice. PubMed: Inhibition of tobacco-specific nitrosamine 4-(methyl-nitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung tumors and DNA methylation in F344 rats and A/J mice by phenethyl isothiocyanate. PubMed: Inhibition of carcinogenesis by naturally-occurring and synthetic compounds. PubMed: Ethylene-like activity of isocyanides. PubMed: Effects of alkyl chain length on the inhibition of NNK-induced lung neoplasia in A/J mice by arylalkyl isothiocyanates. PubMed: Effects of aromatic isothiocyanates on tumorigenicity, O6-methylguanine formation, and metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mouse lung. PubMed: Induction of glutathione S-transferase, placental type in T9 glioma cells by dibutyryladenosine 3',5'-cyclic monophosphate and modification of its expression by naturally occurring isothiocyanates. PubMed: Reversed-phase liquid chromatographic separation of enantiomeric and diastereomeric bases related to chloramphenicol and thiamphenicol. PubMed: Characterization of benzyl isothiocyanate and phenyl acetonitrile from papayas by mass spectrometry. PubMed: Detoxification of isothiocyanate allelochemicals by glutathione transferase in three lepidopterous species. PubMed: Studies on the metabolism and excretion of benzyl isothiocyanate in man. PubMed: Differential induction of rat hepatic glutathione S-transferase isoenzymes by hexachlorobenzene and benzyl isothiocyanate. Comparison with induction by phenobarbital and 3-methylcholanthrene. PubMed: Inhibitory effects of benzyl isothiocyanate administered shortly before diethylnitrosamine or benzo[a]pyrene on pulmonary and forestomach neoplasia in A/J mice. PubMed: Cytomorphological changes in liver cells exposed to allyl and benzyl isothiocyanate and their cysteine and glutathione conjugates. PubMed: Glutathione- and cysteine-mediated cytotoxicity of allyl and benzyl isothiocyanate. PubMed: Induction of DT-diaphorase by anticarcinogenic sulfur compounds in mice. PubMed: Effects of disulfiram, diethyldithiocarbamate, bisethylxanthogen, and benzyl isothiocyanate on glutathione transferase activities in mouse organs. PubMed: Investigations into the possible regulation of negative gravitropic curvature in intact Avena sativa plants and in isolated stem segments by ethylene and gibberellins. PubMed: Antiasthmatic effects of onion extracts--detection of benzyl- and other isothiocyanates (mustard oils) as antiasthmatic compounds of plant origin. PubMed: Effects of dietary compounds on alpha-hydroxylation of N-nitrosopyrrolidine and N'-nitrosonornicotine in rat target tissues. PubMed: Quantitation of a bioactive metabolite in undisturbed rhizosphere-Benzyl isothiocyanate fromCarica papaya L. PubMed: Postharvest Variation in Cell Wall-Degrading Enzymes of Papaya (Carica papaya L.) during Fruit Ripening. PubMed: The metabolism of benzyl isothiocyanate and its cysteine conjugate in guinea-pigs and rabbits. PubMed: Enhancement of glutathione S-transferase activity of the esophagus by phenols, lactones, and benzyl isothiocyanate. PubMed: Glutathione S-transferase activity: enhancement by compounds inhibiting chemical carcinogenesis and by dietary constituents. PubMed: Inhibition of carcinogen-induced neoplasia by sodium cyanate, tert-butyl isocyanate, and benzyl isothiocyanate administered subsequent to carcinogen exposure. PubMed: Enhancement of glutathione S-transferase activity of the mouse forestomach by inhibitors of Benzo[a]pyrene-induced neoplasia of the forestomach. PubMed: Inhibition of carcinogenic effects of polycyclic hydrocarbons by benzyl isothiocyanate and related compounds. PubMed: The metabolism of benzyl isothiocyanate and its cysteine conjugate. PubMed: Inhibition of papain by isothiocyanates. PubMed: Inhibition of ethylene evolution in papaya pulp tissue by benzyl isothiocyanate. PubMed: Bacterial degradation of benzyl isothiocyanate. PubMed: Control of encephalitis in laboratory monkeys by benzyl isothiocyanate.