BENZYL ISOTHIOCYANATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H7NS
Molecular Weight	149.213
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

S=C=NCC1=CC=CC=C1

InChI

InChIKey=MDKCFLQDBWCQCV-UHFFFAOYSA-N

InChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Dietary isothiocyanates modify mitochondrial functions through their electrophilic reaction.	2005 Dec	16377906
Modulation of jejunal contractions by extract of Carica papaya L. seeds.	2005 Jul	16161026
Benzyl isothiocyanate (BITC) induces apoptosis in ovarian cancer cells in vitro.	2006	17024969
Cell death induction by isothiocyanates and their underlying molecular mechanisms.	2006	16823098
Effects of benzyl and phenethyl isothiocyanate on P450s 2A6 and 2A13: potential for chemoprevention in smokers.	2006 Apr	16364922
Newly constructed stable reporter cell lines for mechanistic studies on electrophile-responsive element-mediated gene expression reveal a role for flavonoid planarity.	2006 Jul 14	16756964
Haplotype-environment interactions that regulate the human glutathione S-transferase P1 promoter.	2006 Jun 15	16778223
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.	2006 Mar	16520658
Effect of isothiocyanates on nuclear accumulation of NF-kappaB, Nrf2, and thioredoxin in caco-2 cells.	2006 Mar 8	16506816
Invasive plant suppresses the growth of native tree seedlings by disrupting belowground mutualisms.	2006 May	16623597
Raphanus sativus and its isothiocyanates inhibit vascular smooth muscle cells proliferation and induce G(1) cell cycle arrest.	2006 May	16546717
Benzyl isothiocyanate-induced apoptosis in human breast cancer cells is initiated by reactive oxygen species and regulated by Bax and Bak.	2006 Nov	17121941
p38MAPK mediates benzyl isothiocyanate-induced p21WAF1 expression in vascular smooth muscle cells via the regulation of Sp1.	2006 Nov 24	17026958
Characterization of two Arabidopsis thaliana glutathione S-transferases.	2006 Sep	16538523
Protective effects of benzyl isothiocyanate and sulforaphane but not resveratrol against initiation of pancreatic carcinogenesis in hamsters.	2006 Sep 28	16386831
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.	2007	17552357
Lipid peroxidation, oxidative stress genes and dietary factors in breast cancer protection: a hypothesis.	2007	17224037
Selective cytotoxicity of benzyl isothiocyanate in the proliferating fibroblastoid cells.	2007 Feb 1	17096346
Formation and degradation kinetics of the biofumigant benzyl isothiocyanate in soil.	2007 Jun 15	17626424
Papaya seed represents a rich source of biologically active isothiocyanate.	2007 May 30	17469845
Glutathione- and thioredoxin-related enzymes are modulated by sulfur-containing chemopreventive agents.	2007 Oct	17937621
Modifying effects of dietary factors on (-)-epigallocatechin-3-gallate-induced pro-matrix metalloproteinase-7 production in HT-29 human colorectal cancer cells.	2007 Oct	17928719
Binding to protein by isothiocyanates: a potential mechanism for apoptosis induction in human non small lung cancer cells.	2008	19003576
Etoposide induces ATM-dependent mitochondrial biogenesis through AMPK activation.	2008 Apr 23	18431490
Benzyl isothiocyanate inhibits metalloproteinase-2/-9 expression by suppressing the mitogen-activated protein kinase in SK-Hep1 human hepatoma cells.	2008 Jul	18502015
Broccoli consumption interacts with GSTM1 to perturb oncogenic signalling pathways in the prostate.	2008 Jul 2	18596959
Herbal compounds and toxins modulating TRP channels.	2008 Mar	19305789
Inhibitory effect of fermented papaya preparation on hydroxyl radical generation from methylguanidine.	2008 Nov	19015753
(-)-Epigallocatechin-3-gallate potentiates the cytotoxicity induced by benzyl isothiocyanate and hydrogen peroxide in human Jurkat T lymphocytes.	2008 Nov	18997418
Dietary isothiocyanate mediated apoptosis of human cancer cells is associated with Bcl-xL phosphorylation.	2008 Oct	18813778
ATP depletion alters the mode of cell death induced by benzyl isothiocyanate.	2008 Oct	18675902
Triphala inhibits both in vitro and in vivo xenograft growth of pancreatic tumor cells by inducing apoptosis.	2008 Oct 10	18847491
Coordinate regulation of enzyme markers for inflammation and for protection against oxidants and electrophiles.	2008 Oct 14	18838692
Benzylglucosinolate, benzylisothiocyanate, and myrosinase activity in papaya fruit during development and ripening.	2008 Oct 22	18826320
Benzyl isothiocyanate targets mitochondrial respiratory chain to trigger reactive oxygen species-dependent apoptosis in human breast cancer cells.	2008 Oct 31	18768478
Suppressive Effects of Selected Food Phytochemicals on CD74 Expression in NCI-N87 Gastric Carcinoma Cells.	2008 Sep	18818744
Cancer is a preventable disease that requires major lifestyle changes.	2008 Sep	18626751
Phytochemical induction of cell cycle arrest by glutathione oxidation and reversal by N-acetylcysteine in human colon carcinoma cells.	2009	19373606
Enzyme activities and subcellular localization of members of the Arabidopsis glutathione transferase superfamily.	2009	19174456
Aurintricarboxylic acid inhibits influenza virus neuraminidase.	2009 Feb	19014974
The role of STAT-3 in the induction of apoptosis in pancreatic cancer cells by benzyl isothiocyanate.	2009 Feb 4	19176463
Isothiocyanates repress estrogen receptor alpha expression in breast cancer cells.	2009 Jan	19082460
Isothiocyanate profile and selective antibacterial activity of root, stem, and leaf extracts derived from Raphanus sativus L.	2009 Jan-Feb	19182965
The antimicrobial effects of glucosinolates and their respective enzymatic hydrolysis products on bacteria isolated from the human intestinal tract.	2009 Jun	19291240
Potency of isothiocyanates to induce luciferase reporter gene expression via the electrophile-responsive element from murine glutathione S-transferase Ya.	2009 Jun	19232536
Degradation and sorption of 2-propenyl and benzyl isothiocyanate in soil.	2009 Jun	19191470
Transcription factor Nrf2 mediates an adaptive response to sulforaphane that protects fibroblasts in vitro against the cytotoxic effects of electrophiles, peroxides and redox-cycling agents.	2009 Jun 15	19303893
Cancer preventive isothiocyanates induce selective degradation of cellular alpha- and beta-tubulins by proteasomes.	2009 Jun 19	19339240
Activation of ATM/Chk1 by curcumin causes cell cycle arrest and apoptosis in human pancreatic cancer cells.	2009 May 5	19401701
Benzyl isothiocyanate inhibits murine WEHI-3 leukemia cells in vitro and promotes phagocytosis in BALB/c mice in vivo.	2009 Nov	19250670

Patents

Name

Type

Language

BENZYL ISOTHIOCYANATE

Systematic Name

English

ISOTHIOCYANATOMETHYL)BENZENE

Common Name

English

TROMACAPS

Common Name

English

Benzylisothiocyanate [WHO-DD]

Common Name

English

BENZYLISOTHIOCYANATE

Systematic Name

English

BENZYL ISOTHIOCYANATE [MART.]

Common Name

English

TROMALYT

Common Name

English

1-(ISOTHIOCYANATOMETHYL)BENZENE

Systematic Name

English

BENZYL ISOTHIOCYANATE [FHFI]

Common Name

English

NSC-118976

Code

English

FEMA NO. 4428

Code

English

BENZENE, (ISOTHIOCYANATOMETHYL)-

Systematic Name

English

UROGRAN

Common Name

English

ISOTHIOCYANIC ACID, BENZYL ESTER

Common Name

English

BENZYL MUSTARD OIL

Common Name

English

PHENYLMETHYL ISOTHIOCYANATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45711