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

Molecular Formula	C8H7NS
Molecular Weight	149.213
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Benzyl isothiocyanate inhibits murine WEHI-3 leukemia cells in vitro and promotes phagocytosis in BALB/c mice in vivo.	2009-11	19250670
Cancer preventive isothiocyanates induce selective degradation of cellular alpha- and beta-tubulins by proteasomes.	2009-06-19	19339240
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.	2009-06-15	19303893
The antimicrobial effects of glucosinolates and their respective enzymatic hydrolysis products on bacteria isolated from the human intestinal tract.	2009-06	19291240
Potency of isothiocyanates to induce luciferase reporter gene expression via the electrophile-responsive element from murine glutathione S-transferase Ya.	2009-06	19232536
Degradation and sorption of 2-propenyl and benzyl isothiocyanate in soil.	2009-06	19191470
Activation of ATM/Chk1 by curcumin causes cell cycle arrest and apoptosis in human pancreatic cancer cells.	2009-05-05	19401701
The role of STAT-3 in the induction of apoptosis in pancreatic cancer cells by benzyl isothiocyanate.	2009-02-04	19176463
Isothiocyanate profile and selective antibacterial activity of root, stem, and leaf extracts derived from Raphanus sativus L.	2009-02-03	19182965
Aurintricarboxylic acid inhibits influenza virus neuraminidase.	2009-02	19014974
Isothiocyanates repress estrogen receptor alpha expression in breast cancer cells.	2009-01	19082460
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
Inhibitory effect of fermented papaya preparation on hydroxyl radical generation from methylguanidine.	2008-11	19015753
(-)-Epigallocatechin-3-gallate potentiates the cytotoxicity induced by benzyl isothiocyanate and hydrogen peroxide in human Jurkat T lymphocytes.	2008-11	18997418
Benzyl isothiocyanate targets mitochondrial respiratory chain to trigger reactive oxygen species-dependent apoptosis in human breast cancer cells.	2008-10-31	18768478
Benzylglucosinolate, benzylisothiocyanate, and myrosinase activity in papaya fruit during development and ripening.	2008-10-22	18826320
Coordinate regulation of enzyme markers for inflammation and for protection against oxidants and electrophiles.	2008-10-14	18838692
Triphala inhibits both in vitro and in vivo xenograft growth of pancreatic tumor cells by inducing apoptosis.	2008-10-10	18847491
Dietary isothiocyanate mediated apoptosis of human cancer cells is associated with Bcl-xL phosphorylation.	2008-10	18813778
ATP depletion alters the mode of cell death induced by benzyl isothiocyanate.	2008-10	18675902
Suppressive Effects of Selected Food Phytochemicals on CD74 Expression in NCI-N87 Gastric Carcinoma Cells.	2008-09	18818744
Cancer is a preventable disease that requires major lifestyle changes.	2008-09	18626751
Broccoli consumption interacts with GSTM1 to perturb oncogenic signalling pathways in the prostate.	2008-07-02	18596959
Benzyl isothiocyanate inhibits metalloproteinase-2/-9 expression by suppressing the mitogen-activated protein kinase in SK-Hep1 human hepatoma cells.	2008-07	18502015
Etoposide induces ATM-dependent mitochondrial biogenesis through AMPK activation.	2008-04-23	18431490
Herbal compounds and toxins modulating TRP channels.	2008-03	19305789
Binding to protein by isothiocyanates: a potential mechanism for apoptosis induction in human non small lung cancer cells.	2008	19003576
Glutathione- and thioredoxin-related enzymes are modulated by sulfur-containing chemopreventive agents.	2007-10	17937621
Modifying effects of dietary factors on (-)-epigallocatechin-3-gallate-induced pro-matrix metalloproteinase-7 production in HT-29 human colorectal cancer cells.	2007-10	17928719
Formation and degradation kinetics of the biofumigant benzyl isothiocyanate in soil.	2007-06-15	17626424
Papaya seed represents a rich source of biologically active isothiocyanate.	2007-05-30	17469845
Selective cytotoxicity of benzyl isothiocyanate in the proliferating fibroblastoid cells.	2007-02-01	17096346
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
p38MAPK mediates benzyl isothiocyanate-induced p21WAF1 expression in vascular smooth muscle cells via the regulation of Sp1.	2006-11-24	17026958
Benzyl isothiocyanate-induced apoptosis in human breast cancer cells is initiated by reactive oxygen species and regulated by Bax and Bak.	2006-11	17121941
Protective effects of benzyl isothiocyanate and sulforaphane but not resveratrol against initiation of pancreatic carcinogenesis in hamsters.	2006-09-28	16386831
Characterization of two Arabidopsis thaliana glutathione S-transferases.	2006-09	16538523
Newly constructed stable reporter cell lines for mechanistic studies on electrophile-responsive element-mediated gene expression reveal a role for flavonoid planarity.	2006-07-14	16756964
Haplotype-environment interactions that regulate the human glutathione S-transferase P1 promoter.	2006-06-15	16778223
Invasive plant suppresses the growth of native tree seedlings by disrupting belowground mutualisms.	2006-05	16623597
Raphanus sativus and its isothiocyanates inhibit vascular smooth muscle cells proliferation and induce G(1) cell cycle arrest.	2006-05	16546717
Effects of benzyl and phenethyl isothiocyanate on P450s 2A6 and 2A13: potential for chemoprevention in smokers.	2006-04	16364922
Effect of isothiocyanates on nuclear accumulation of NF-kappaB, Nrf2, and thioredoxin in caco-2 cells.	2006-03-08	16506816
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.	2006-03	16520658
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
Dietary isothiocyanates modify mitochondrial functions through their electrophilic reaction.	2005-12	16377906
Modulation of jejunal contractions by extract of Carica papaya L. seeds.	2005-07	16161026

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:15:11 GMT 2025` Edited by `admin` on `Mon Mar 31 19:15:11 GMT 2025`
Record UNII	871J6YOR8Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZYLISOTHIOCYANATE

Preferred Name

English

BENZYL ISOTHIOCYANATE

Systematic Name

English

ISOTHIOCYANATOMETHYL)BENZENE

Common Name

English

TROMACAPS

Common Name

English

Benzylisothiocyanate [WHO-DD]

Common 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