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Details

Stereochemistry ACHIRAL
Molecular Formula C4H5NS
Molecular Weight 99.154
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ALLYL ISOTHIOCYANATE

SMILES

C=CCN=C=S

InChI

InChIKey=ZOJBYZNEUISWFT-UHFFFAOYSA-N
InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2

HIDE SMILES / InChI

Molecular Formula C4H5NS
Molecular Weight 99.154
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Allyl isothiocyanate (AITC), also known as mustard oil, is one of the most common naturally occurring isothiocyanates, which occurs in many common cruciferous vegetables. Besides antimicrobial activity against a wide spectrum of pathogens, it showed anticancer activity in both cultured cancer cells and animal models, although the underlining mechanisms remain largely undefined. Allyl isothiocyanate is a TRPA1 and TRPV1 agonist and pungency and lachrymatory effects of Allyl isothiocyanate are mediated through the TRPA1 and TRPV1 ion channels. Allyl isothiocyanate irritates the mucous membranes and induces eczematous or vesicular skin reactions.

Approval Year

Doses

Doses

DosePopulationAdverse events​
0.05 % 1 times / day single, topical
Studied dose
Dose: 0.05 %, 1 times / day
Route: topical
Route: single
Dose: 0.05 %, 1 times / day
Sources:
healthy, 38 years
Health Status: healthy
Age Group: 38 years
Sex: F
Sources:
Other AEs: Contact dermatitis...
Other AEs:
Contact dermatitis
Sources:
0.1 % 1 times / day single, topical
Studied dose
Dose: 0.1 %, 1 times / day
Route: topical
Route: single
Dose: 0.1 %, 1 times / day
Sources:
healthy, 61 years
Health Status: healthy
Age Group: 61 years
Sex: M
Sources:
Other AEs: Contact dermatitis...
Other AEs:
Contact dermatitis
Sources:
AEs

AEs

AESignificanceDosePopulation
Contact dermatitis
0.05 % 1 times / day single, topical
Studied dose
Dose: 0.05 %, 1 times / day
Route: topical
Route: single
Dose: 0.05 %, 1 times / day
Sources:
healthy, 38 years
Health Status: healthy
Age Group: 38 years
Sex: F
Sources:
Contact dermatitis
0.1 % 1 times / day single, topical
Studied dose
Dose: 0.1 %, 1 times / day
Route: topical
Route: single
Dose: 0.1 %, 1 times / day
Sources:
healthy, 61 years
Health Status: healthy
Age Group: 61 years
Sex: M
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Characterization of spinal alpha-adrenergic modulation of nociceptive transmission and hyperalgesia throughout postnatal development in rats.
2007-08
Influence of cabbage processing methods and prebiotic manipulation of colonic microflora on glucosinolate breakdown in man.
2007-08
MAK-4 and -5 supplemented diet inhibits liver carcinogenesis in mice.
2007-06-08
Novel agonistic action of mustard oil on recombinant and endogenous porcine transient receptor potential V1 (pTRPV1) channels.
2007-05-15
Methyl p-hydroxybenzoate causes pain sensation through activation of TRPA1 channels.
2007-05
Activation of TRPA1 channels by the fatty acid amide hydrolase inhibitor 3'-carbamoylbiphenyl-3-yl cyclohexylcarbamate (URB597).
2007-05
Effects of allyl isothiocyanate from horseradish on several experimental gastric lesions in rats.
2007-04-30
Activation of TRPA1 channel facilitates excitatory synaptic transmission in substantia gelatinosa neurons of the adult rat spinal cord.
2007-04-18
TRPA1 is differentially modulated by the amphipathic molecules trinitrophenol and chlorpromazine.
2007-03-09
TRP channels as target sites for insecticides: physiology, pharmacology and toxicology.
2007-03
Allyl isothiocyanate (AITC) and phenyl isothiocyanate (PITC) inhibit tumour-specific angiogenesis by downregulating nitric oxide (NO) and tumour necrosis factor-alpha (TNF-alpha) production.
2007-03
Primary and secondary hyperalgesia can be differentiated by postnatal age and ERK activation in the spinal dorsal horn of the rat pup.
2007-03
Combined effect of volatile antimicrobial agents on the growth of Penicillium notatum.
2007-02-15
Active spice-derived components can inhibit inflammatory responses of adipose tissue in obesity by suppressing inflammatory actions of macrophages and release of monocyte chemoattractant protein-1 from adipocytes.
2007-02-13
Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines.
2007-02-01
Influence of local treatments with capsaicin or allyl isothiocyanate in the sensitization phase of a fluorescein-isothiocyanate-induced contact sensitivity model.
2007
Protective effects of isothiocyanates towards N-nitrosamine-induced DNA damage in the single-cell gel electrophoresis (SCGE)/HepG2 assay.
2006-11-03
Changes in glucosinolate concentrations, myrosinase activity, and production of metabolites of glucosinolates in cabbage (Brassica oleracea Var. capitata) cooked for different durations.
2006-10-04
Active packaging of cheese with allyl isothiocyanate, an alternative to modified atmosphere packaging.
2006-10
Fumigant activity of plant essential oils and components from horseradish (Armoracia rusticana), anise (Pimpinella anisum) and garlic (Allium sativum) oils against Lycoriella ingenua (Diptera: Sciaridae).
2006-08
Protective effects of isothiocyanates towards N-nitrosamine-induced DNA damage in the single-cell gel electrophoresis (SCGE)/HepG2 assay.
2006-07-28
Phenethyl isothiocyanate triggers apoptosis in Jurkat cells made resistant by the overexpression of Bcl-2.
2006-07-01
[Studies on chemical components of essential oil of crude semen sinapis and roasted semen sinapis].
2006-07
Contractile mechanisms coupled to TRPA1 receptor activation in rat urinary bladder.
2006-06-28
Impaired nociception and inflammatory pain sensation in mice lacking the prokineticin receptor PKR1: focus on interaction between PKR1 and the capsaicin receptor TRPV1 in pain behavior.
2006-06-21
Radioprotective activity of naturally occurring organosulfur compounds.
2006-05-27
Invasive plant suppresses the growth of native tree seedlings by disrupting belowground mutualisms.
2006-05
Oregano, thyme and clove-derived flavors and skin sensitizers activate specific TRP channels.
2006-05
Sensitivity to allyl isothiocyanate, dimethyl trisulfide, sinigrin, and cooked cauliflower consumption.
2006-05
Inhibitory effects of microencapsulated allyl isothiocyanate (AIT) against Escherichia coli O157:H7 in refrigerated, nitrogen packed, finely chopped beef.
2006-04-01
Allyl isothiocyanate and its N-acetylcysteine conjugate suppress metastasis via inhibition of invasion, migration, and matrix metalloproteinase-2/-9 activities in SK-Hep 1 human hepatoma cells.
2006-04
Modest induction of phase 2 enzyme activity in the F-344 rat prostate.
2006-03-15
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.
2006-03
Molecular identification and functional characterization of a temperature-sensitive transient receptor potential channel (TRPM8) from canine.
2006-01-13
Management of root knot nematodes in turfgrass using mustard formulations and biostimulants.
2006
Induction of quinone reductase by allylisothiocyanate (AITC) and the N-acetylcysteine conjugate of AITC in Hepa1c1c7 mouse hepatoma cells.
2006
Pheromonal activity of compounds identified from male Phyllotreta cruciferae: field tests of racemic mixtures, pure enantiomers, and combinations with allyl isothiocyanate.
2005-11
Biofumigation: environmental impacts on the biological activity of diverse pure and plant-derived isothiocyanates.
2005-11
The role of c-Jun in the AP-1 activation induced by naturally occurring isothiocyanates.
2005-09
Responses of flea beetle Phyllotreta cruciferae to synthetic aggregation pheromone components and host plant volatiles in field trials.
2005-08
Trigeminal sensitization and desensitization in the nasal cavity: a study of cross interactions.
2005-06
Ambient odors influence the amplitude and time course of visual distraction.
2005-06
Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro.
2005-05-18
How cold is it? TRPM8 and TRPA1 in the molecular logic of cold sensation.
2005-04-22
Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing.
2005-04-20
Inactivation of Escherichia coli O157:H7 in packaged ground beef by allyl isothiocyanate.
2005-04-01
Use of mustard flour to inactivate Escherichia coli O157:H7 in ground beef under nitrogen flushed packaging.
2005-04-01
Characterization of antimutagenic mechanism of 3-allyl-5-substituted 2-thiohydantoins against 2-amino-3-methylimidazo[4,5-f]quinoline.
2005-04
Differential expression and stability of endogenous nuclear factor E2-related factor 2 (Nrf2) by natural chemopreventive compounds in HepG2 human hepatoma cells.
2005-03-31
Biofumigant compounds released by field pennycress (Thlaspi arvense) seedmeal.
2005-01
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:35:11 GMT 2025
Edited
by admin
on Mon Mar 31 17:35:11 GMT 2025
Record UNII
BN34FX42G3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FEMA NO. 2034
Preferred Name English
ALLYL ISOTHIOCYANATE
FCC   FHFI   HSDB   MART.   MI   USAN   USP  
USAN  
Official Name English
ALLYL ISOTHIOCYANATE [MART.]
Common Name English
ALLYL ISOTHIOCYANATE [IARC]
Common Name English
NSC-5572
Code English
ALLYL ISOTHIOCYANATE [USAN]
Common Name English
ALLYL ISOTHIOCYANATE [USP MONOGRAPH]
Common Name English
1-PROPENE, 3-ISOTHIOCYANATO-
Systematic Name English
ALLYL ISOTHIOCYANATE [FHFI]
Common Name English
ALLYL ISOTHIOCYANATE [FCC]
Common Name English
ALLYL ISOTHIOCYANATE, STABILIZED
Common Name English
ALLYL ISOTHIOCYANATE [HSDB]
Common Name English
Isothiocyanic acid allyl ester
Systematic Name English
Allyl isothiocyanate [WHO-DD]
Common Name English
ALLYL ISOTHIOCYANATE [MI]
Common Name English
ARTIFICIAL MUSTARD OIL
Common Name English
Classification Tree Code System Code
JECFA EVALUATION ALLYL ISOTHIOCYANATE
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
CFR 21 CFR 172.515
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
IARC Allyl isothiocyanate
EPA PESTICIDE CODE 4901
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
NCI_THESAURUS C45711
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
Code System Code Type Description
WIKIPEDIA
ALLYL ISOTHIOCYANATE
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
NSC
5572
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
HSDB
617
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
FDA UNII
BN34FX42G3
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
CHEBI
73224
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
MESH
C004471
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
ChEMBL
CHEMBL233248
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
PUBCHEM
5971
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
MERCK INDEX
m1556
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY Merck Index
SMS_ID
300000001589
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
GRAS Notification (GRN No.)
180
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
EPA CompTox
DTXSID3020047
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
JECFA MONOGRAPH
1551
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-309-2
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
NCI_THESAURUS
C68556
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
ALANWOOD
allyl isothiocyanate
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
CAS
57-06-7
Created by admin on Mon Mar 31 17:35:11 GMT 2025 , Edited by admin on Mon Mar 31 17:35:11 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY