377430

Sigma-Aldrich

Allyl isothiocyanate

contains BHT as stabilizer, 95%

Synonym(s):
AITC, Oil of mustard
Linear Formula:
CH2=CHCH2NCS
CAS Number:
Molecular Weight:
99.15
Beilstein/REAXYS Number:
773748
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

contains

BHT as stabilizer

refractive index

n20/D 1.529 (lit.)

bp

150 °C (lit.)

mp

−80 °C (lit.)

density

1.013 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C=CCN=C=S

InChI

1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2

InChI key

ZOJBYZNEUISWFT-UHFFFAOYSA-N

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Application

Allyl isothiocyanate (AITC) was suitable for use in the following studies:
  • Quantitation of the N-acetylcysteine conjugate of AITC in human urine after ingestion of mustard.
  • Evaluation of the fungitoxic activity of AITC vapour on Penicillium expansum on pears, particularly on a thiabendazole (TBZ)-resistant P. expansum strain in vivo, to verify whether AITC treatment could be a substitute for TBZ.
  • Study of the induction of acetylation of histone in mouse erythroleukemia cells by some organosulfur compounds.

Packaging

5, 100, 500 g in glass bottle

Biochem/physiol Actions

Naturally occurring constituent of cruciferous vegetables that has anti-tumor and anti-oxidant properties. Induces the activity of phase II detoxification enzymes in the urinary bladder and, thus, may be chemoprotective against bladder cancer.

Signal Word

Danger

hazcat

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - Skin Sens. 1

storage_class_code

3 - Flammable liquids

WGK Germany

WGK 3

Flash Point(F)

113.0 °F - closed cup

Flash Point(C)

45 °C - closed cup

Certificate of Analysis

Certificate of Origin

Chang Liu et al.
Neuron, 109(2), 273-284 (2020-11-06)
The TRPA1 ion channel is activated by electrophilic compounds through the covalent modification of intracellular cysteine residues. How non-covalent agonists activate the channel and whether covalent and non-covalent agonists elicit the same physiological responses are not understood. Here, we report...
Antifungal vapour-phase activity of allyl-isothiocyanate against Penicillium expansum on pears.
Mari M, et al.
Plant Pathology, 51(2), 231-236 (2002)
Ying Li et al.
Journal of colloid and interface science, 438, 130-137 (2014-12-03)
Allyl isothiocyanate (AITC), an organosulfur compound in cruciferous vegetables, is a natural antimicrobial and potential chemopreventive agent. However, the instability of AITC in aqueous systems restrains its applications. In this study, oil-in-water AITC nanoemulsion was prepared by the emulsion inversion...
Francielle de Vargas Pinheiro et al.
European journal of pharmacology, 747, 105-113 (2014-12-17)
Sympathetic fibres maintain some forms of neuropathic pain, but the underlying mechanisms are poorly understood. Therefore, this study investigated the possible involvement of transient receptor potential ankyrin 1 (TRPA1) and the role of the sympathetic nervous system (involved in sympathetically...
Jill M Recla et al.
Pain, 160(8), 1740-1753 (2019-07-25)
Identification of genetic variants that influence susceptibility to pain is key to identifying molecular mechanisms and targets for effective and safe therapeutic alternatives to opioids. To identify genes and variants associated with persistent pain, we measured late-phase response to formalin...

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