a-Isothiocyanatotoluene

Names

[ CAS No. ]:
622-78-6

[ Name ]:
a-Isothiocyanatotoluene

[Synonym ]:
MFCD00004819
Toluene, α-isothiocyanato-
(Isothiocyanatomethyl)benzene
a-Isothiocyanatotoluene
EINECS 210-753-9
Benzyl isothiocyanate
Benzene, (isothiocyanatomethyl)-

Biological Activity

[Description]:

Benzyl isothiocyanate is a member of natural isothiocyanates with antimicrobial activity[1][2]. Benzyl isothiocyanate potent inhibits cell mobility, migration and invasion nature and matrix metalloproteinase-2 (MMP-2) activity of murine melanoma cells[2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Endocrinology

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Abdel-Kader MS, et al. Quantitative Analysis of Benzyl Isothiocyanate in Salvadora persica Extract and Dental Care Herbal Formulations Using Reversed Phase C18 High-Performance Liquid Chromatography Method. Pharmacogn Mag. 2017 Oct;13(Suppl 3):S412-S416.

[2]. Lai KC, et al. Benzyl isothiocyanate and phenethyl isothiocyanate inhibit murine melanoma B16F10 cell migration and invasion in vitro. Int J Oncol. 2017 Sep;51(3):832-840.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
243.8±9.0 °C at 760 mmHg

[ Melting Point ]:
41 °C

[ Molecular Formula ]:
C₈H₇NS

[ Molecular Weight ]:
149.213

[ Flash Point ]:
100.4±26.5 °C

[ Exact Mass ]:
149.029922

[ PSA ]:
44.45000

[ LogP ]:
3.02

[ Vapour Pressure ]:
0.0±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.560

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NX8250000

CHEMICAL NAME :: Isothiocyanic acid, benzyl ester

CAS REGISTRY NUMBER :: 622-78-6

BEILSTEIN REFERENCE NO. :: 0386135

LAST UPDATED :: 199701

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C8-H7-N-S

MOLECULAR WEIGHT :: 149.22

WISWESSER LINE NOTATION :: SCN1R

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: Mutation test systems - not otherwise specified

MUTATION DATA

TEST SYSTEM :: Mammal - species unspecified

DOSE/DURATION :: 800 ug/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 300,111,1993

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H312-H315-H319-H332-H334-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338-P342 + P311

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S26-S36/37/39

[ RIDADR ]:
2810

[ WGK Germany ]:
3

[ RTECS ]:
NX8250000

[ Packaging Group ]:
III

[ Hazard Class ]:
8

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

In vitro metabolic conversion of the organic breakdown products of glucosinolate to goitrogenic thiocyanate anion.

J. Sci. Food Agric. 95 , 2244-51, (2015)

Glucosinolates are abundant in Brassicaceae vegetables, and they are degraded into various organic breakdown products (BPs) (R-CN, -NCS and -SCN) by myrosinase when plant tissues are damaged. This stu...

Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.

Curr. Drug Metab. 6 , 413-54, (2005)

The inhibition of human cytochrome P450s (CYPs) is one of the most common mechanisms which can lead to drug-drug interactions. The inhibition of CYPs can be reversible (competitive or non-competitive)...

Transient receptor potential ankyrin 1 (TRPA1) channel as emerging target for novel analgesics and anti-inflammatory agents.

J. Med. Chem. 53 , 5085-107, (2010)