Phenylethyl isothiocyanate

Names

[ Name ]:
Phenylethyl isothiocyanate

[Synonym ]:
PhCH2CH2NCS
Phenylethyl isothiocyanate
2-Phenylethyl Isothiocyanate
EINECS 218-855-5
PEITC
Isothiocyanic Acid 2-Phenylethyl Ester
Phenylaethylsenfoel
Phenethyl mustard oil
MFCD00004821
Phenethyl Isothiocyanate
2-phenylethyl-ITC
2-isothiocyanatoethylbenzene

Biological Activity

[Description]:

2-Phenylethyl isothiocyanate is a potent antifungal agent. 2-Phenylethyl isothiocyanate significantly inhibited spore germination and mycelial growth of Alternaria alternata, with a MIC (minimum inhibitory concentration) of 1.22 mM. The antifungal effect of 2-Phenylethyl isothiocyanate against Alternaria alternata might be via reduction in toxin content and breakdown of cell membrane integrity[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

[References]

[1]. B. J. Smith, et al. In vitro inhibition of soil microorganisms by 2-phenylethyl isothiocyanate. Plant Pathology. 4 October 2002;51(5):585-593.

[2]. Zhang M, et al. 2-Phenylethyl Isothiocyanate Exerts Antifungal Activity against Alternaria alternata by Affecting Membrane Integrity and Mycotoxin Production. Toxins (Basel). 2020 Feb 15;12(2):124.

Chemical & Physical Properties

[ Density]:
1.094 g/mL at 25 °C(lit.)

[ Boiling Point ]:
75 °C0.25 mm Hg

[ Molecular Formula ]:
C₉H₉NS

[ Molecular Weight ]:
163.23900

[ Flash Point ]:
>230 °F

[ Exact Mass ]:
163.04600

[ PSA ]:
44.45000

[ LogP ]:
2.33190

[ Vapour Pressure ]:
0.0427mmHg at 25°C

[ Index of Refraction ]:
n20/D 1.5888(lit.)

[ Water Solubility ]:
insoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NX9115000

CHEMICAL NAME :: Isothiocyanic acid, phenethyl ester

CAS REGISTRY NUMBER :: 2257-09-2

BEILSTEIN REFERENCE NO. :: 2084162

LAST UPDATED :: 199701

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C9-H9-N-S

MOLECULAR WEIGHT :: 163.25

WISWESSER LINE NOTATION :: SCN2R

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 :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 700 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 :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 50 mg/kg

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

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 + H332-H315-H317-H319-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 ]:
S23-S26-S36-S36/37

[ RIDADR ]:
UN 2206 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
NX9115000

[ Packaging Group ]:
III

[ Hazard Class ]:
8

[ HS Code ]:
2930909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Phenethyl isothiocyanate, a naturally occurring phytochemical, is an antagonist of the aryl hydrocarbon receptor.

Mol. Nutr. Food. Res. 56(3) , 425-34, (2012)

The aryl hydrocarbon (Ah) receptor is a ligand-activated transcription factor that is activated by many carcinogens, and its target gene products play a major role in tumour development, so that antag...

Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).

J. Med. Chem. 51 , 3275-87, (2008)

The chemical space of registered oral drugs was explored for inhibitors of the human multidrug-resistance associated protein 2 (MRP2; ABCC2), using a data set of 191 structurally diverse drugs and dru...

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...

Related Compounds

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