Phenethyl isothiocyanate Property

Melting point:

143～145℃

Boiling point:

75 °C0.25 mm Hg

Density 

1.094 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.5888(lit.)

FEMA 

4014 | PHENETHYL ISOTHIOCYANATE

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml

form 

Liquid

color 

Clear colorless to yellow

Specific Gravity

1.09

Odor

at 0.01 % in propylene glycol. green horseradish gooseberry watercress

Odor Type

sulfurous

Water Solubility 

insoluble

Sensitive 

Moisture Sensitive

JECFA Number

1563

Merck 

14,7226

BRN 

2084162

InChIKey

IZJDOKYDEWTZSO-UHFFFAOYSA-N

LogP

3.47

CAS DataBase Reference

2257-09-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, (2-isothiocyanatoethyl)-(2257-09-2)

EPA Substance Registry System

Benzene, (2-isothiocyanatoethyl)- (2257-09-2)

Safety

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-42-42/43

Safety Statements 

23-26-36-36/37

RIDADR 

UN 2206 6.1/PG 3

WGK Germany 

3

RTECS 

NX9115000

F 

10-23

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29309090

Toxicity

LD50 in mice (mg/kg): 700 orally; 150 s.c.; 50 i.v. (Lichtenstein)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Phenethyl isothiocyanate Chemical Properties,Usage,Production

Description

Phenethyl isothiocyanate is a naturally occurring isothiocyanate in cruciferous vegetables. Phenethyl isothiocyanate is a chemopreventive agent. It inhibits cancer cell growth by arresting the cell cycle and inducing apoptosis in various human cancer cell models.

Chemical Properties

Light Yellow Liquid

Chemical Properties

Phenethyl isothiocyanate has a strong green irritating odor.

Uses

Phenethyl isothiocyanate is an NNK-induced lung tumorigenesis inhibitor.

Uses

Flavor ingredient; provides the hot or burning sensation in horseradish.
Phenethyl isothiocyanate (PEITC)，one of the major compounds from dietary cruciferousvegetables，has been found to have antitumor properties and therefore could generate special interest for the development of chemopreventive andor chemotherapeutic agent for human cancers.

Preparation

Prepared by hydrolysis of gluconasturtiin, an abundant natural product present in cruciferous vegetables.

Definition

ChEBI: An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.

General Description

Phenethyl isothiocyanate, an organic isothiocyanate, is a cruciferous vegetable ingredient present as a glucosinolate in cabbage, turnips, radishes, etc. It is a well-known chemopreventive agent reported to be effective against cancers affecting the lung, breast, pancreas, prostate and so on.

Pharmacokinetics

Phenethyl isothiocyanate (PEITC) is one of the most extensively studied members of the isothiocyanate family, found in cruciferous vegetables, such as watercress. It is responsible for anti-cancer activities. In addition, it has shown to inhibit migration and invasion of many types of human cancer cells. PEITC selectively kills cancer cells, but not normal cells. It generates reactive oxygen species (ROS) to trigger signal transduction, leading to cell cycle arrest, autophagy, and/or apoptosis. However, the molecular mechanisms by which PEITC acts as a growth inhibitor and autophagy and/or apoptosis inducer in cancer cells have not been fully investigated. PEITC also is able to activate ERK and JNK signal transduction, which in turn induces expression of stress-responsive genes. Specifically, this agent has been shown to reactivate gene expression of a detoxification enzyme, glutathione S-transferase that is silenced in prostate carcinoma.
Phenethyl Isothiocyanate has been used in trials studying the prevention and treatment of Leukemia, Lung Cancer, Tobacco Use Disorder, and Lymphoproliferative Disorders.

Anticancer Research

PEITC is a naturally occurring isothiocyanate, found mostly in cruciferous vegetablesincluding cauliflower, watercress, cabbage, Brussels sprouts, garden cress, broccoli,and bok choy. It shows chemopreventive and anticancer activity againstmelanoma, breast cancer, myeloma, human liver hepatoma, non-small cell lung cancer,cervical cancer, prostate cancer, and osteogenic sarcoma. It induces apoptosis in some drug resistance cell lines. Its mechanism of action is much diversified in variouscancer cells. It induces apoptosis in highly metastatic human non-small cell lungcancer, L9981 cells via caspase-3 activation, and cell cycle arrest in G2/M phase bymodulation of cyclin B1 expression while targeting MAPK/AP-1 pathway. In cervicalcancer cells, it increases the death receptor (DR4, DR5) expression, cleaves caspase-3, induces caspase-8, truncates BID, and downregulates ERK1/2 and MEKphosphorylation while maintaining the expression of JNK and phospho-p38MAPK. In human prostate cancer (DU 145) cell line, PEITC induces apoptosis byactivating caspase cascade pathway (Wang et al. 2012; Cheung and Kong 2010).