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Phenethyl isothiocyanate

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Phenethyl isothiocyanate Basic information

Product Name:
Phenethyl isothiocyanate
Synonyms:
  • 2-Phenylethyl isothiocyanate, Phenethyl isothiocyanate
  • β-Phenylethyl isothiocyanate, Phenethyl isothiocyanate
  • Isothiocyanic acid phenethyl
  • PHENETHYL GLUCOSINOLATE POTASSIUM SALT(GLUCONASTURTIIN)(RG)
  • Isothiocyanic Acid 2-Phenylethyl Ester Phenethyl Isothiocyanate
  • PHENYLETHYL ISOTHIOCYANATE(P)(REQUEST QUOTE)
  • Phenethyl isothiocyanate 99%
  • 2-Phenylethyl Isothiocyanate, 97.0%(GC)
CAS:
2257-09-2
MF:
C9H9NS
MW:
163.24
EINECS:
218-855-5
Product Categories:
  • Aromatics Compounds
  • Aromatics
  • Sulfur & Selenium Compounds
Mol File:
2257-09-2.mol
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Phenethyl isothiocyanate Chemical Properties

Melting point:
143~145℃
Boiling point:
75 °C0.25 mm Hg
Density 
1.094 g/mL at 25 °C(lit.)
FEMA 
4014 | PHENETHYL ISOTHIOCYANATE
refractive index 
n20/D 1.5888(lit.)
Flash point:
>230 °F
storage temp. 
Refrigerator, Under Inert Atmosphere
form 
Liquid
color 
Clear colorless to yellow
Specific Gravity
1.09
Water Solubility 
insoluble
Sensitive 
Moisture Sensitive
JECFA Number
1563
Merck 
14,7226
BRN 
2084162
InChIKey
IZJDOKYDEWTZSO-UHFFFAOYSA-N
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)
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Safety Information

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
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)

MSDS

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Phenethyl isothiocyanate Usage And Synthesis

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

Phenethyl isothiocyanate has a strong green irritating odor.

Chemical Properties

Light Yellow Liquid

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.

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.

Preparation

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

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).

Phenethyl isothiocyanateSupplier

Manac (SHANGHAI) TRADING CO., LTD Gold
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