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HomeProduct name listPhenethyl isothiocyanate

Phenethyl isothiocyanate

Synonym(s):2-Phenylethyl isothiocyanate;PEITC;Phenethyl isothiocyanate

  • CAS NO.:2257-09-2
  • Empirical Formula: C9H9NS
  • Molecular Weight: 163.24
  • MDL number: MFCD00004821
  • EINECS: 218-855-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-31 20:01:59
Phenethyl isothiocyanate Structural

What is Phenethyl isothiocyanate?

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.

The Uses of Phenethyl isothiocyanate

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.

The Uses of Phenethyl isothiocyanate

Phenethyl isothiocyanate is an NNK-induced lung tumorigenesis inhibitor.

What are the applications of Application

Phenethyl isothiocyanate is a NNK-induced lung tumorigenesis inhibitor

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.

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).

Properties of Phenethyl isothiocyanate

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
Water Solubility  insoluble
Sensitive  Moisture Sensitive
Merck  14,7226
JECFA Number 1563
BRN  2084162
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 information for Phenethyl isothiocyanate

Signal word Danger
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H315:Skin corrosion/irritation
H317:Sensitisation, Skin
H319:Serious eye damage/eye irritation
H334:Sensitisation, respiratory
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Phenethyl isothiocyanate

InChIKey IZJDOKYDEWTZSO-UHFFFAOYSA-N

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