2257-09-2 Usage
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
Different sources of media describe the Chemical Properties of 2257-09-2 differently. You can refer to the following data:
1. Phenethyl isothiocyanate has a strong green irritating odor.
2. Light Yellow Liquid
Uses
Different sources of media describe the Uses of 2257-09-2 differently. You can refer to the following data:
1. 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.
2. Phenethyl isothiocyanate is an 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).
Check Digit Verification of cas no
The CAS Registry Mumber 2257-09-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,2,5 and 7 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 2257-09:
(6*2)+(5*2)+(4*5)+(3*7)+(2*0)+(1*9)=72
72 % 10 = 2
So 2257-09-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NS/c1-8(10-7-11)9-5-3-2-4-6-9/h2-6,8H,1H3
2257-09-2Relevant articles and documents
Novel synthetic aromatic thiourea derivatives and investigations on their cytotoxic potential efficacy
Ray, Ujjayinee,John, Franklin,Pooppadi, Sayeesh,George, Jinu,Sharma, Shivangi,Raghavan, Sathees C
, p. 40 - 47 (2020/09/21)
Aromatic thiourea derivatives were synthesized by standard reactions from isothiocyanates in high yield. An efficient one-pot synthesis of primary amine with carbon disulfide involving the intermediate dithiocarbamate conversion using T3P (propane phosphonic anhydride) to isothiocyanate is reported. Newly synthesized compounds showed excellent luminescence property. Cytotoxic investigation with different human cancer cell lines showed IC50 values varying from of 17 to 40 μM for N-phenethyl-3,4-dihydroisoquinoline-2(1H)-carbothioamide (SCR172) among other molecules. Increase in Sub G1 population and increased depolarisation of mitochondria were evident in cells treated with SCR172, suggesting its role as a cancer therapeutic agent. This provides a lead structure for further synthetic modifications.
Preparation method of phenethyl isothiocyanate
-
Paragraph 0048-0063, (2020/01/25)
The invention relates to a preparation method of phenethyl isothiocyanate. The preparation method of phenylethyl isothiocyanate takes phenylethylamine and carbon disulfide as raw materials and triethylamine as a base to firstly generate dithiocarbamates, and then uses p-toluenesulfonyl chloride to carry out desulfurization to obtain the phenylethyl isothiocyanate. Compared with the prior art, thesynthesis method uses cheaper raw materials which are easy to transport, has high safety, has relatively mild reaction conditions and high reaction yield, therefore, the method solves the problems oflow conversion rate, low boiling point of desulfurizer, large toxicity, extremely unsafe transportation, high product cost and the like existing in the prior art.
