Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H9NS |
| Molecular Weight | 163.239 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
S=C=NCCC1=CC=CC=C1
InChI
InChIKey=IZJDOKYDEWTZSO-UHFFFAOYSA-N
InChI=1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2
| Molecular Formula | C9H9NS |
| Molecular Weight | 163.239 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
Phenethyl isothiocyanate (PEITC) presents in cruciferous vegetables which have been shown to decrease the risk of various types of malignancies. PEITC targets multiple proteins to suppress various cancer-promoting mechanisms such as cell proliferation, progression and metastasis. PEITC induces apoptosis in human colon cancer HT-29 cells, prostate cancer cells, and osteogenic sarcoma U-2 OS cells. Unique to prostate cancer is that PEITC downregulates the transcriptional factor Sp1, a regulator of AR expression. PEITC suppresses 4-(methylnitrosamino)-1-(3-pyridyl)-1-butoneinduced pulmonary neoplasia in A/J mouse lung, exhibits cancer chemopreventive activity in rat and reduces azoxymethane-induced colonic aberrant crypt foci formation. PEITC appears to be a promising agent for cancer therapy and is already under clinical trials for leukemia and lung cancer.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparison of growth inhibition profiles and mechanisms of apoptosis induction in human colon cancer cell lines by isothiocyanates and indoles from Brassicaceae. | 2006-07-25 |
|
| In vitro and in vivo anti-inflammatory activity of a seed preparation containing phenethylisothiocyanate. | 2006-04 |
|
| Effects of benzyl and phenethyl isothiocyanate on P450s 2A6 and 2A13: potential for chemoprevention in smokers. | 2006-04 |
|
| Inhibition of EGFR signaling in human prostate cancer PC-3 cells by combination treatment with beta-phenylethyl isothiocyanate and curcumin. | 2006-03 |
|
| ERK and JNK signaling pathways are involved in the regulation of activator protein 1 and cell death elicited by three isothiocyanates in human prostate cancer PC-3 cells. | 2006-03 |
|
| Effects of indole-3-carbinol and phenethyl isothiocyanate on colon carcinogenesis induced by azoxymethane in rats. | 2006-02 |
|
| Combined inhibitory effects of curcumin and phenethyl isothiocyanate on the growth of human PC-3 prostate xenografts in immunodeficient mice. | 2006-01-15 |
|
| Current trends and perspectives in nutrition and cancer prevention. | 2006 |
|
| Modulation of apoptosis by cancer chemopreventive agents. | 2005-12-11 |
|
| Modulation of multigene expression and proteome profiles by chemopreventive agents. | 2005-12-11 |
|
| The time-dependent effect of gluconasturtiin and phenethyl isothiocyanate on metabolic and antioxidative parameters in rats. | 2005-12 |
|
| Acute and subacute effects of tobacco alkaloids, tobacco-specific nitrosamines and phenethyl isothiocyanate on N'-nitrosonornicotine metabolism in rats. | 2005-11-15 |
|
| Biofumigation: environmental impacts on the biological activity of diverse pure and plant-derived isothiocyanates. | 2005-11 |
|
| Membrane transport of dietary phenethyl isothiocyanate by ABCG2 (breast cancer resistance protein). | 2005-10-04 |
|
| Pharmacokinetics of dietary phenethyl isothiocyanate in rats. | 2005-10 |
|
| Phenethyl isothiocyanate and sulforaphane and their N-acetylcysteine conjugates inhibit malignant progression of lung adenomas induced by tobacco carcinogens in A/J mice. | 2005-09-15 |
|
| N-acetylcysteine conjugate of phenethyl isothiocyanate enhances apoptosis in growth-stimulated human lung cells. | 2005-09-15 |
|
| Chemoprevention of acrylamide toxicity by antioxidative agents in rats--effective suppression of testicular toxicity by phenylethyl isothiocyanate. | 2005-09 |
|
| Effects of antioxidants and caspase-3 inhibitor on the phenylethyl isothiocyanate-induced apoptotic signaling pathways in human PLC/PRF/5 cells. | 2005-08-22 |
|
| Transport of dietary phenethyl isothiocyanate is mediated by multidrug resistance protein 2 but not P-glycoprotein. | 2005-08-15 |
|
| Hydrogen sulfide protects colon cancer cells from chemopreventative agent beta-phenylethyl isothiocyanate induced apoptosis. | 2005-07-14 |
|
| Induction of glutathione S-transferase and glutathione by toxic compounds and elicitors in reed canary grass. | 2005-07 |
|
| Role of mitogen-activated protein kinases in phenethyl isothiocyanate-induced apoptosis in human prostate cancer cells. | 2005-07 |
|
| Suppression of NF-kappaB and NF-kappaB-regulated gene expression by sulforaphane and PEITC through IkappaBalpha, IKK pathway in human prostate cancer PC-3 cells. | 2005-06-30 |
|
| Beta-phenylethyl and 8-methylsulphinyloctyl isothiocyanates, constituents of watercress, suppress LPS induced production of nitric oxide and prostaglandin E2 in RAW 264.7 macrophages. | 2005-06 |
|
| Caspase-dependent apoptosis induction by phenethyl isothiocyanate, a cruciferous vegetable-derived cancer chemopreventive agent, is mediated by Bak and Bax. | 2005-04-01 |
|
| Comparison of phenethyl and 6-phenylhexyl isothiocyanate-induced toxicity in rat esophageal cell lines with and without glutathione depletion. | 2005-03-15 |
|
| Limited tumor-initiating activity of phenylethyl isothiocyanate by promotion with sodium L-ascorbate in a rat two-stage urinary bladder carcinogenesis model. | 2005-03-10 |
|
| Induction of phase I, II and III drug metabolism/transport by xenobiotics. | 2005-03 |
|
| beta-Phenylethyl isothiocyanate mediated apoptosis: a proteomic investigation of early apoptotic protein changes. | 2005-03 |
|
| Beta-phenylethyl isothiocyanate mediated apoptosis; contribution of Bax and the mitochondrial death pathway. | 2005-01 |
|
| Animal models and analytical approaches for understanding the relationships between wine and cancer. | 2005 |
|
| Effect of organic isothiocyanates on breast cancer resistance protein (ABCG2)-mediated transport. | 2004-12 |
|
| Involvement of cytochrome P450 2E1 in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse model of Parkinson's disease. | 2004-10 |
|
| Induction of apoptosis in a non-small cell human lung cancer cell line by isothiocyanates is associated with P53 and P21. | 2004-10 |
|
| Dietary organic isothiocyanates are cytotoxic in human breast cancer MCF-7 and mammary epithelial MCF-12A cell lines. | 2004-09 |
|
| Ingestion of an isothiocyanate metabolite from cruciferous vegetables inhibits growth of human prostate cancer cell xenografts by apoptosis and cell cycle arrest. | 2004-08 |
|
| Phytochemical-induced changes in gene expression of carcinogen-metabolizing enzymes in cultured human primary hepatocytes. | 2004-07 |
|
| Effects of benzyl-, phenethyl-, and alpha-naphthyl isothiocyanates on P-glycoprotein- and MRP1-mediated transport. | 2004-07 |
|
| Potent chemopreventive agents against pancreatic cancer. | 2004-06 |
|
| Effects of dietary anticarcinogens and nonsteroidal anti-inflammatory drugs on rat gastrointestinal UDP-glucuronosyltransferases. | 2004-05-27 |
|
| Proteasome-mediated degradation of cell division cycle 25C and cyclin-dependent kinase 1 in phenethyl isothiocyanate-induced G2-M-phase cell cycle arrest in PC-3 human prostate cancer cells. | 2004-05 |
|
| The chemopreventive agent phenethyl isothiocyanate sensitizes cells to Fas-mediated apoptosis. | 2004-05 |
|
| Intrinsic cytotoxicity and chemomodulatory actions of novel phenethylisothiocyanate sphingoid base derivatives in HL-60 human promyelocytic leukemia cells. | 2004-05 |
|
| Modulatory properties of various natural chemopreventive agents on the activation of NF-kappaB signaling pathway. | 2004-04 |
|
| Modulation of AP-1 by natural chemopreventive compounds in human colon HT-29 cancer cell line. | 2004-04 |
|
| Genetic and metabolic effects of gluconasturtiin, a glucosinolate derived from cruciferae. | 2004-01-12 |
|
| Hydrolysis of glucosinolates to isothiocyanates after ingestion of raw or microwaved cabbage by human volunteers. | 2004-01 |
|
| Inhibition by allyl sulfides and phenethyl isothiocyanate of methyl-n-pentylnitrosamine depentylation by rat esophageal microsomes, human and rat CYP2E1, and Rat CYP2A3. | 2004 |
|
| Effect of dietary constituents with chemopreventive potential on adduct formation of a low dose of the heterocyclic amines PhIP and IQ and phase II hepatic enzymes. | 2003 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:59:28 GMT 2025
by
admin
on
Mon Mar 31 17:59:28 GMT 2025
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| Record UNII |
6U7TFK75KV
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| Record Status |
Validated (UNII)
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| Record Version |
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Download
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Systematic Name | English | ||
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Code | English | ||
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Code | English |
| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C45711
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NCI_THESAURUS |
C54630
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JECFA EVALUATION |
PHENETHYL ISOTHIOCYANATE
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| Code System | Code | Type | Description | ||
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DB12695
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351346
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PHENETHYL ISOTHIOCYANATE
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218-855-5
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DTXSID5021120
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C058305
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C2233
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87868
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m8610
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PRIMARY | Merck Index | ||
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1554
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6U7TFK75KV
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2257-09-2
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16741
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