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Phenethyl isothiocyanate

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Phenethyl isothiocyanate
Names
Preferred IUPAC name (2-Isothiocyanatoethyl)benzene
Other names Phenylethyl isothiocyanate; Phenethyl mustard oil
Identifiers
CAS Number
3D model (JSmol)
Abbreviations PEITC
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.017.142 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2Key: IZJDOKYDEWTZSO-UHFFFAOYSA-N
  • InChI=1/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2Key: IZJDOKYDEWTZSO-UHFFFAOYAB
SMILES
  • S=C=N/CCc1ccccc1
Properties
Chemical formula C9H9NS
Molar mass 163.24 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Phenethyl isothiocyanate (PEITC) is a naturally occurring isothiocyanate whose precursor, gluconasturtiin is found in some cruciferous vegetables, especially watercress.

PEITC has been studied for its potential for chemoprevention of cancers, such as prostate cancer.

In terms of biosynthesis, PEITC is produced from gluconasturtiin by the action of the enzyme myrosinase.

References

  1. "Dictionary of Cancer Terms: PEITC". National Cancer Institute.
  2. Cheung, KL; Kong, AN (2010). "Molecular targets of dietary phenethyl isothiocyanate and sulforaphane for cancer chemoprevention". The AAPS Journal. 12 (1): 87–97. doi:10.1208/s12248-009-9162-8. PMC 2811646. PMID 20013083.
  3. Kwon, Ki Han; Xu, Changjiang; Keum, Young-Sam; Khor, Tin Oo; Kim, Jung-Hwan; Huang, Mou-Tuan; Reddy, Bandaru S.; Li, Wenge; Kong, Ah-Ng Tony (2007). "Natural dietary phytochemicals: a promising future for cancer prevention and treatment of earlier lesion". Cancer: Disease Progression and Chemoprevention: 109–126.
  4. Wang, LG; Chiao, JW (2010). "Prostate cancer chemopreventive activity of phenethyl isothiocyanate through epigenetic regulation (review)". International Journal of Oncology. 37 (3): 533–9. doi:10.3892/ijo_00000702. PMID 20664922.
Cruciferous biochemistry
Types of compounds
Glucosinolates
Isothiocyanates (ITC, mustard oils)
Bioactive metabolites
Categories: