Phenethyl isothiocyanate

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Phenethyl isothiocyanate
Phenethyl isothiocyanate.svg
Phenethyl isothiocyanate-3D-balls-by-AHRLS-2012.png
Phenethyl isothiocyanate-3D-vdW-by-AHRLS-2012.png
Names
Preferred IUPAC name
(2-Isothiocyanatoethyl)benzene
Other names
Phenylethyl isothiocyanate; Phenethyl mustard oil
Identifiers
3D model (JSmol)
AbbreviationsPEITC
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.017.142 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2 Yes check.svgY
    Key: IZJDOKYDEWTZSO-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2
    Key: IZJDOKYDEWTZSO-UHFFFAOYAB
  • S=C=N/CCc1ccccc1
Properties
C9H9NS
Molar mass 163.24 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Phenethyl isothiocyanate (PEITC) is a naturally occurring isothiocyanate whose precursor, gluconasturtiin is found in some cruciferous vegetables, [1] especially watercress.

PEITC has been studied for its potential for chemoprevention of cancers, [2] [3] such as prostate cancer. [4]

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

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Glucosinolates are natural components of many pungent plants such as mustard, cabbage, and horseradish. The pungency of those plants is due to mustard oils produced from glucosinolates when the plant material is chewed, cut, or otherwise damaged. These natural chemicals most likely contribute to plant defence against pests and diseases, and impart a characteristic bitter flavor property to cruciferous vegetables.

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<span class="mw-page-title-main">Gluconasturtiin</span> Chemical compound

Gluconasturtiin or phenethyl glucosinolate is one of the most widely distributed glucosinolates in the cruciferous vegetables, mainly in the roots, and is probably one of the plant compounds responsible for the natural pest-inhibiting properties of growing crucifers, such as cabbage, mustard or rape, in rotation with other crops. This effect of gluconasturtiin is due to its degradation by the plant enzyme myrosinase into phenethyl isothiocyanate, which is toxic to many organisms.

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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.