Benzyl isothiocyanate

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Benzyl isothiocyanate
Benzyl isothiocyanate.svg
Benzyl isothiocyanate-3D-balls-by-AHRLS-2012.png
Benzyl isothiocyanate-3D-vdW-by-AHRLS-2012.png
Names
IUPAC name
(Isothiocyanatomethyl)benzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.777
Properties
C8H7NS
Molar mass 149.21 g·mol−1
Density 1.125 g/mL[1]
Boiling point 242-243 [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Benzyl isothiocyanate (BITC) is an isothiocyanate found in plants of the mustard family.

Occurrence[edit]

It can be found in Alliaria petiolata, pilu oil, and papaya seeds[2] where it is the main product of the Glucotropaeolin breakdown by the enzyme myrosinase.

Activity[edit]

Benzyl isothiocyanate, and other isothiocynates in general, were found to be protective against pancreatic carcinogenesis in vitro[3] via expression of p21/WAF1 gene.[4] A recent published study showed its impact on obesity, fatty liver, and insulin resistance in diet-induced obesity mouse model. [5]

References[edit]

  1. ^ a b "Benzyl isothiocyanate". Sigma-Aldrich.
  2. ^ Nakamura, Yoshimasa; Yoshimoto, Motoko; Murata, Yoshiyuki; Shimoishi, Yasuaki; Asai, Yumi; Park, Eun Young; Sato, Kenji; Nakamura, Yasushi (2007). "Papaya Seed Represents a Rich Source of Biologically Active Isothiocyanate". Journal of Agricultural and Food Chemistry. 55 (11): 4407. doi:10.1021/jf070159w. PMID 17469845.
  3. ^ Kuroiwa, Yuichi; Nishikawa, Akiyoshi; Kitamura, Yasuki; Kanki, Keita; Ishii, Yuji; Umemura, Takashi; Hirose, Masao (2006). "Protective effects of benzyl isothiocyanate and sulforaphane but not resveratrol against initiation of pancreatic carcinogenesis in hamsters". Cancer Letters. 241 (2): 275. doi:10.1016/j.canlet.2005.10.028. PMID 16386831.
  4. ^ Moon, Sung-Kwon; Choi, Yung-Hyun; Kim, Cheorl-Ho; Choi, Won-Seok (2006). "P38MAPK mediates benzyl isothiocyanate-induced p21WAF1 expression in vascular smooth muscle cells via the regulation of Sp1". Biochemical and Biophysical Research Communications. 350 (3): 662. doi:10.1016/j.bbrc.2006.09.092. PMID 17026958.
  5. ^ Alsanea, Sary; Liu, Dexi (November 2017). "BITC and S-Carvone Restrain High-Fat Diet-Induced Obesity and Ameliorate Hepatic Steatosis and Insulin Resistance". Pharmaceutical Research. 34 (11): 2241–2249. doi:10.1007/s11095-017-2230-3. ISSN 1573-904X. PMC 5757875. PMID 28733781.