Benzyl isothiocyanate
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| Names | |||
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| Preferred IUPAC name
(Isothiocyanatomethyl)benzene | |||
| Identifiers | |||
3D model (JSmol)
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| ChemSpider | |||
| ECHA InfoCard | 100.009.777 | ||
PubChem CID
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| UNII | |||
CompTox Dashboard (EPA)
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| 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).
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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 isothiocyanates in general, were found to be protective against pancreatic carcinogenesis in vitro[3] via expression of the p21/WAF1 gene.[4] A recent published study showed its restraining impact on obesity, fatty liver, and insulin resistance in diet-induced obesity mouse model.[5]
References
[edit]- ^ a b "Benzyl isothiocyanate". Sigma-Aldrich.
- ^ 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): 4407–13. doi:10.1021/jf070159w. PMID 17469845.
- ^ 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): 275–80. doi:10.1016/j.canlet.2005.10.028. PMID 16386831.
- ^ 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): 662–8. doi:10.1016/j.bbrc.2006.09.092. PMID 17026958.
- ^ 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.
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