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Benzyl isothiocyanate

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

Benzyl isothiocyanate
Names
Preferred IUPAC name
(Isothiocyanatomethyl)benzene
Identifiers
  • 622-78-6 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2256
ECHA InfoCard 100.009.777
  • 2346
UNII
  • 871J6YOR8Q Y
  • DTXSID0020155
  • InChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2
    Key: MDKCFLQDBWCQCV-UHFFFAOYSA-N
  • c1ccc(cc1)CN=C=S
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).

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

  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): 4407–13. 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): 275–80. 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): 662–8. 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.

benzyl, isothiocyanate, bitc, isothiocyanate, found, plants, mustard, family, namespreferred, iupac, name, isothiocyanatomethyl, benzeneidentifierscas, number, model, jsmol, interactive, imagechemspider, 2256echa, infocard, 777pubchem, 2346unii, 871j6yor8q, yc. Benzyl isothiocyanate BITC is an isothiocyanate found in plants of the mustard family Benzyl isothiocyanate NamesPreferred IUPAC name Isothiocyanatomethyl benzeneIdentifiersCAS Number 622 78 6 Y3D model JSmol Interactive imageChemSpider 2256ECHA InfoCard 100 009 777PubChem CID 2346UNII 871J6YOR8Q YCompTox Dashboard EPA DTXSID0020155InChI InChI 1S C8H7NS c10 7 9 6 8 4 2 1 3 5 8 h1 5H 6H2Key MDKCFLQDBWCQCV UHFFFAOYSA NSMILES c1ccc cc1 CN C SPropertiesChemical formula C 8H 7N SMolar mass 149 21 g mol 1Density 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 referencesOccurrence editIt 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 editBenzyl 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 nbsp This article about an organic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Benzyl isothiocyanate amp oldid 1099993275, wikipedia, wiki, book, books, library,

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