Benzyl isothiocyanate

{{Chembox  | ImageFile1 = Benzyl isothiocyanate.svg | ImageSize1 = 150px | ImageFileL2 = Benzyl isothiocyanate-3D-balls-by-AHRLS-2012.png | ImageSizeL2 = 150px | ImageFileR2 = Benzyl isothiocyanate-3D-vdW-by-AHRLS-2012.png | ImageSizeR2 = 150px

| ImageAlt =  | PIN = (Isothiocyanatomethyl)benzene | OtherNames =  | Section1 = {{Chembox Identifiers | CASNo = 622-78-6 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 871J6YOR8Q | PubChem = 2346 | ChemSpiderID = 2256 | SMILES = c1ccc(cc1)CN=C=S | StdInChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2 | StdInChIKey = MDKCFLQDBWCQCV-UHFFFAOYSA-N }} | Section2 = {{Chembox Properties | C=8|H=7|N=1|S=1 | Appearance = | Density = 1.125 g/mL<ref name=Aldrich>{{cite web | url = http://www.sigmaaldrich.com/catalog/product/aldrich/252492?lang=en | publisher = Sigma-Aldrich | title = Benzyl isothiocyanate }}</ref> | MeltingPt = | BoilingPt = 242-243 | BoilingPt_ref = <ref name=Aldrich/> | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

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

==Occurrence== It can be found in ''Alliaria petiolata'', pilu oil, and papaya seeds<ref>{{cite journal | doi = 10.1021/jf070159w| pmid = 17469845| title = Papaya Seed Represents a Rich Source of Biologically Active Isothiocyanate| journal = Journal of Agricultural and Food Chemistry| volume = 55| issue = 11| pages = 4407–13| year = 2007| last1 = Nakamura| first1 = Yoshimasa| last2 = Yoshimoto| first2 = Motoko| last3 = Murata| first3 = Yoshiyuki| last4 = Shimoishi| first4 = Yasuaki| last5 = Asai| first5 = Yumi| last6 = Park| first6 = Eun Young| last7 = Sato| first7 = Kenji| last8 = Nakamura| first8 = Yasushi}}</ref> where it is the main product of the glucotropaeolin breakdown by the enzyme myrosinase.

==Activity== Benzyl isothiocyanate, and other isothiocyanates in general, were found to be protective against pancreatic carcinogenesis ''in vitro''<ref>{{cite journal | doi = 10.1016/j.canlet.2005.10.028| pmid = 16386831| title = Protective effects of benzyl isothiocyanate and sulforaphane but not resveratrol against initiation of pancreatic carcinogenesis in hamsters| journal = Cancer Letters| volume = 241| issue = 2| pages = 275–80| year = 2006| last1 = Kuroiwa| first1 = Yuichi| last2 = Nishikawa| first2 = Akiyoshi| last3 = Kitamura| first3 = Yasuki| last4 = Kanki| first4 = Keita| last5 = Ishii| first5 = Yuji| last6 = Umemura| first6 = Takashi| last7 = Hirose| first7 = Masao}}</ref> via expression of the ''p21/WAF1'' gene.<ref>{{cite journal | doi =10.1016/j.bbrc.2006.09.092| pmid =17026958| title =P38MAPK mediates benzyl isothiocyanate-induced ''p21WAF1'' expression in vascular smooth muscle cells via the regulation of Sp1| journal =Biochemical and Biophysical Research Communications| volume =350| issue =3| pages =662–8| year =2006| last1 =Moon| first1 =Sung-Kwon| last2 =Choi| first2 =Yung-Hyun| last3 =Kim| first3 =Cheorl-Ho| last4 =Choi| first4 =Won-Seok}}</ref> One published study showed its restraining impact on obesity, fatty-liver, and insulin resistance in diet-induced obesity mouse models.<ref>{{Cite journal|last1=Alsanea|first1=Sary|last2=Liu|first2=Dexi|date=November 2017|title=BITC and S-Carvone Restrain High-Fat Diet-Induced Obesity and Ameliorate Hepatic Steatosis and Insulin Resistance|journal=Pharmaceutical Research|volume=34|issue=11|pages=2241–2249|doi=10.1007/s11095-017-2230-3|issn=1573-904X|pmid=28733781|pmc=5757875}}</ref>

==References== {{reflist}}

Category:Isothiocyanates Category:Benzyl esters