Benzyl isothiocyanate

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Benzyl isothiocyanate

Names

Preferred IUPAC name

(Isothiocyanatomethyl)benzene

Identifiers

CAS Number

622-78-6^Y

3D model (JSmol)

Interactive image

ChemSpider

2256

ECHA InfoCard

100.009.777

PubChem CID

2346

UNII

871J6YOR8Q^Y

CompTox Dashboard (EPA)

DTXSID0020155

InChI

InChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2
Key: MDKCFLQDBWCQCV-UHFFFAOYSA-N

SMILES

c1ccc(cc1)CN=C=S

Properties

C₈H₇NS

149.21 g·mol⁻¹

1.125 g/mL^[1]

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 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.

v t e Cruciferous biochemistry
Types of compounds	Phenylthiocarbamide (PTC/PTU) Thiocyanates Nitriles Indoles Gibberellin
Glucosinolates	Glucobrassicin Glucocapparin Glucoraphanin Gluconasturtiin Glucotropaeolin Progoitrin Sinigrin Sinalbin
Isothiocyanates (ITC, mustard oils)	Sulforaphane (SFN) Raphanin Allyl isothiocyanate (AITC) Methyl isothiocyanate (MITC) Benzyl isothiocyanate (BITC) Fluorescein isothiocyanate (FITC) Phenyl isothiocyanate (PITC) Phenethyl isothiocyanate (PEITC) 6-MITC Erucin
Bioactive metabolites	Goitrin Indole-3-carbinol
Brassicaceae (Cruciferous vegetables): Brassica Cruciferous Biochemistry genera (list)

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