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
Preferred IUPAC name
(Isothiocyanatomethyl)benzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.777 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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).

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

Contents

Occurrence

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

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]

Related Research Articles

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Beta cells (β-cells) are a type of cell found in pancreatic islets that synthesize and secrete insulin and amylin. Beta cells make up 50–70% of the cells in human islets. In patients with Type 1 diabetes, beta-cell mass and function are diminished, leading to insufficient insulin secretion and hyperglycemia.

Leptin Hormone that inhibits hunger

Leptin is a hormone predominantly made by adipose cells and enterocytes in the small intestine that helps to regulate energy balance by inhibiting hunger, which in turn diminishes fat storage in adipocytes. Leptin is coded for by the LEP gene. Leptin acts on cell receptors in the arcuate and ventromedial nuclei, as well as other parts of the hypothalamus and dopaminergic neurons of the ventral tegmental area, consequently mediating feeding.

Isothiocyanate Salt or ester of isothiocyanic acid

Isothiocyanate is the chemical group –N=C=S, formed by substituting the oxygen in the isocyanate group with a sulfur. Many natural isothiocyanates from plants are produced by enzymatic conversion of metabolites called glucosinolates. These natural isothiocyanates, such as allyl isothiocyanate, are also known as mustard oils. An artificial isothiocyanate, phenyl isothiocyanate, is used for amino acid sequencing in the Edman degradation.

Adipose tissue Loose connective tissue composed mostly by adipocytes

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Neuropeptide Y Mammalian protein found in Homo sapiens

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Hyperinsulinemia Abnormal increase in insulin in the bloodstream relative to glucose

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Amylin

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Pyruvate carboxylase

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Peptide YY Peptide released from cells in the ileum and colon in response to feeding

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Ursolic acid Pentacyclic chemical compound found in fruits

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Peroxisome proliferator-activated receptor gamma Protein-coding gene in the species Homo sapiens

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LCMT2

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Chemerin Protein-coding gene in the species Homo sapiens

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Forkhead box protein O1 Protein

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References

  1. 1 2 "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.