BENZYL ISOTHIOCYANATE

Description

Benzyl isothiocyanate is a natural product found in the Eastern Hemisphere mustard plant?Alliaria petiolata, seeds of the pilu tree (Salvadora persica), and papaya (Carica papaya) seeds. It is a colorless to pale yellow liquid with a boiling point of 242–243 oC and a characteristic watercress-like odor.
In 2006, there was a?report?that isothiocyanates, including benzyl isothiocyanate, protected against pancreatic carcinogenesis in vitro. Based on this study and others, Bo Yu and colleagues at the Chinese Academy of Sciences (including its university) sought to find biosynthetic methods for producing isothiocyanates.
As reported in?ACS Synthetic Biology, the researchers metabolically engineered?Escherichia coli?to synthesize benzyl isothiocyanate. By using a combination of gene mining, pathway engineering, and protein modification, they were able to adapt two enzymes that allowed?E. coli?to make the product.
The authors state that they “provided a proof of concept for the production of benzyl isothiocyanate by microbially produced enzymes and, importantly, laid the groundwork for further metabolic engineering of microbial cells for the production of isothiocyanates.”

Chemical properties

clear yellow liquid

Chemical properties

Pale yellowish liquid; strong, penetrating aroma.

Occurrence

Reported found in common cress, Lepidium sativum, nasturtium, and Tropaeolum majus.

The Uses of BENZYL ISOTHIOCYANATE

A novel medical application of isothiocyanate ester in treating various leukemia, with low toxicity, which includes benzyl isothiocyanate, phenylethyl isothiocyanate, allyl isothiocyanate, sulforaphane, and erucin. Benzyl isothiocyanate (BITC) inhibits the growth of human pancreatic cancer cells by inducing apoptosis.

The Uses of BENZYL ISOTHIOCYANATE

antineoplastic, antibacterial, antifungal

The Uses of BENZYL ISOTHIOCYANATE

Benzyl isothiocyanate has been used in the preparation of S-(N-benzylthiocarbamoyl)-L-glutathione and S-(N-benzylthiocarbamoyl)-L-cysteine.

What are the applications of Application

Benzyl isothiocyanate is an inhibitor of methylazoxymethanol acetate

Definition

ChEBI: Benzyl isothiocyanate is an isothiocyanate and a member of benzenes. It has a role as an antibacterial drug.

Preparation

Benzyl isothiocyanate is synthesized by the following two methods: I) from Benzylamine via Thiuramdisulfide via Sodiumsalt with Iodine to Benzyl-isothiocyanate. 2) from Benzylamine and Thiocarbonyl chloride.

Aroma threshold values

Medium strength odor, watercress type; recommend smelling in a 1.0% solution or less.

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 7021, 1992 DOI: 10.1016/S0040-4039(00)60922-X

General Description

Benzyl isothiocyanate is a naturally-occurring constituent of cruciferous vegetables. It has antibacterial properties and its metabolism in man has been investigated. It inhibits chemically induced cancer in animal models.

Hazard

Very irritant to tissues.

Biochem/physiol Actions

Odor at 1.0%: Vegetative cabbage and radishlike, green with a musty sulfurous earthiness reminiscent of mustard greens.Taste at 0.5ppm: Green vegetative cabbage, kimchi, radish and wasabi-like with green leafy nuances and imparting a strong trigeminal tongue numbing and raspy sensation.

Safety Profile

Poison by intraperitoneal andsubcutaneous routes. Intensely irritating. Mutation datareported. Moderate fire hazard via heat, flame, andoxidizers. To fight fire, use water, spray, foam, drychemical. When heated to decomposition it emits verytoxic NOx

Solubility in organics

Soluble in alcohol and oils.