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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.
Isothiocyanates can be prepared by treating organic dithiocarbamate salts with lead nitrate or tosyl chloride. [5] [6] Synthesis of phenyl isothiocyanate. Isothiocyanates may also be accessed by the fragmentation reactions of 1,4,2-oxathiazoles. [7] This methodology has been applied to a polymer-supported synthesis of isothiocyanates. [8]
By contrast, N=C and C=S distances are 117 and 158 pm in isothiocyanates. [7] Typical bond angles for C−S−C are 100°. [3] By contrast C−N=C in aryl isothiocyanates is 165°. Again, the thiocyanate isomers are quite different with C−S−C angle near 100°. In both organic thiocyanate and isothiocyanate isomers the SCN angle approaches ...
Glucotropaeolin or benzyl glucosinolate is a glucosinolate found in cruciferous vegetables, particularly garden cress. [1] Upon enzymatic activity, it is transformed into benzyl isothiocyanate , which contributes to the characteristic flavor of these brassicas .
The isothiocyanate further decomposes into hydroxybenzyl alcohols with the release of thiocyanates. [1] [2] [3] In the presence of a nitrile-specifier protein, the less toxic 4-hydroxyphenylacetonitrile is formed from the mustard oil glycoside instead. The cabbage butterfly exploits this mechanism to avoid the toxic effects of the ...
Isocyanates are electrophiles, and as such they are reactive toward a variety of nucleophiles including alcohols, amines, and even water having a higher reactivity compared to structurally analogous isothiocyanates. [11] Upon treatment with an alcohol, an isocyanate forms a urethane linkage: ROH + R'NCO → ROC(O)N(H)R'
Hard metal cations, as classified by HSAB theory, tend to form N-bonded complexes (isothiocyanates), whereas class B or soft metal cations tend to form S-bonded thiocyanate complexes. For the isothiocyanates, the M-N-C angle is usually close to 180°. For the thiocyanates, the M-S-C angle is usually close to 100°.
Isothiocyanates are conventionally written as two words. [4] The following are some glucosinolates and their isothiocyanate products: [4] Allylglucosinolate is the precursor of allyl isothiocyanate; Benzylglucosinolate (glucotropaeolin) is the precursor of benzyl isothiocyanate