- Thermal Degradation of Allyl Isothiocyanate in Aqueous Solution
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Allyl isothiocyanate in an aqueous solution was heated and refluxed at 100 °C for 1 h. The reaction mixtures were then extracted with methylene chloride and analyzed using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The mixtures in aqueous phase were analyzed by high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC-MS) equipped with an atmospheric-pressure chemical ionization (APCI) interface. The compounds identified in the methylene chloride extracts included diallyl sulfide, diallyl disulfide, diallyl trisulfide, diallyl tetrasulfide, allyl thiocyanate, 3H-1,2-dithiolene, 2-vinyl-4H-1,3-dithiin, 4H-1,2,3-trithiin, and 5-methyl-1,2,3,4-tetrathiane. N,N′-Diallylthiourea, which was the major degradation product in the aqueous phase from the thermal reaction of allyl isothiocyanate, was identified by using LC-MS (APCI+), direct-probe EI-MS, and 1H-NMR. The possible mechanism for the formation of these products was proposed.
- Chen, Chung-Wen,Ho, Chi-Tang
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p. 220 - 223
(2007/10/03)
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- Oxidative Scission of the Disulfide Bond of Cystine and Polypeptides by the Action of Allyl Isothiocyanate
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The interaction of allyl isothiocyanate (1) with L-cystine and polypeptides under mild conditions was studied in detail.The reaction mixtures composed of isothiocyanate and cystine were incubated at 40, 60 and 80 deg C, in which cystine completely decomposed after 120, 6 and 2 hr, respectively.Degradation products were isolated and identified as 2-allylamino-2-thiazoline-4-carboxylic acid (2), 2-amino-2-thiazoline-4-carboxylic acid (3) and 3(3H)-allyl-5,6-dihydro-5-amino-2(2H)-thioxo-1,3-thiazin-4-one (4).These products were formed through an oxidative acission of the disulfide bond in cystine by the electrophilic attack of allyl isothiocyanate; the products 2 and 4 seemed to be derived through alanyl N-allyldithiocarbamate and the product 3 through β-thiocyanoalanine.In addition, it was confirmed that a part of the disulfide bond in oxidized glutathione and insulin was also cleaved by isothiocyanate.
- Kawakishi, Shunro,Goto, Tamami,Namiki, Mitsuo
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p. 2071 - 2076
(2007/10/02)
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