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https://hdl.handle.net/2440/23926
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Type: | Journal article |
Title: | 4,4'-Dihydroxy-3,3',5,5'-tetramethoxyazodioxybenzene: an unexpected dimer formed during hydroxylamine extractions of wheat flour |
Author: | Asenstorfer, R. Mares, D. |
Citation: | Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2006; 62(39):9289-9293 |
Publisher: | Pergamon-Elsevier Science Ltd |
Issue Date: | 2006 |
ISSN: | 0040-4020 |
Abstract: | Neutral hydroxylamine extracts of wheat contained a product that was colourless at pH<5 (λ max 340 nm) and yellow at pH>9 (λ max 400 nm). ESI-MS showed a major ion m/z 184.0 and a possible parent ion m/z 367.2 (MH⁺) suggesting that the product resulted from the reaction of 2,6-dimethoxy-p-quinone with hydroxylamine. However, mass spectral and other spectroscopic data indicated that the compound was neither of the 2,6-dimethoxy-p-quinone oximes. A product with identical absorbance, mass spectrum, electrophoretic mobility and HPLC retention time as the pigment from hydroxylamine extracts of flour was observed amongst the reaction products of hydroxylamine and 1,4-dihydroxy-2,6-dimethoxybenzene. The structure of this product was identified by NMR, 2D NMR and IR as 4,4′-dihydroxy-3,3′,5,5′-tetramethoxyazodioxybenzene. |
Keywords: | Wheat flour hydroxylamine hydroquinone oxime dimer |
DOI: | 10.1016/j.tet.2006.06.117 |
Description (link): | http://www.elsevier.com/wps/find/journaldescription.cws_home/942/description#description |
Published version: | http://dx.doi.org/10.1016/j.tet.2006.06.117 |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest 2 |
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