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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, 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
RMID: 0020061222
DOI: 10.1016/j.tet.2006.06.117
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Appears in Collections:Agriculture, Food and Wine publications

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