4,4′-Dihydroxy-3,3′,5,5′-tetramethoxyazodioxybenzene: an unexpected dimer formed during hydroxylamine extractions of wheat flour |
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Authors: | R.E. Asenstorfer D.J. Mares |
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Affiliation: | School of Agriculture and Wine, The University of Adelaide, Waite Campus, PMB 1, Glen Osmond, SA 5064, Australia |
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Abstract: | Neutral hydroxylamine extracts of wheat contained a product that was colourless at pH<5 (λmax 340 nm) and yellow at pH>9 (λmax 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. |
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Keywords: | Wheat flour Hydroxylamine Hydroquinone Oxime dimer |
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