4,4'-Dihydroxy-3,3',5,5'-tetramethoxyazodioxybenzene: an unexpected dimer formed during hydroxylamine extractions of wheat flour
Date
2006
Authors
Asenstorfer, R.
Mares, D.
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Journal article
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
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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.