Asenstorfer, R.Mares, D.2007-02-202007-02-202006Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2006; 62(39):9289-92930040-4020http://hdl.handle.net/2440/23926Neutral 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.enWheat flourhydroxylaminehydroquinoneoxime dimerJournal article002006122210.1016/j.tet.2006.06.1170002404803000242-s2.0-3374717738752433Mares, D. [0000-0002-8165-8140]