4,4'-Dihydroxy-3,3',5,5'-tetramethoxyazodioxybenzene: an unexpected dimer formed during hydroxylamine extractions of wheat flour

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dc.contributor.authorAsenstorfer, R.
dc.contributor.authorMares, D.
dc.date.issued2006
dc.description.abstractNeutral 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.
dc.description.urihttp://www.elsevier.com/wps/find/journaldescription.cws_home/942/description#description
dc.identifier.citationTetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2006; 62(39):9289-9293
dc.identifier.doi10.1016/j.tet.2006.06.117
dc.identifier.issn0040-4020
dc.identifier.orcidMares, D. [0000-0002-8165-8140]
dc.identifier.urihttp://hdl.handle.net/2440/23926
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.source.urihttps://doi.org/10.1016/j.tet.2006.06.117
dc.subjectWheat flour
dc.subjecthydroxylamine
dc.subjecthydroquinone
dc.subjectoxime dimer
dc.title4,4'-Dihydroxy-3,3',5,5'-tetramethoxyazodioxybenzene: an unexpected dimer formed during hydroxylamine extractions of wheat flour
dc.typeJournal article
pubs.publication-statusPublished

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