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Riboflavin‐photosensitized singlet oxygen oxidation product of vitamin D 2
Author(s) -
King Joan M.,
Min David B.
Publication year - 2002
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-002-0591-6
Subject(s) - singlet oxygen , chemistry , riboflavin , vitamin , oxygen , photochemistry , singlet state , mass spectrometry , acetone , organic chemistry , chromatography , food science , biochemistry , physics , nuclear physics , excited state
The riboflavin‐photosensitized singlet oxygen oxidation of vitamin D 2 in a model system of 12% water and 88% acetone was studied to understand the possible oxidation of fortified vitamin D in milk. Only the samples containing vitamin D 2 and riboflavin under light storage showed two new peaks in the HPLC chromatogram, indicating that singlet oxygen oxidation of vitamin D 2 had occurred. UV analysis indicated that a new compound was formed from the reaction of the triene of vitamin D 2 with oxygen. The mass spectrum showed that one of the two compounds had a molecular ion at m/z =412, which was an increase of the mass of vitamin D 2 by the mass of exactly one oxygen. The IR spectrum suggested the presence of a hydroxyl group and no carbonyl group in the product. The combned information from UV, MS, and FTIR spectra and the chemical mechanisms of singlet oxygen oxidation of vitamin D 2 indicated that a 5,6‐epoxide of vitamin D 2 was formed from vitamin D 2 in the presence of riboflavin under light.