Photoinduced Generation of 2,3-Butanedione from Riboflavin

The volatile compound formation from riboflavin solution of a phosphate buffer (0.1 M, pH 6.5) under light for 15 h was studied by SPME-GC and SPME-GC/MS analysis. Only one major compound in the riboflavin solution was formed and increased as the light exposure time increased. The light-exposed ribo...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2007-01, Vol.55 (1), p.170-174
Main Authors: Jung, Mun Yhung, Oh, Young Seok, Kim, Dae Keun, Kim, Hyun Jung, Min, David B
Format: Article
Language:English
Subjects:
2,3-butanedione
Biological and medical sciences
Chromatography, Gas
Diacetyl - chemistry
Food industries
Fundamental and applied biological sciences. Psychology
ketones
odor compounds
Odorants - analysis
odors
Oxidation-Reduction
Photochemistry
photooxidation
riboflavin
Riboflavin - chemistry
Singlet Oxygen
Smell
Solutions
volatile organic compounds
Volatilization
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Summary:The volatile compound formation from riboflavin solution of a phosphate buffer (0.1 M, pH 6.5) under light for 15 h was studied by SPME-GC and SPME-GC/MS analysis. Only one major compound in the riboflavin solution was formed and increased as the light exposure time increased. The light-exposed riboflavin solution had a buttery odor. The compound of riboflavin solution under light was analyzed by gas chromatography and olfactometry. The major volatile compound eluted from the gas chromatograph had a buttery odor. The buttery odor compound was positively identified as 2,3-butanedione by a combination of gas chromatographic retention time, mass spectrum, and odor evaluation of authentic 2,3-butanedione. The addition of sodium azide, a singlet oxygen quencher, to riboflavin solution minimized the formation of the buttery odor compound. Singlet oxygen was involved in the formation of the buttery odor. The 2,3-butanedione was produced from the reaction between riboflavin and singlet oxygen. Singlet oxygen was formed from triplet oxygen by riboflavin photosensitization mechanism. This is the first reported oxidation reaction between riboflavin and singlet or triplet in food and biological systems. Keywords: Riboflavin; 2,3-butanedione; photosensitized oxidation; singlet oxygen
ISSN:0021-8561
1520-5118
DOI:10.1021/jf061999y