Elucidating the formation pathway of the off-flavor compound 6-propylbenzofuran-7-ol
| Autor: | Yoshiyuki Tateno, Susumu Ishizaki, Akira Nakanishi, Yasutaka Ohkubo, Akira Fujita, Kensuke Sakamaki |
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| Rok vydání: | 2012 |
| Předmět: |
chemistry.chemical_classification
Aldehydes Aqueous solution Hot Temperature General Chemistry Ascorbic Acid Ascorbic acid Hexanal Gas Chromatography-Mass Spectrometry Adduct Beverages Solutions chemistry.chemical_compound chemistry Fruit Malus Taste Michael reaction Organic chemistry Hemiacetal General Agricultural and Biological Sciences Citric acid Lactone Benzofurans |
| Zdroj: | Journal of agricultural and food chemistry. 60(40) |
| ISSN: | 1520-5118 |
| Popis: | In a previous work, we identified 6-propylbenzofuran-7-ol as an off-flavor compound formed from ascorbic acid and (E)-hex-2-enal in a test apple beverage. In this study, we elucidate the pathway by which 6-propylbenzofuran-7-ol formed. Isotope labeling studies revealed that the propyl group of 6-propylbenzofuran-7-ol derives from (E)-hex-2-enal and that 6-propylbenzofuran-7-ol contains carbons 2-6 of ascorbic acid. Two compounds, namely, 2,3-dihydro-6-propylbenzofuran-3,7-diol and 3-(2-furoyl)hexanal, were identified as byproducts of a model reaction of ascorbic acid and (E)-hex-2-enal. Each of these compounds was dissolved in an aqueous solution of citric acid and stored at 60 °C for 1 week. After storage, 6-propylbenzofuran-7-ol was detected from a solution of 2,3-dihydro-6-propylbenzofuran-3,7-diol, but not from 3-(2-furoyl)hexanal. 6-Propylbenzofuran-7-ol was formed by isolating tricyclic hemiacetal lactone derived from the Michael addition of ascorbic acid to (E)-hex-2-enal, mixing the tricyclic hemiacetal lactone with the aqueous solution of citric acid, and applying heat. This confirmed that 6-propylbenzofuran-7-ol was formed via the Michael adduct. |
| Databáze: | OpenAIRE |
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