Novel 1,3-Dioxanes from Apple Juice and Cider
| Autor: | Dominique Kavvadias, Wilfried Schwab, Thorsten König, Barbara Boss, Martina Wein, Till Beuerle |
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| Rok vydání: | 1999 |
| Předmět: |
Magnetic Resonance Spectroscopy
Chromatography Food Handling Chemistry Silica gel Extraction (chemistry) Ms analysis Absolute configuration Enantioselective synthesis General Chemistry Chemical synthesis Gas Chromatography-Mass Spectrometry Beverages Dioxanes chemistry.chemical_compound Acetone Humans Fruit juice Rosales General Agricultural and Biological Sciences Chromatography Liquid |
| Zdroj: | Journal of Agricultural and Food Chemistry. 47:5178-5183 |
| ISSN: | 1520-5118 0021-8561 |
| DOI: | 10.1021/jf990714x |
| Popis: | Extracts obtained by XAD solid-phase extraction of apple juice and cider were separated by liquid chromatography on silica gel. Several new 1,3-dioxanes including the known 2-methyl-4-pentyl-1,3-dioxane and 2-methyl-4-[2'(Z)-pentenyl]-1,3-dioxane, were identified in the nonpolar fractions by GC/MS analysis and confirmed by chemical synthesis. The enantioselective synthesis of the stereoisomers of the 1,3-dioxanes was performed using (R)- and (R,S)-octane-1,3-diol and (R)- and (R,S)-5(Z)-octene-1,3-diol as starting material. Comparison with the isolated products indicated that the natural products consisted of a mixture of (2S,4R) and (2R,4R) stereoisomers in the ratio of approximately 10:1, except for 1,3-dioxanes generated from acetone and 2-butanone. It is assumed that the 1, 3-dioxanes are chemically formed in the apples and cider from the natural apple ingredients (R)-octane-1,3-diol, (R)-5(Z)-octene-1, 3-diol, (3R,7R)- and (3R,7S)-octane-1,3,7-triol, and the appropriate aldehydes and ketones, which are produced either by the apples or by yeast during fermentation of the apple juice. |
| Databáze: | OpenAIRE |
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