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|Title:||Precursors to oak lactone. Part 2: Synthesis separation and cleavage of several β-D-glucopyranosides of 3-methyl-4-hydroxyoctanoic acid|
|Other Titles:||Precursors to oak lactone. Part 2: Synthesis separation and cleavage of several beta-D-glucopyranosides of 3-methyl-4-hydroxyoctanoic acid|
|Citation:||Tetrahedron, 2004; 60(29):6091-6100|
|Publisher:||Pergamon-Elsevier Science Ltd|
|Kerry L. Wilkinson, Gordon M. Elsey, Rolf H. Prager, Takashi Tanaka and Mark A. Sefton|
|Abstract:||The β-D-glucopyranosides of all four stereoisomers of 3-methyl-4-hydroxyoctanoic acid have been prepared. The (3S,4S) and (3R,4R) species were prepared from cis-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone (cis-oak lactone) by a process involving ring-opening with base and protection of the carboxyl function as its benzyl ester. The glucose unit was introduced by a modified Koenigs–Knorr procedure. A different strategy was necessary for synthesis of the (3S,4R) and (3R,4S) compounds. This was based on the reductive ring-opening of trans-oak lactone and subsequent protection of the primary alcohol as its t-butyldiphenylsilyl ether. Separation of the individual glucosides was effected by preparative thin layer chromatography. Those corresponding to the nature-identical isomers of oak lactone have been shown to produce oak lactone under both acidic hydrolysis and pyrolysis conditions. The galloyl-β-D-glucoside of the cis-species, obtained as a natural isolate from the wood of Platycarya strobilacea, was also found to produce cis-oak lactone upon both acid hydrolysis and pyrolysis. Both the nature-identical (4S,5S) cis-oak lactone and its non-natural (4R,5R) enantiomer have been prepared from their corresponding glycosides and their aroma thresholds in white wine were determined to be 23 and 82 μg/L (ppb) respectively. The aroma threshold of the nature-identical isomer in a red wine was 46 μg/L.|
|Keywords:||Oak lactone; Glycosides; Hydrolysis; Pyrolysis; β-Glucosidase; Aroma thresholds|
|Description:||Copyright © 2004 Elsevier Ltd. All rights reserved.|
|Appears in Collections:||Agriculture, Food and Wine publications|
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