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Type: Journal article
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
Author: Wilkinson, K.
Elsey, G.
Prager, R.
Tanaka, T.
Sefton, M.
Citation: Tetrahedron, 2004; 60(29):6091-6100
Publisher: Pergamon-Elsevier Science Ltd
Issue Date: 2004
ISSN: 0040-4020
Statement of
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.
RMID: 0020081581
DOI: 10.1016/j.tet.2004.05.070
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Appears in Collections:Agriculture, Food and Wine publications

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