Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/47351
Citations | ||
Scopus | Web of Science® | Altmetric |
---|---|---|
?
|
?
|
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: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2004; 60(29):6091-6100 |
Publisher: | Pergamon-Elsevier Science Ltd |
Issue Date: | 2004 |
ISSN: | 0040-4020 |
Statement of Responsibility: | 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. |
DOI: | 10.1016/j.tet.2004.05.070 |
Description (link): | http://www.elsevier.com/wps/find/journaldescription.cws_home/942/description#description |
Published version: | http://dx.doi.org/10.1016/j.tet.2004.05.070 |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest |
Files in This Item:
There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.