Article

The sherry-lactones and solerone. Their identification in dried figs

  1. R. Näf*,
  2. A. Jaquier,
  3. A. F. Boschung,
  4. M. Lindström

Article first published online: 28 APR 2006

DOI: 10.1002/ffj.2730100404

Issue

Flavour and Fragrance Journal

Flavour and Fragrance Journal

Volume 10, Issue 4, pages 243–247, July/August 1995

Additional Information

How to Cite

Näf, R., Jaquier, A., Boschung, A. F. and Lindström, M. (1995), The sherry-lactones and solerone. Their identification in dried figs. Flavour and Fragrance Journal, 10: 243–247. doi: 10.1002/ffj.2730100404

Author Information

  1. Firmenich SA, Research Laboratories, PO Box 239, CH-1211 Geneva 8, Switzerland

*Firmenich SA, Research Laboratories, PO Box 239, CH-1211 Geneva 8, Switzerland

Publication History

  1. Issue published online: 28 APR 2006
  2. Article first published online: 28 APR 2006
  3. Manuscript Accepted: 31 OCT 1994
  4. Manuscript Received: 17 SEP 1994

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Keywords:

  • dried figs;
  • Ficus carica L;
  • sherry-lactones;
  • solerone;
  • enantiomers;
  • sharpless synthesis

Abstract

The two diastereoisomers of sherry-lactone (5-hydroxy-4-hexanolide, 1 and 2) and the corresponding ketone (5-keto-4-hexanolide = solerone, 3) were identified in a solvent extract of dried figs and their enantiomeric distributions were determined. The (4S,5S)- and the (4R,5R)-enantiomers of diastereoisomer 1 were selectively synthesized following the method of Sharpless (asymmetric dihydroxylation) and their optical rotations were measured. Diastereoisomer 2 was isolated as an almost racemized by-product. Racemic ketone 3 was obtained by oxidation of either (4S,5S)- or (4R,5R)-1.

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