1.Fragrance material review on cis-alpha-damascone.
Lapczynski A1, Lalko J, McGinty D, Bhatia S, Letizia CS, Api AM. Food Chem Toxicol. 2007;45 Suppl 1:S188-91. Epub 2007 Sep 14.
A toxicologic and dermatologic review of cis-alpha-damascone when used as a fragrance ingredient is presented.
2.Bioconversion of alpha-Damascone by Botrytis cinerea.
Schoch E1, Benda I, Schreier P. Appl Environ Microbiol. 1991 Jan;57(1):15-8.
Bioconversion of alpha-damascone (compound 1) was studied with four strains of Botrytis cinerea in grape must (pH 3.2). As biotransformation products of compound 1, 3-oxo-alpha-damascone, cis- and trans-3-hydroxy-alpha-damascone, gamma-damascenone, 3-oxo-8, 9-dihydro-alpha-damascone, and cis- and trans-3-hydroxy-8,9-dihydro-alpha-damascone were identified. In addition, acid-catalyzed chemical transformation of compound 1 to the diastereomers of 9-hydroxy-8,9-dihydro-alpha-damascone was observed. Identifications were performed by capillary gas chromatography (HRGC) and coupled HRGC techniques, i.e., on-line HRGC-mass spectrometry and HRGC-Fourier transform infrared spectroscopy, after extractive sample preparation.
3.Fragrance material review on alpha-damascone.
Lapczynski A1, Lalko J, McGinty D, Bhatia S, Letizia CS, Api AM. Food Chem Toxicol. 2007;45 Suppl 1:S179-87. Epub 2007 Sep 14.
A toxicologic and dermatologic review of alpha-damascone when used as a fragrance ingredient is presented.
4.Synthetic applications of enantioselective protonation and case study for (S)-alpha-damascone.
Fehr C1, Randall H. Chem Biodivers. 2008 Jun;5(6):942-57. doi: 10.1002/cbdv.200890106.
Among the fragrance compounds synthesized by enantioselective protonation, (S)-alpha-damascone, (R)-muscone, and (S,S)-Vulcanolide are the most prominent ones. (S)-alpha-damascone has been prepared by four different procedures: from the magnesium enolate, from the lithium enolate, from the enol, and from the corresponding thiol ester. We now present a new, industrially viable protocol for the addition of allyl magnesium chloride to the 'cyclogeranoketene' by a Barbier reaction, followed by protonation of the ensuing magnesium enolate by an aggregate formed from (-)-N-isopropylephedrine, lithium isopropylate, and acetic acid, furnishing (S)-alpha-damascone in 91% yield and with 71% ee.