Applications of biocatalysis in fragrance chemistry: the enantiomers of alpha-, beta-, and gamma-irones.

The history of iris extracts, and of the isolation and enzyme-mediated synthesis of their odoriferous principle, the "irones", will be used to describe the improvement brought about by chemistry and biocatalysis in the development of natural fragrances. In particular, this tutorial review will discuss how the progress in the field of enzyme chemistry allowed the optimisation of accelerated procedures for the preparation of natural irone extracts, and the synthesis of all the ten isomers of irone, starting from commercial irone alpha.

[1]  L. Saudan,et al.  Hydrogenation processes in the synthesis of perfumery ingredients. , 2007, Accounts of chemical research.

[2]  E. Corey,et al.  Enantioselective syntheses of georgyone, arborone, and structural relatives. Relevance to the molecular-level understanding of olfaction. , 2006, Journal of the American Chemical Society.

[3]  E. Brenna,et al.  Enantioselective perception of chiral odorants , 2003 .

[4]  E. Brenna,et al.  Enzyme-Mediated Syntheses of the Enantiomers of γ-Irones , 2001 .

[5]  E. Brenna,et al.  Enzyme-Mediated Preparation of (+)- and (−)-β-Irone and (+)- and (−)-cis-γ-Irone fromIrone alpha® , 2001 .

[6]  E. Brenna,et al.  Acetylation of Racemic cis‐ and trans‐α‐Irols, Mediated by Porcine Pancreatic Lipase (PPL) − A New Route to (−) and (+)‐cis‐α‐Irone , 2000 .

[7]  E. Brenna,et al.  Enzyme‐Mediated Preparation of (+)‐ and (–)‐cis‐α‐Irone and (+)‐ and (–)‐trans‐α‐Irone , 1999 .

[8]  E. Brenna,et al.  Enzyme-mediated synthesis of (R)- and (S)-α-ionone , 1998 .

[9]  A. Galfré,et al.  Direct enantioselective separation and olfactory evaluation of all irone isomers , 1993 .

[10]  W. König,et al.  Separation of enantiomeric irones by gas liquid chromatography on modified cyclodextrins , 1990 .

[11]  F. Marner,et al.  Studies on the Biosynthesis of Iridals and Cycloiridals , 1988 .

[12]  V. Rautenstrauch,et al.  On the Stereochemistry of Irones , 1984 .

[13]  F. Marner,et al.  Isolation and Structure Determination of the Precursors of a-and y-Irone and Homologous Compounds from Iris pallida and Iris florentina , 1983 .

[14]  C. Sih,et al.  Quantitative analyses of biochemical kinetic resolutions of enantiomers , 1982 .

[15]  L. Ruzicka,et al.  Veilchenriechstoffe. Die Konstitution des Irons , 1947 .

[16]  Y. Naves,et al.  Etudes sur les matières végétales volatiles L. Etudes dans les séries des méthyl‐3‐linalols, des méthyl‐3‐citrals et des méthyl‐6‐ionones , 1947 .

[17]  L. Ruzicka,et al.  Veilchenriechstoffe III. Über die Bruttoformel und einige Umsetzungen des Irons , 1933 .