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Chem Biodivers

Title:		Marine fragrance chemistry
Author(s):		Hugel HM; Drevermann B; Lingham AR; Marriott PJ;
Address:		"School of Applied Sciences (Chemistry), RMIT University, GPO Box 2476V, Melbourne, Victoria 3001, Australia. helmut.hugel@rmit.edu.au"
Journal Title:		Chem Biodivers
Year:		2008
Volume:		5
Issue:		6
Page Number:		1034 - 1044
DOI:		10.1002/cbdv.200890083
ISSN/ISBN:		1612-1880 (Electronic) 1612-1872 (Linking)
Abstract:		"The main marine message in perfumery is projected by Calone 1951 (7-methyl-2H-1,5-benzodioxepin-3(4H)-one). Kraft (Givaudan) and Gaudin (Firmenich) further maximized the marine fragrance molecular membership by extending the carbon chain of the 7-Me group. Our research targeted the polar group of the benzodioxepinone parent compound to investigate how this region of molecular makeup resonates with the dominant marine fragrance of the Calone 1951 structure. The olfactory evaluation of analogues prepared by chemical modification or removal of the CO group resulted in the introduction of aldehydic, sweet and floral-fruity notes with a diluted/diminished potency of the marine odor. To further analyze the olfactory properties of benzodioxepinones containing a diverse range of aromatic ring substituents, a novel synthesis route was developed. We found that a 7-alkyl group in Calone 1951 was essential for the maintenance of the significant marine odor characteristic, and our studies support the concept that the odorant structure occupying the hydrophobic binding pocket adjacent to the aromatic ring-binding site of the olfactory receptor is pivotal in the design and discovery of more potent and characteristic marine fragrances. How the structure of benzodioxepinones connects to marine sea-breeze fragrances is our continuing challenging research focus at the chemistry-biology interface"
Keywords:		Benzoxepins/*chemistry Molecular Structure Odorants/*analysis *Perfume/chemical synthesis/chemistry Structure-Activity Relationship;
Notes:		"MedlineHugel, Helmut M Drevermann, Britta Lingham, Anthony R Marriott, Philip J eng Switzerland 2008/07/12 Chem Biodivers. 2008 Jun; 5(6):1034-44. doi: 10.1002/cbdv.200890083"