Topic
Calone
About: Calone is a research topic. Over the lifetime, 2 publications have been published within this topic receiving 16 citations.
Papers
TL;DR: In this article, the molecular influence on the dominant marine note attributed to the Calone 1951 (R) structure was determined by focusing on the polar structure fragment of the benzodioxepinone parent compound, and a selection of modifications of the ketone 1 resulted in a range of odor-active conformers with diverse olfactory attributes.
Abstract: Marine fragrances, particularly Calone 1951 (R) (= 7-methyl-2H- 1,5 -benzodioxepin-3 (4H) -one; 1) has carved a minor but distinct niche in the broad field of fragrance chemistry. By focusing on the polar structure fragment of the benzodioxepinone parent compound, we set out to determine the molecular influence on the dominant marine note attributed to the Calone 1951 (R) structure. A selection of one-step modifications of the ketone 1 resulted in a range of odor-active conformers with diverse olfactory attributes. The synthesis of a range of benzodioxepine analogues, i.e., of 3-11, is presented alongside olfactory evaluation (Tables 2 and 3). Removal of the carbonyl group of 1 and increasing the size of the aliphatic ring portion (see 6 and 7) introduced sweetness and a predominant loss of the marine character.
14 citations
TL;DR: It was found that a 7‐alkyl group in Calone 1951® was essential for the maintenance of the significant marine odor characteristic, and 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 is supported.
Abstract: The main marine message in perfumery is projected by Calone 1951(r) (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(r) 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(r) 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.
8 citations
Related Topics (5)
Performance Metrics
| Year | Papers |
|---|---|
| 2008 | 1 |
| 2007 | 1 |