Synthesis and Odor of Aliphatic Musks: Discovery of a New Class of Odorants

Kraft, Philip; Eichenberger, Walter

doi:10.1002/ejoc.200300578

Cited by 29 publications

(33 citation statements)

References 12 publications

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“…We found that the introduction of the CC bond indeed had a major impact on the intensity and character of the compounds. 10 times weaker than 23 [27]. 5 ± 6 times more powerful than Helvetolide (23).…”

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confidence: 94%

“…Starting from artemone ( 1-(3,3-dimethylcyclohex-1-enyl)ethanone) and 1-(5,5dimethylcyclohex-1-enyl)ethanone, available by Rupe rearrangement of ethynylcyclohexanol, we prepared the unsaturated analogs 27, 28, 29, and 30 of Helvetolide (23) and Romandolide (24) [27]. We found that the introduction of the CC bond indeed had a major impact on the intensity and character of the compounds.…”

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confidence: 99%

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‘Brain Aided’ Musk Design

Kraft

2004

Chemistry & Biodiversity

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This brief review, including new experimental results, is the summary of a talk at the RSC/SCI conference flavours & fragrances 2004 in Manchester, United Kingdom, 12-14 May, 2004. Musk odorants have been a classical domain for computer aided structure-odor relationship (SOR) studies, but, contrary to sandalwood or amber odorants, they belong to structurally very different substance classes, e.g., macrocycles, aromatic polycycles, and nitro arenes. Most SOR computer models are restricted to one class, excluding structural diversity to increase predictability. But even within a musk family, structural similarities are often due to a common synthetic access, and do not reflect binding requirements for the musk receptor. Beyond that, the importance of structural key features can be missed, which is discussed on the example of the (4S)-Me group of Galaxolide. By synthesis and olfactory evaluation of Galaxolide-like shaped macrobicycles as model compounds for conformationally constrained (12R)-12-methyltridecano-13-lactone, it was investigated how likely there is more than one musk receptor. Finally, the new family of so-called linear musks is discussed, especially with respect to the conformational importance of the gem-2',2'-dimethyl moiety in Helvetolide and the additional 2'-carbonyl group of Romandolide--structural features that strongly diminish the musk odor of macrocycles. On the example of 2-methyl-2-[(E)-1,2,4-trimethylpent-2-enyloxy]propyl esters, the 'brain-aided' design and conformational analysis of musk odorants is illustrated. The overview concludes with the synthesis, odor evaluation, and conformational discussion of the new musk odorant 2-(3,3-dimethylcyclohexyl)propanoic acid ethoxycarbonylmethyl ester.

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‘Brain Aided’ Musk Design

Kraft

2004

Chemistry & Biodiversity

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“…Unfortunately, when reduced with 0.5 mol-equiv. of LiAlD 4 , ester (À)-16d was prone to a more rapid 1,4-hydride addition, leading to the dideuterated aldehyde (À)-20 16 ) 17 ) in 70% yield [11a] [14] 6 ). This drawback was overcome by oxidizing the monodeuterated allyl alcohol (À)-17a (pyridinium chlorochromate (PCC), CH 2 Cl 2 , yield > 90%) to a ca.…”

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“…As examples of a musk-like perfume ingredient (Scheme 6), we esterified the known intermediate alcohols (þ)-21a [15] and (þ)-21b [16] [17] 6 ) (yield 93%), respectively. In the first case, measurement is made with the major peak at m/z 132/129, and confirmed with the m/z 60/57 fragment.…”

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Synthesis of Deuterium‐Labeled Perfume Ingredients as Internal Standards for Their GC/MS Quantification

Chapuis

Cantatore

Fankhauser

et al. 2009

Helvetica Chimica Acta

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The synthesis of various D-labeled perfume ingredients (orris-like, sandalwood-like, musky, and amber-like) is presented. These substances, possessing practically identical H 2 O/solid and solid/gas partition coefficients as their unlabeled analogues, are used as internal standards for the validation of a new analytical GC/MS method for the determination of low residual concentrations in H 2 O after biodegradability tests.

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“…The ethyl malonate 8 was described as the molecule with the strongest musk odor. Last but not least, Kraft and Eichenberger of Givaudan [9] introduced a CC bond in the cyclohexyl moiety of 9, with the side chains unaltered. All synthesized molecules of this type possess musk odors with different connotations.…”

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New Alicyclic Musks: The Fourth Generation of Musk Odorants

2004

Chemistry & Biodiversity

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Musk odorants are one of the most important classes of fragrances in perfumery because they impart sensuality to perfume-oil compositions. Among the three well-known classes of musks, a new and very exciting generation of musk odorants, the so-called alicyclic musks, was discovered recently, of which Helvetolide (2) and Romandolide (3) are the most popular representatives so far. To find new, structurally related alicyclic musks, we have synthesized a library of 114 unique alicyclic molecules with modified cyclohexyl moieties. The olfactory properties of all compounds were evaluated to identify the structural requirements to be met for a musk odorant.

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Synthesis and Odor of Aliphatic Musks: Discovery of a New Class of Odorants

Cited by 29 publications

References 12 publications

‘Brain Aided’ Musk Design

‘Brain Aided’ Musk Design

Synthesis of Deuterium‐Labeled Perfume Ingredients as Internal Standards for Their GC/MS Quantification

New Alicyclic Musks: The Fourth Generation of Musk Odorants

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