The Chemistry and Fragrance of Natural Musk Compounds

Mookherjee, Braja D.; Wilson, Richard A.

doi:10.1016/b978-0-12-685850-1.50017-6

Cited by 16 publications

(4 citation statements)

References 115 publications

(62 reference statements)

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“…The identification of three vibrational bands as defining musk odor can be applied to the baffling structure-odor relation between ring length and musk character in musk ketones, first described by Dyson in 1929 (see Mookherjee & Wilson, 1982). When cyclic ketones of increasing ring length are synthesized, it is found that only rings with 14 and 15 carbons (C14 and C15) have a musk odor.…”

Section: Macrocyclic Ring Length and The Musk Odor Charactermentioning

confidence: 98%

A Method for the Calculation of Odor Character from Molecular Structure

Turin

2002

Journal of Theoretical Biology

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Section: Macrocyclic Ring Length and The Musk Odor Charactermentioning

confidence: 98%

A Method for the Calculation of Odor Character from Molecular Structure

Turin

2002

Journal of Theoretical Biology

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“…Pathways enriched in all groups illustrated that these bacteria are involved in the metabolism antibiotics and terpenoids, which are essential for the synthesis of antibacterial and anti-inflammatory components and specific odor substances in musk. For example, ansamycin and vancomycin are antibiotics used for the treatment of bacterial infections ( Yu et al, 2002 ; Watanabe et al, 2003 ; Okano et al, 2017 ); terpenoids are the precursor of sterols and ketones ( Mookherjee and Wilson, 1982 ; Wriessnegger and Pichler, 2013 ), and they are microbial metabolites of Streptomycetaceae ( Hwang et al, 2014 ), Actinobacteria ( Actinomycetes and Corynebacterium ) ( van Bergeijk et al, 2020 ), Myxobacteria ( Schaberle et al, 2014 ) and Proteobacteria ( Escherichia coli ) in industry ( Yamada et al, 2015 ; Lee et al, 2016 ; Wang et al, 2018 ). Among PMSP-specific pathways, the PTS is a major mechanism used by bacteria for the uptake of carbohydrates ( Deutscher et al, 2008 ), which is related to the accumulation of carbohydrates and other amino acids at PMSP.…”

Section: Discussionmentioning

confidence: 99%

Chemical composition and microbiota changes across musk secretion stages of forest musk deer

Xu,

Li,

Liu

et al. 2024

Front. Microbiol.

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Forest musk deer is the most important animal for natural musk production, and the musk composition changes periodically during musk secretion, accompanied by variation in the com-position of deer-symbiotic bacteria. GC-MS and 16S rRNA sequencing were conducted in this study, the dynamic changes to correlated chemical composition and the microbiota across musk secretion periods (prime musk secretion period, vigorous musk secretion period and late musk secretion period) were investigated by integrating its serum testosterone level in different mating states. Results showed that the testosterone level, musk composition and microbiota changed with annual cycle of musk secretion and affected by its mating state. Muscone and the testosterone level peaked at vigorous musk secretion period, and the microbiota of this stage was distinct from the other 2 periods. Actinobacteria, Firmicutes and Proteobacteria were dominant bacteria across musk secretion period. PICRUSt analysis demonstrated that bacteria were ubiquitous in musk pod and involved in the metabolism of antibiotics and terpenoids in musk. “Carbohydrates and amino acids,” “fatty acids and CoA” and “secretion of metabolites” were enriched at 3 periods, respectively. Pseudomonas, Corynebacterium, Clostridium, Sulfuricurvum were potential biomarkers across musk secretion. This study provides a more comprehensive understanding of genetic mechanism during musk secretion, emphasizing the importance of Actinobacteria and Corynebacterium in the synthesis of muscone and etiocholanone during musk secretion, which required further validation.

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“…Yet both smell musky and utterly lack the burnt character associated with deuterated musks. [22,23]. Therefore it is hard to see how such differences could be responsible for the change in odor character of the deuterated cyclopentadecanone, which is perceptible over a large range of concentrations, from pure to dilute GC puff.…”

Section: Discussionmentioning

confidence: 99%

Molecular vibration-sensing component in human olfaction

2013

Br Dent J

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Whether olfaction recognizes odorants by their shape, their molecular vibrations, or both remains an open and controversial question. A convenient way to address it is to test for odor character differences between deuterated and undeuterated odorant isotopomers, since these have identical ground-state conformations but different vibrational modes. In a previous paper Proc Natl Acad Sci USA 108:9, 3797-802) we showed that fruit flies can recognize the presence of deuterium in odorants by a vibrational mechanism. Here we address the question of whether humans too can distinguish deuterated and undeuterated odorants. A previous report (Keller and Vosshall (2004) Nat Neurosci 7:4, 337-8) indicated that naive subjects are incapable of distinguishing acetophenone and d-8 acetophenone. Here we confirm and extend those results to trained subjects and gas-chromatography [GC]-pure odorants. However, we also show that subjects easily distinguish deuterated and undeuterated musk odorants purified to GC-pure standard. These results are consistent with a vibrational component in human olfaction.

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The Chemistry and Fragrance of Natural Musk Compounds

Cited by 16 publications

References 115 publications

A Method for the Calculation of Odor Character from Molecular Structure

A Method for the Calculation of Odor Character from Molecular Structure

Chemical composition and microbiota changes across musk secretion stages of forest musk deer

Molecular vibration-sensing component in human olfaction

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