New Alicyclic Musks: The Fourth Generation of Musk Odorants

Abstract

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.

Preparation of Musk‐Smelling Macrocyclic Lactones from Biomass: Looking for the Optimal Substrate Combination

“…[22][23][24][25] The latter reaction is more useful as it resultsi na more valuable product containing at erminal C-C double bond and fewer byproducts, although form any years there had been al ack of effective catalysts resistantt oe thylene, moisture, and polar contaminants present in the substrates. Originally musks were divided into four groups: nitro musks such as moskene obtained by Albert Baur in 1888, macrocyclic musks such as muscone [33] and egzaltolide, [34] with one ring functionalized mainly with keto or ester groups as the core of the compound, polycyclic musks such as galaxolide, [35] made up of several smaller rings connected to each other,and, finally,a cyclic otherwise knowna sc ycloalkyl ester or linear musks [36] fore xample, helvetolide .F rom these four different groupso fc ompounds, only the macrocyclic musks-identical to those derived from naturallyo ccurring musks, such as civetone or ambergris-have been used in fragrance formulations for the longest time. [1,26] As olefin metathesis can be used for the construction of macrocyclic rings [27][28][29][30][31][32] it is logical to apply it also in the F + F (flavours and fragrances) industry in the synthesis of the macrocyclic musks.…”

“…[1,26] As olefin metathesis can be used for the construction of macrocyclic rings [27][28][29][30][31][32] it is logical to apply it also in the F + F (flavours and fragrances) industry in the synthesis of the macrocyclic musks. Originally musks were divided into four groups: nitro musks such as moskene obtained by Albert Baur in 1888, macrocyclic musks such as muscone [33] and egzaltolide, [34] with one ring functionalized mainly with keto or ester groups as the core of the compound, polycyclic musks such as galaxolide, [35] made up of several smaller rings connected to each other,and, finally,a cyclic otherwise knowna sc ycloalkyl ester or linear musks [36] fore xample, helvetolide .F rom these four different groupso fc ompounds, only the macrocyclic musks-identical to those derived from naturallyo ccurring musks, such as civetone or ambergris-have been used in fragrance formulations for the longest time. Because of the risk of bioaccumulation and toxicityo fn itro and polycyclic musks they are no longer in use.…”

New Norbornyl Derivatives as Woody Fragrant Materials

“…In the context of new linear musks with an alicyclic moiety [11], and since Legnox and 13 were found to have an interesting woody fragrance, esters with a structural similarity to Helvetolide and Romandolide (Fig. 2) were also envisaged.…”

“…2) are well known for their woody, ambery, or musky odors [11], it seemed also appealing to prepare similar derivatives from Presantone (1) or its derivative Presantone H (2), and evaluate the influence of the norbornyl group on the odor perception.…”

Quantum Calculation for Musk Molecules Infrared Spectra towards the Understanding of Odor

“…Musks are responsible for bringing sensuality and warmth to a fragrance [1], as well as adding their excellent fixative properties [2,3]. Presently, natural products extraction involves high costs and generates small amounts of raw material, so synthetic odorants are greatly demanded.…”