Musk aldehyde

Other commonly occurring chemical groups ia essential oils iaclude aromatics such as P-phenethyl alcohol, eugenol, vanillin, ben2aldehyde, cinnamaldehyde, etc heterocycHcs such as iadole (qv), pyra2iaes, thia2oles, etc hydrocarbons (Liaear, branched, saturated, or unsaturated) oxygenated compounds such as alcohols, acids, aldehydes, ketones, ethers and macrocyclic compounds such as the macrocyclic musks, which can be both saturated and unsaturated. 

There are also, although not much met with, an aldehyde and a cyanide musk. The former is dinitro-tertiary - butyl-xylyl-aldehyde, Cg(CH3),C(CH3)3(NO,),CHO, melting at 112°, and the latter is diniti n-tertiary-butyl-xylyl-cyanide, Cg(CH3),CN. C(CH3)3(N03), melting at 110°. 

Similarity between odors arises because dissimilar substances or mixtures of compounds may interact with receptors to create similar sensory impressions in the sensory centers of the brain. The group of musk fragrances (comprising macro-cyclic ketones and esters as well as aromatic nitro compounds and polycyclic aromatics) are, for example, compounds with similar odors but totally different structures [5, 6]. Small changes in structure (e.g., the introduction of one or more double bonds in aliphatic alcohols or aldehydes) may, however, alter a sensory... 

What we notice immediately on examining the composition of the perfume is the almost complete absence of the classical fresh top note that we saw in the earlier perfumes, and the dominance of two materials, hedione (10%) and hexyl cinnamic aldehyde (12%), which with the musks make up some 30% of the formula. This is moving toward the type of structure that we associate with many of the modern linear perfumes. Anais Anais is a fragrance that remains comparatively unchanged throughout its evaporation. 

Anais Anais is another perfume that has been widely adapted for use in many types of functional product including soaps and fabric conditioners. Many of its components such as the salicylates, musks, woody notes, and aldehyde C14 are among the most substantive to cloth, while the floral notes are ideally suited to bring a natural and gentle quality to such products. 

Apart from the materials already mentioned the top note contains a simple mixture of bergamot and orange. The middle note is dominated by a traditional jasmin base, with muguet (hydroxycitronellal 10%), and rose. At the heart of the perfume is the classical chypre accord between vetiveryl acetate (10%), methyl ionone, oakmoss, aldehyde C14, coumarin, sandalwood, patchouli, musk ketone, and amber. The amber note can be reproduced by the simple but effective combination of labdanum, olibanum, and vanilla. Small amounts of other animalic notes such as civet may also be used. 

The perfume is perhaps as special for what it does not contain as for what it does. There are little or no aldehydes, synthetic musks, salicylates, patchouli, or vanillin. Although the floral and woody notes are reminiscent of some of the floral aldehydic perfumes, the green and mossy notes, together with the large amounts of orris and of Hedione, take it in an entirely different direction. 

In studies of the substantivity of nine aroma chemicals in a fabric softener application, head-space gas chromatography showed that benzyl salicylate, aldehyde C12 MNA, lilial, musk ketone, and the synthetic musk Fixolide were lost to a far lesser extent upon drying than were alpha ionone, eugenol, or linalool (Muller, Neuner-Jehle, and Etzweiler, 1992) (Figure 13.2). This result corresponds to the relative vapor pressures of these materials, except for aldehyde C12 MNA which is a special case. 

The most classical artificial substances used in perfumery are as follows (Figure 5). Hydroxycitronellal (99) was found to exhibit the odor of lily of the valley, the essential oil of which is not possible to prepare in the first place. Other classics include ct-amylcinnamaldehyde (100) and musk ketone (101), which were discovered to be good substitutes for jasmine and musk, respectively. Furthermore, perfume No. 5 (Chanel, launched 1921) contained 2-methylundecanal, 1 with so unique an aroma character that it established No. 5 as the pioneer of a new fragrance class — floral aldehydic. 

Neither dialdehydes nor dicarboxylic acids were detected and it was shown that this microbial oxidation had excellent regioselectivity. These generated co-hydroxy aldehydes could be used as starting materials for macrocyclic musk related compounds. The yields varied depending on the substrate concentration. Lower concentrations gave better yields. However, even at 3% concentration, the conversion ratio reached about 15% and co-hydroxy aldehydes were produced at about 5g/L medium. This figure was sufficient for production. 

The enzymic formation of aldehydes, ketones, alcohols, and oxoacids (from linoleic and linolenic acids) on disruption of plant tissues is an important biosynthetic pathway by which fruit and vegetable volatiles are formed. Some examples are (E)-2-hexenal ("leaf aldehyde") and ( )-3-hexenol ("leaf alcohol") in tea (E)-2-hexenal in apples (E,Z)-2,6-nonadienal ("violet Teaf aldehyde") and (E)-2-nonenal in cucumber ( Z)-5-nonenal in musk melon (Z,Z) -3,6-nonadienol in water melon, and 1-octen-3-ol ("mushroom alcohol") in certain edible mushrooms and Fungi. The enzyme system is highly substrate specific to a (Z,Z)-1,4-pentadiene system (like lipoxygenase) splitting the >C = C< double bond at the W - 6 and/or W - 9 position. Therefore linoleic-, linolenic-, and arachidonic acids are natural substrates. It seems to be a common principle in leaves, fruits, vegetables, and basidiomycetes. 

Ambergris is the most subtle of the animal perfumes. It is used to make floral scents appear richer and to round off perfumes with aldehydic character such as Chanel No.5. Civetone contributes a typical animal-like note, as in Jicky from Guerlain (Fig. 3.45). In Musk for Men OW Spice , dating fi om 1974, musk provides the only dominant basic scent. Combinations of musk, ambergris and oak moss are found in more than 50 % of all men s toiletries a typical representative is Tabac from the year 1959. Perfumes for ladies also make use of musk scents, as for example in Narciso Rodriguez . Synthetic muscone is used, since this possesses a smoother, less penetrant scent than animal musk. 

Different organic groups have been used in synthetic perfumes hydrocarbons, terpenes, sesquiterpenes, alcohols (dtronelol, geraniol, cinnamic alcohol), fenols (p-cresol, thymol), aldehydes (cuminaldehyde, vanillin), ketones (carvone, muscone, ionones, metilion-ones), lactones (nonalactone, undecalactone), esters (acetates, formates, butyrates), nitrogen compounds (indol, methyl anthranilate, musk xylol, quinoHnes). 

The 12 perfumes were split into five distinct clusters from the most woody, leather, oriental and patchouli such as Aromatic Elixir and Shalimar ET to the most floral, cilrusy, green and musk perfumes, such as Pleasure EP, J Adore EP and ET. The second axis (24% variance) compared the aldehydic perfumes, such as N 5 ET, to the most fruity perfumes, such as Angel EP. 

Muscone (40) is a sex pheromone of the musk deer and a chemical component of cosmetics. A 12-member library of racemic muscone analogs was synthesized by Nicolaou et al.," who anployed a cyclorelease method on solid support to form the macrocycle scaffold (Figure 11.17). A phosphonate-functionalized resin loaded on encoded SMART microreactors 36 was coupled to olelinic esters 35 to form the p-ketophosphonates 37. Sorting and cross olefin metathesis of 37 with two alkenols followed by oxidation with Dess-Martin reagent gave aldehydes 38. An intramolecular ketophosphonate-aldehyde condensation (Homer-Emmons-Wadsworth reaction) of 38 caused smooth cyclorelease of macrocyclic enones 39. Parallel solution-phase chemistry completed the sequence. 

Opdyke DLJ (1976) Inhibition of sensitization reactions induced by certain aldehydes. Fd Cosmet Toxicol 14 197-198 Panconesi E, Sertoli A, Spallanzani P, Giorgini S (1980) Balsam of Peru sensitivity from a perfumed cutting fluid in a laser factory. Contact Dermatitis 6 297-298 Parodi G, Guerrera M, Rebora A (1987) Lichenoid photocontact dermatitis to musk ambrette. Contact Dermatitis 16 136-138... 

IFRA and RIFM have forbidden the use of several essential oils and components, including costus root oil, dihydrocoumarin, musk ambrette, and balsam of Peru (Ford, 1991) a concentration limit is imposed on the use of isoeugenol, cold pressed lemon oil, bergamot oil, angelica root oil, cassia oU, cinnamic alcohol, hydroj citronellal, and oakmoss absolute. Cinnamic aldehyde, citral, and carvone oxide can only be used with a quenching agent. 

The most important natural sources of flavors are the essential oils derived from spices, fruits, and flowers as well as extractives and exudates (resins) from certain plant sources and animal secretions, e.g., musk. Essential oils are aromatic substances which are widely used in several industries such as perfume, pharmaceutical, food, and nutrition. These are mixtures of more than 200 compounds [14,16]. It contains monoterpenes, sesquiterpene hydrocarbons, and their oxygenated derivatives, along with aliphatic and aromatic aldehydes, alcohols, esters, and nonvolatile residues. Generally, terpenes are unsaturated com-... 

By the time Beaux composed No. 5, he used for the top note, ylang-ylang, neroli (spicy sweet floral) and aldehydes with 10-12 carbons, including branched 2-methylalkanals, especially 2-MNA for the middle, a mixture of jasmine, rose, lily of the valley and iris and for the base note sandalwood, vetiver, musk ketone (see p535), vanilla, civet and oak moss. 

Note of the long-chain fatty Aldehydic, e.g., fatty-sweaty, ironed laundry, seawater Typical notes from the animal kingdom, e.g., musk, castoreum, skatol, civet, amhergis... 

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