Castoreum

Biber, m. beaver, -geil, n, castor, castoreum. -geilkampher, m, castorin. -nell, -nelle, /. burnet saxifrage (Pimptnella saxifraga). -schwanz, m. flat roofing tile. 

Until recently, most of the chemical research on the contents of these structures was directed at the identification of the constituents of castoreum. In the late 1940s Lederer [72, 73] identified 36 compounds and some other incompletely characterized constituents in castoreum of uncertain origin. Other constituents were subsequently identified in the material [74-77]. In a reinvestigation aimed specifically at the phenol content of the material, Tang et al [69] identified 10 previously unreported phenols in the castoreum from the North American beaver, Castor canadensis. Of the 15 phenols reported elsewhere, only five were confirmed in this analysis, in addition to 10 phenolic compounds that were not reported elsewhere. It was concluded that the 10 previously identified phenols that were not found in the study by Tang et al. were either absent or were not volatile enough to be detected by the methods employed. This was most probably because a relatively low maximum column temperature of only 210 °C was employed in the GC-MS analyses. The compounds identified by Lederer,... 

Recently, Rosell and Sundsdal [78] tentatively identified 21 of the 43 constituents present in 96 scent marks deposited directly on snow or ice mounds by the Eurasian beaver, C. fiber. In this study, a higher final oven temperature was employed and several steroids were eluted from the capillary column. Because the main focus of this study was to determine whether the beaver uses castoreum and/or anal gland secretion for scent marking and not the full chem-... 

The differences between castoreum from different species and sources still need to be investigated. As suggested by Tang et al [69] it is quite likely that these differences could be diet related because the phenols are most likely derived from the diet of these animals. Indeed, already in 1949 Lederer [73] recognized this possibility and pointed out that 2, 3"-dihydroxydibenz-2-pyrone and 4,4 -dihydroxydiphenic acid dilactone 12 (Fig. 3) are closely related to ellagic acid, which is abundant in the bark of trees. A comprehensive chemical analysis of the polyphenols present in the preferred diet of the beavers and a comparison of these compounds with the phenols present in castoreum from animals fed exclusively on this diet could shed some light on this unresolved problem. 

The interdigital secretion of the red hartebeest, A. b. caama, consists of fewer compound classes. It contains a few alkanes and short-chain, branched alcohols, fatty acids, including a few of the higher fatty acids up to octadecanoic acid, an epoxide and the cyclic ethers, rans-(2 ,5.R)-furanoid linalool oxide 23, as-(2JR,5S)-furanoid linalool oxide 24 and ds-(2S,5i )-furanoid linalool oxide 25 (Fig. 5) in a ratio of 2.5 1 1.5 respectively [138]. From the point of view that many of the constituents of the interdigital secretion of this animal are probably of microbial origin, it is interesting that cis- and trans- furanoid linalool oxides have also been found in castoreum [77]. 

It is less likely that beavers will colonize unoccupied beaver sites if these sites are artificially scented with castoreum and anal scent secretion (Welsh and Muller-Schwarze, 1989). 

Beaver Castor fiber Eeces, urine, castoreum, AGS Rosell andNolet, 1997... 

If artificial castoreum scent marks are placed on the banks of a pond, beavers, C. canadensis, are more likely to visit, destroy, and re-mark the sites as the complexity of the artificial odor composition increases (Fig. 6.14). While some single phenolics from castoreum such as 4-ethylphenol trigger marking (Miiller-Schwarze and Houlihan, 1991), the response increases as the mixture grows to 4, 6,10,13, and finally 15 compounds. A mixture of 14 phenolics and 12 neutrals (mostly oxygenated monoterpenes) released responses almost as strong as whole castoreum (Schulte etal., 1995). 

Castoreum of beaver (Castor canadensis) function, chemistry and biological activity of its components. In Chemical Signals in Vertebrates, vol. 6, ed. R. L. Doty, and D. Muller-Schwarze, pp. 457-464. New York Plenum. 

Muller-Schwarze, D. and Houlihan, D. (1991). Pheromonal activity of single castoreum constituents in beaver. Castor canadensis. Journal of Chemical Ecology 17, 715-734. 

The classical scent of the sea is afforded by ambergris, which is also the best fixative for perfumes. Once secured from whales, ambergris can now be legally provided by chemical synthesis (Science whaling 2000). Other fixatives are obtained from land animals, such as castoreum, civet, and musk. The first one is a phenolic substance and the latter two macrocyclic ketones that have stimulated the earfy methodologies for the synthesis of macrocyclic conqjoimds... 

Castoreum p-methoxyphaiol, p-ethylphaiol, acetophencme, and l -benzenediol/armnatics and d radation products oily cream found in the sac of beavers Castor spp., Mamm. /fixative in all perfiunes, particularly leather, amber, and re perfumes Magie Noire (LancSme), Em ude (Coty), and Arpfege (Lanvin)... 

Castoreum is an unpleasantly sharp-smelling, oily substance secreted by special glands of beavers. Castor fiber L. (Castoridae), living in Canada, Alaska, and Siberia. Both sexes secrete the substance, which accumulates in an abdominal pouch, also called castoreum. Dilute castoreum (e.g., as a tincture in ethanol) smells pleasantly of birch tar and musk and is slightly fruity. 

Castoreum is a byproduct of the fur industry. The beaver pouches are dried in the air or over a wood fire, the color of their contents then changes from yellow to dark brown, and the consistency from a butter-like to resinous character. 

In addition to alcoholic tinctures, castoreum is available in the form of resinoids, which are prepared by extracting dried, comminuted pouches with suitable solvents. 

The intense, for the Siberian beaver leathery, odor of castoreum is caused largely by phenolic compounds (e.g., 4-alkylphenols and catechol derivatives [256]), which beavers take in with their food and excrete into their abdominal pouch. Castoreum was used mainly in fine fragrances for its characteristic, long-lasting odor, particularly for delicate leather nuances. FCT 1973 (11) p. 1061 [8023-83-4], [92704-04-6], [92704-05-7]. 

Benzyl alcohol (1) occurs widely in essential oils both as the free alcohol, and, more importandy from a fragrance standpoint, in the form of various esters. Although benzyl alcohol itself is rather bland in odor, combined with its much more fragrant esters it is an important part of the odor of jasmine, ylang-ylang, gardenia, some rose varieties, narcissus and peony, as well as castoreum, balsams of peru and tolu, and propolis. Benzyl alcohol occurs primarily in flower oils and tree exudates, whereas a large number of essential oils obtained from other parts of a wide variety of plants contain no benzyl alcohol or its esters (1). 

All contain sweet balsamic notes—such as benzoin, tolu and opoponax—amber notes based on labdanum, and castoreum, with rose as the dominant floral. 

Castoreum is of particular importance in Shalimar, forming the basis of the leather aspect of the perfume, which may be further developed by the use of a leather base, such as a classic Cuir de Russie. The same idea was used by Guerlain in Mitsouko, one of the earliest of the chypre perfumes to contain also a fruity note based on aldehyde C14 (undecalactone). Cinnamon bark oil, which forms part of the spicy aspect of the perfume, fits in perfectly with the leather. Other spices that work well are coriander, nutmeg, and clove. 

At the time when Shalimar was made it was customary to use a high proportion of the alcoholic tinctures made from natural products, rather than the concentrated absolutes and resins. These would have included such products as vanilla, benzoin, and tonka to give naturalness to the ethyl vanillin and coumarin, as well as tinctures of civet, castoreum, ambergris, and musk. Such products retain more of the most volatile components of the starting material, giving a wonderful quality and life to the finished product. 

Otherwise, in general construction the perfume follows closely that of a classical oriental, with citrus oils (making up some 25%), lavender, sandalwood, patchouli, vanillin, coumarin, castoreum, and rose. The general sweetness of the perfume is further enhanced by the choice of musk materials, Galaxolide (5%), Tonalid, ethylene brassylate, and musk ketone, as well as by the use of Cashmeran, an intensely sweet fruity musk material associated with the synthesis of Galaxolide. 

In Opium the two types of oriental, represented by Youth Dew and Shalimar, are brought together by the combination of the mellis and ambreine accords. Again there is an emphasis on castoreum, and on the spicy and balsamic notes, with the rose aspect being more fully developed than in either of its forebears. 

The ability of Hedione to combine successfully with many of the most important perfumery materials has been one of the major influences in perfumery over the past 30 years. Nowhere is this better seen than in a group of perfumes based on its relationship with patchouli. Although sometimes classified as chypres, the dominance of floral notes and patchouli, and the comparative lack of musk and animalic notes, other than castoreum, justifies the placing of them in a separate group. 

Other aspects of the perfume are its balsamic notes such as benzoin which, with castoreum and a costus note (the natural product can no longer be used), combine with the isobutyl quinoline to give the leather character. As we have seen before, spices such as cinnamon and clove work well with leather notes, and these are again present, backed up by a carnation accord of eugenol, heliotropin, and vanillin. 

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