Cyclamen aldehyde

The process mentioned above was successfully applied to a short and efficient synthesis of two perfume compounds, cyclamen aldehyde and foliaver (Scheme 10).32... 

Cyanuric chloride method, for covalent ligand immobilization, 6 396t Cycads, in nitrogen fixation, 2 7 300 Cyclamate, 22 42 24 234, 236 sweeteners, 2 513-514 Cyclamen aldehyde, aroma chemical derived from toluene, 3 234 Cyclams, 24 41—42... 

Cyclamen aldehyde Muguet aldehyde Dupical Aldehyde C7 Aldehyde CIO Oncidal... 

Floral modifiers Linalool Cyclamen aldehyde Lilial... 

The green side of the perfume which is less pronounced than in Fidji, and more floral, is based on phenylacetaldehyde and cA-3-hexenyl acetate with perhaps a trace of galbanum. Narcisse absolute may also be used. Other materials that add to the building up of the white flower character are Lilial and cyclamen aldehyde in addition to the hydroxycitronellal and Lyral. The tuberose character can be given by the use of the Schiff base derived from methyl anthranilate and Helional, or by the direct addition of methyl anthranilate. The mossy side of the perfume is represented by Evemyl. 

In the first type, which includes aldehyde C12 lauric and phenylacetaldehyde, the balance of the reaction lies in favor of the combined molecule. In the second, however, to which belong aldehyde C12 MNA, cyclamen aldehyde, hydratropic aldehyde, and Lilial, the balance lies more toward the original material. Most ketones also behave in this way. The third type, which includes amyl and hexyl cinnamic aldehydes, do not undergo the aldol reaction and are therefore more stable. Aldehydes such as anisaldehyde and Triplal, in which the —CHO is linked directly to a ring structure, are also less reactive. 

The nomenclature of the aromatic aldehydes is somewhat confusing because in the past a number of different conventions were used in the naming of organic compounds. While some, such as cyclamen aldehyde, and vanillin, are usually referred to by their common names, others are referred to either by a single chemical name or by a number of different chemical synonyms. 

C15H22 5-hexyl-2,3-dihydro-1 H-indene 54889-55-3 565.25 50.187 1,2 28773 C15H2402 cyclamen aldehyde dimethyl acetal 29886-96-2 523.15 46.113 2... 

Each odour is smelled by the panellist, who then scores the perceived intensity of each odour character that she or he can detect (referring to the set of standard odour references for clarification if necessary), which results in a sensory profile for that odour. A minimum of at least 20 profiles is usually collected for each sample and an average profile is then calculated. A set of typical odour profiles is shown in Figure 8.3. These profiles show the differences in perceived intensity of 13 odour characteristics identified in seven perfume materials, and immediately it is possible to see that although all of the materials are floral or muguet in character, one material is far more fruity (cyclamen aldehyde) and another (Mayol ) is far more herbal than the other materials. 

The samples are grouped so that those that are most similar in odour character are closest together on the map (e.g. Lilial and Bourgeo-nal ), and those that are most different are furthest apart (e.g. cyclamen aldehyde and Lyral ). The arrows indicate the direction of increasing perception of the odour characteristics shown. Only the odour characteristics that significantly correlate with the distribution of the samples across the map are shown these are the characteristics that are responsible for the systematic differences between the samples. 

All the materials were perceived to be floral and muguet in character, so these characteristics are not shown on the map. Cyclamen aldehyde, Lilial and Bourgeonal are the most fruity of the samples and are grouped together on the right-hand side of the map, while Lyral and... 

In the sections above, the sensory profiling and multidimensional scaling techniques are illustrated using data obtained from the analysis of muguet perfumery materials. From a purely olfactory point of view, the type of odour that best fits the odour described in this brief is cyclamen aldehyde, but with the range of products that need to be considered in this brief the choice of material is not quite so simple. 

Since the blossom oil of lily of the valley is not commercially available, the perfumers have to rely on synthetic substitutes, such as hydroxy-citronellal (1), Lilial (3) and Bourgeonal (6) to create their muguet fragrances. The oldest lily of the valley odorants, hydroxycitronellal and cyclamen aldehyde (2) (Winthrop Chem. Corp., 1929), were discovered by chance. Serendipity still continues to play an important role. Anselmi et al. (1992) synthesized and organoleptically screened a series of 38 tetrahydropyranyl ethers. This class of compounds was chosen because of their ease of synthesis and purification, and because of their stability in alkaline media, conditions under which aldehydes tend to undergo aldol condensations. Two compounds (24 and 25) were described as having a white, floral odour reminiscent of hydroxycitro-... 

Another example of analogue synthesis dates back to the 1960s. As mentioned above, the first phenylpropanal to be discovered with a white, floral odour was cyclamen aldehyde, 3-(4-isopropylphenyl)-2-methylpropanal (2). As the name implies, its odour is reminiscent of wild cyclamen. However, at low concentrations the odour possesses a hydroxycitronellal-like note. Consequently, it was common practice in the 1960s to replace hydroxycitronellal, which is unstable in alkaline media and irritating to the skin, with cyclamen aldehyde. However, from an odour point of view the substitution was not entirely satisfactory. The discovery of the closely related r-butyl analogues (3 and 6) resulted in a certain improvement (Givaudan Corp., 1959 Boelens and Wobben, 1980). Both of these compounds have a more pronounced muguet floral odour. 

Berends and van der Linde (1967) synthesized and organoleptically-assessed 24 analogues of cyclamen aldehyde (26). They varied the nature of the alkyl substituent in the para position, altered the position... 

---