Aldehydes synthetic fatty

Aldehydes h ive very powerful aromas and widespread use in the perfumery industry. Chanjel No. 5 is described as having an aldehydic smell. The aldehydes used in perfumery are not the terpene derivatives but are usually synthetic fatty aldehydes. 

Unsaturated and saturated fatty aldehydes such as (Z, Z, Z)-8, 11, 14-heptadecatrienal, (Z, Z)-8, 11-heptadecadienal, (Z)-8-heptadecenal, (Z, Z, Z)-7, 10, 13-hexadecatrienal, pentadecanal, ( , Z, Z)-2, 4, 7-decatrienal, ( , Z)-2, 6-nonadienal and ( )-2-nonenal have been identified in essential oils from edible seaweeds as characteristic major compounds. The enzymatic formations of the long-chain fatty aldehydes from fatty acids such as linolenic acid, linoleic acid, oleic acid and palmitic acid, respectively, have been demonstrated. Based on enzymatic formation of (2/ )-hydroxy-palmitic acid and 2-oxo-palmitic acid from palmitic acid during biogeneration of pentadecanal and on incubation experiments of synthetic (25)- or (2/ )-hydroxy-palmitic acid and 2-oxo-palmitic acid as substrates with crude enzyme solution of Viva pertusa, the biogeneration mechanism of long chain aldehydes via oxylipins is discussed. 

The following are the principal members of the fatty series erf aldehydes which either occur in essential oils, or are used in synthetic perfumery —... 

Hydroxylamine is used as a reducing agent in many inorganic and organic synthetic reactions. Other applications of this compound include purification of aldehydes and ketones dehairing of hides as an antioxidant for fatty acids to stabilize lower oxidation states of metal ions for analysis and in photography. 

Fatty odors, for example, are effectively masked by citrus notes, especially orange. This is so because the C8 to C12 fatty alcohols and aldehydes, with their distinctly fatty character, are natural components of citrus oils. It is not by chance that cod liver oil, administered to children in former days as a rich source of oil-soluble vitamins, was commonly flavored with orange, and that citrus oils are major components of the Eaux de Cologne used to mask the fatty components of perspiration odor. Synthetic citrus oils in which the fatty aldehydes and alcohols have deliberately been left out are even more effective masking agents. 

Branched chain fatty acids, such as 2-methylpropanoic, and 2-methylbutanoic and 3-methylbutanoic acids, are not products of the fatty acid synthetic pathway. They are instead derived from oxidation of the aldehydes formed from a-keto acids during amino acid metabolism (Fig 8D.5). The mechanism of regulation is not known. 

The broad applicability of the oxo synthesis is reflected by the plethora of substrates which are converted to aldehydes - for instance, diolefins such as butadiene, alkynes [61] or unsaturated fatty acids [66]. Olefinic substrates containing one or more functional groups attract much attention due to the high synthetic value of the resulting aldehyde products. The following examples refer to some relevant publications [63], and in particular to the comprehensive review by Botteghi [49]. For a detailed discussion of particular structures see [4] and [8]. 

The Code mentions 382 synthetic additives, comprizing 69 individual flavouring substances and the following 18 chemical groups ketones, lactones, aromatic aldehydes, aromatic alcohols, esters, ethers, isothiocyanates, indole and its derivatives, fatty acids, aliphatic aldehydes, aliphatic alcohol, aliphatic hydrogen carbide aldehydes, (translation error, probably hydrocarbons), thio alcohols, thio ethers, terpene hydrocarbons, phenols, phenolethers, furfural and its derivatives. 

The finding of formyl-CoA, and not formate, as end-product of the a-oxidation process directly suggested that the second product might be a fatty aldehyde and not a fatty acid as assumed till then. GC-analysis of the lipophilic products formed by peroxisomes incubated with 2-hydroxy-3-metiiylhexadecanoyl-CoA showed an unknown metabolite, co-eluting with synthetic 2-methylpentadecanal. If NAD was present, the aldehyde was converted almost completely into 2-methylpentadecanoic acid, presumably by a peroxisomal aldehyde dehydrogenase. ... 

Undec-lO-enal is a widely employed synthetic aroma compound with a citrus, waxy, fatty odor accompanied by a green, soapy nuance. It can be produced by hydroformylation of 1,9-decadiene (Scheme 6.25). The required substrate is accessible, for example, by olefin disproportionation of cyclooctene with ethylene [100]. The diene was reacted with syngas in the presence of a heterogenized Rh catalyst in a flow reactor to give undec-lO-enal and 2-methyldec-9-enal in 80% overall yield and a slight dominance of the linear aldehyde. The isomers could be separated by distillation. The smell of the branched aldehyde is very similar to that of... 

Aldehydes are more easily identified than are the parent compounds, since a wide range of standards is available from commercial sources or can be prepared synthetically from other lipids. As an example of the full application of this methodology, more than 30 different bases were detected in the sphingolipids of bovine kidney [469]. Mass spectrometry can be utilised as an aid to identification of aldehydes (see also Section B above), although some workers have preferred to reduce them to fatty alcohols and then to prepare acetate or TMS ether derivatives for this purpose [624]. In addition, all the methods for the location of double bonds in fatty acids, such as ozonolysis or hydroxylation with osmium tetroxide and preparation of TMS ethers for MS, have been utilised with aldehydes prepared from sphingoid bases [464,465]. 

Putrefied animal matter hcis formed the basis for coyote attractants of possible value in pest control programs. Thus, a putrefied fish formulation has been used as a coyote lure and, more recently, attention has been directed to a fermented aqueous suspension of chicken whole-egg powder, developed initially as an attractant for flies (48). The odor components csf this material have been subjected to detailed chemical analysis ty Bullard et al. (49) and are reported to include volatile fatty acids (77% total 13 acids identified), bases (13% total, mainly trimethylamine, 9 amines identified), and headspace volatiles, including esters, aldehydes, ketones, alcohols, alkyl aromatics, terpenes and sulfur compounds (10% total, 76 compounds identified). Based on these data, a synthetic mixture, "synthetic fermented egg" has been formulated, composed largely of a mixture of ten volatile fatty acids (81%), together with a diverse range of amines and other compounds (50). This mixture was found to be as attractive to coyotes as the fermented preparation itself. The volatile fatty acid component alone was found to exhibit substantial coyote attractancy also (50,51). ... 

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