Aliphatic lactones

Solid-phase extraction procedures and quantitative analysis of aliphatic lactones in wine were described by Ferreira et al. [32] dealing with, among others, the quantitation of y-nonalactone and y-undecalactone at trace levels. 

Ferreira V, Jarauta I, Ortega L, Cacho J (2004) Simple strategy for the optimization of solid-phase extraction procedures through the use of solid-liquid distribution coefficients—application to the determination of aliphatic lactones in wine. J Chromatogr A 1025 147 Rettinger K, Karl V, Schmarr HG, Dettmar F, Hener U, Mosandl A (1991) Chirospecific analysis of 2-alkylbranched alcohols, -acids, and -esters chirality evaluation of 2-methylbutanoates from apples and pineapples. Phytochem Anal 2 184... 

Hydroxyundecanoic acid lactone) (aliphatic lactone) Prunus persica (peach) (Rosaceae) [fruit] ... 

TABLE 11. Amounts of y- and s-Aliphatic Lactones Isolated from Butter Fat (ppm) (2, 28, 29). 

T.J. Siek, J.A. Albin, L.A. Sather and R.C. Lindsay. Comparison of flavor thresholds of aliphatic lactones with those of fatty acids, esters, aldehydes, alcohols and ketones. J. Dairy Sci., M, 1-4 (1971). 

Paraoxonase enzymes clearly belong to a distinct enzyme family.11,19 They are not serine or cysteine proteases but instead use divalent metal ion for catalysis. The enzymes have limited substrate specificity but do hydrolyze a variety of aromatic and aliphatic lactones, including several statin lactones.20... 

Since the publication of this work Aharoni et al., it has been established that serum paraoxonase (PON1) is a lipo-lactonase, and its preferred substrates are five- and six-membered ring lactones, typically with aliphatic side chains.° °°° °° In the original article, data for trade-offs with the native activity were presented with both the aromatic lactone dihydrocoumarin, and aliphatic lactones. However, more recent works indicated that dihydrocoumarin does not bind PON1 s active site in the same mode as aliphatic lactones.°° "° Thus, the trade-offs presented here are the average values of two aliphatic lactones (i5-valerolactone and and 7-heptanolide). 

In 1998, Abbott (6A01) described the results of the examination of numerous food additives by the World Health Organization. The food additives in this particular study comprised a series of so-called aliphatic lactones. Among the lactones discussed were several that not only are used as foodstuff additives but also occur in tobacco and/or its smoke and several that are used as tobacco additives. The results of several toxicological studies (acute toxicity, short-and long-term toxicity, carcinogenicity) and genotoxic studies on the lactones were described in detail by Abbott. Table Vl-1 presents the results listed by Abbott on those lactones that are used in tobacco products. 

Bal Ischmiester and Dereksen ( ) reported nine alcohols isolated from a steam distillate of peanuts. Brown et al. (62) resolved extracts from roasted peanuts into various fractions via classical chemical techniques. A number of acids were found, including acetic, propionic, isobuyric, isovaleric, valeric, heptanoic, decanoic, lauric, myristic, phenylacetic, and dihy-droxynapthaleneacetic. Carbonyl compounds reported were hexanal, 2, 4-decadienal, and 2-oxooctanal. Tentative evidence was presented for aliphatic lactones, which are powerful flavoring agents. 

In another paper by Albrecht et aL, [48] the biosynthetic pathway involved in the production of aliphatic lactones was studied. In particular, the study was focused on the mechanism of the biotransformation of Sy and (7 yS)-13-hydroxy-(Z,A)-9,ll-octadecadienoic acid into the optically pure (/ )- -decalactone by the yeast Sporobolomyces odorus. For this purpose, deuterium-containing derivatives of coriolic acid needed to be synthesized. Figure 10 shows the synthetic approach chosen by the authors to produce 13-HSA-13-J and 13-HSA-9,10,11,12- 4 starting from linoleic acid. 

The importance of aliphatic lactones as aroma components in foods is based on their characteristic organoleptic properties. Due to their mostly low odor thresholds averaging about 0.1 ppm (572), lactones often have a high flavor value. Detailed reports 128, 162, 425, 688) exist on the formation of lactones, especially from glycerides, higher fatty acids and short-chain functionalized aliphatic compounds as their precursors. Whereas y-lactones preferentially occur in plants, 5-lactones are mainly found in animal products. Thus, considerable quantities of 5-lactones... 

Boldingh, j., and R. J. Taylor Trace Constituents of Butterfat. IV. Isolation and Identification of Unsaturated Aliphatic Lactones. Nature 194, 909 (1962). 

Dimick, P. S., N. J. Walker, and S. Patton Occurrence and Biochemical Origin of Aliphatic Lactones in Milk Fat — A Review. J. Agric. Food Chem. 17, 649 (1969). 

SiEK, T. J., J. A. Albin, L. A. Sather, and R. C. Lindsay Comparison of Flavor Thresholds of Aliphatic Lactones with Those of Fatty Acids, Esters, Aldehydes, Alcohols and Ketones. J. Dairy Sci. 54, 1 (1971). 

Aliphatic esters weak, tendency to protonate Aliphatic lactones medium to weak, tendency to protonate... 

Molecular ion Usually of low intensity and easily protonated to [M+H]+ in aliphatic lactones abundant in the case of aromatic lactones. 

Aliphatic lactones are important as aroma components in foods and flavors. Among them, y-lactones preferentially occur in plants and J-lactones are mainly found in animal products. The details on naturally-occurring lactones as aroma components are described in the literature (87). It is interesting that quercus lac-tone-a (1) and -b (2), two diastereomeric branched nonlactones, have been detected as ingredients in aged whiskeys (88, 134). These lactones were isolated from woods of some Quercus species which are widely used to make barrels for aging spirits such as whisky and brandy (72, 73). 

Besides siloxane copolymers, poly(phenylene oxide)/PCs, epoxide/PCs, polyimidecarbonates," polyamidecarbo-nates, polyurethanecarbonates," and copolymers with aliphatic lactones such as pivalactone and CL were also reported. ... 

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