8-Decen-10-olide

Additional representatives of six-membered 5-lactones are 5-decalactone 155, constituent of fruits, cheese and dairy products with creamy-coco nut and peachy aroma, jasmolactone 156 as well as 5-2-decenolactone (2-decen-5-olide) 157 (Structure 4.47). 

The closely related 5-decanolide (5-decalactone), not only found in many fruits but also found in dairy products, exhibits a creamy-coconut, peach-like aroma [49] and can be synthesised from the corresponding a,(3-unsaturated lactone 2-decen-5-olide found in concentrations of up to 80% in Massoi bark oil using basidiomycetes or baker s yeast [229]. After about 16 h of fermentation, 1.2 g 5-decanolide was obtained. At the same time, the minor lactone in... 

Jasmine Jasminum grandiflorum Benzyl acetate, (S)-linalool, indole, (Z)-jasmone (27), (R,Z)-7-decen-5-olide (28), methyl (+)-ep/-jasmonate (29) 95,96,98... 

Decen-4-olide Densipolic acid Sporobolomyces odoms Fatty, buttery, nutty... 

These terpene notes are supported by (Z)-3-hexenol, (E)-2-hexenal, (E)-2-hexenol with their fresh, green character. Gamma- and delta-lactones (4-decanolide, 5-decan-olide, 4-dodecanolide, 5-dodecanolide-(Z)-7-decen-5-olide) impart the sweet, creamy, buttery, peach and apricot character. 2,5-Dimethyl-4-hydroxy-furan-3(2H)-one and 2,5-dimethyl-4-methoxy-furan-3(2H)-one are responsible for the sweet creamy fruity body. A bouquet of esters imparts the overall fruity character (mainly esters of ethyl-, (Z)-3-hexenyl and butyl alcohol with acetic-, butanoic-, 2-butenoic, 3-hydroxybutanoic- and hexanoic acid). 

Heinzer, F., Soukup, M., and Eschenmoser, A. (1978) Uber 3,3,6,9,9-pentamethyl-2,10-diaza-bicyclo[4.4.0]-l-decen und einige seiner derivate. Helvetica Chimica Acta, 61, 2851-2874 Sternbach, D., Shibuya, M., Jaishi, F. et al. (1979) A fragmentational approach to macrolides (5- ,8-Z)-6-methyl-5,8-undecadien-l 1-olide. Angewandte Chemie — International Edition, 18, 634-636. 

Jasminfe) lactone [(Z)-7-decen-5-olide, jasmolac-tone]. 

Camphanic acid, T"4.2 2-Ethyl-5-hydroxy-4,5-dimethylhex-2-ene-l,6-dioic acid lactone, K"8.9 Intergerrinedc acid lactone, K"8.12 8-Hydroxy-4-oxo-6-decen-9-olide, Y"11.2... 

Hydroxy-7-decen-5-yn-4-olide, see D-30108 13-Hydroxy-7,l 1-dehydromatrine, in L-10040 8a-Hydroxydehydrozaluzanin C, in D-10175 12a-Hydroxy-13,18-dehyroparain, in N-10025 1-Hydroxydelobanone, see D-20093... 

In addition to the 5-lactones of structure (41), other lactonic aroma components with a saturated ring are known, the structure of which, however, is somewhat different from that of the n-series represented by (41). These are 6-hydroxy-5-hexanolide (42), identified in tomato (557), and three cyclic compounds carrying an unsaturated chain in position 5, viz. (Z)-7-decen-5-olide (jasmine lactone) (44) 712), identified in the flavor of black tea (50) together with methyl jasmonate (779). (Z)-9-dodecen-5-olide (45) and (Z)-9-tetradecen-5-olide (46), the latter two lactones having been isolated from butter flavor (50, 725). On the other hand, lactone (43) was isolated from milk where it is present in a quantity of 10 pg/kg (0.001 ppb) (247) this quantity, however, is probably much lower than the threshold value. 

It is interesting that the 8-decalactone is formed by an entirely different biotrans-fonnation. This lactone is formed by the miCTobial reduction of an a,P-unsaturated lactone found in Massoia bark oil. Massoia bark oil contains about 80% 2-decen-5-ohde, 1% 2-dodecen-5-olide and 6% benzyl benzoate. Several microorganisms... 

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