4-Tetradecen-14-olide

Z) 5 Tetradecen 4 olide (sex pheromone of female Japanese beetle)... 

Notice that (Z) 5 tetradecen 4 olide IS a cyclic ester Recall from Section 19 15 that cyclic esters are called lactones and that the suffix olide is char acteristic of lUPAC names for lactones... 

Enantiomerically pure japonilure [(4JR,5Z)-5-tetradecen-4-olide, 26] is commercially important to attract the Japanese beetle (Popillia japonica), because only pure (4.R,5Z)-26 is bioactive, while ( )-26 is totally inactive. Synthesis of (4 ,5Z)-26 via enzymatic resolution of racemic intermediates was first reported by Sugai [63], and then further studied by Fukusaki [64] to establish the process as summarized in Scheme 39. Lipase PS (Amano) from Pseudomonas sp. and lipase OF (Meito) from Candida cylindracea were shown to be the enzymes of choice. 

Notice that (/ )-(Z)-5-tetradecen-4-olide is a cyciic ester. Recaii from Section 18.15 that cyciic esters are caiied lactones and that the suffix -olide is characteristic of iUPAC names for iactones. 

Advent of ring-closing olefin metathesis reaction has influenced the synthetic strategy of pheromones very much. For example, the racemate of a macrolide pheromone such as (5Z,13S)-5-tetradecen-13-olide (29) (aggregation pheromone of the flat grain beetle, Cryptolestes pusillus) could readily be synthesized as shown in Scheme 42 [67]. Unfortunately, ( )-29 prepared by this method was a mixture of c/s, trans-isomers (Z/E=69 31). (S)-5-Hexadecanolide (27) was also synthesized by means of ring-closing olefin metathesis as shown in Scheme 43 [68]. 

Japonilure R), the sex pheromone of the female Japanese beetle. Papilla japonica and its enantiomer, (5)-(+)-(5Z )-tetradecen-4-olide, which is the pheromone of the Osaka beetle, Anomala osakana have been synthesized using a highly convergent procedure and in satisfactory overall yields. 

The constituents responsible for the musk odor of the oil are (Z)-7-hexadecen-16-olide [123-69-3] (ambrettolide) and (Z)-5-tetradecen-14-olide [63958-52-1]. ... 

Ambrette seed Hibiscus abelmoschus L. (Z)-7-Hexadecan-16-olide, ambret-tolide (8-9), 5-tetradecen-14-olide, (2f ,6f )-farnesyl acetate (39-59)... 

Z.13S)-5- Tetradecen-13- olide S Flat grain beetle Cryptnlestes pusiUus) A Grubbs Olefin methatesis [155]... 

A 15-membered ring macrolide, 4-tetradecen-14-olide (Fig. 32,185), has been reported as an anal sac secretion of striped hyena Hyaena hyaena, and it may be used to mark territorial boundaries [204]. Ambrettolide (130) is a 17-membered ring macrolide produced by plants and insects (see Sections V.B and VI.A). It is also detected in the lipid from musk of muskrat Ondatra zibethica [205]. 

Maurer, B., and Grieder, A. (1977). (Z)-5-Tetradecen-14-olide, a new macrocyclic lactone, and two unsaturated straight chain acetates from ambrette seed absolute. Helv. Chim. Acta 60, 1155-1160. 

Simple, acid-catalysed dehydration of an >-hydroxy-acid under conditions of high dilution has been used in a synthesis of the expensive perfumery ingredient (Z)-5-tetradecen-14-olide, and also in the final step of a synthesis of ( )-decamine/ °... 

Metab. of C. piceae. [ag +23.8 (e, 0.34 in CHCI3). 4-Deoxy, 3,4-didehydro [154878-77-0]. 5,6-Dihydro-6-nonyl-2H-pyran-2-one, 2- Tetradecen-5-olide... 

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. 

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