Dodecenyl acetate

Rasmussen, L.E.L. (2001) Source and cyclic release pattern of Z-7-dodecenyl acetate, the preovulatory pheromone of the female Asian elephant. Chem. Senses 26, 611-623. 

The female elephant pheromone (Z)-7-dodecenyl acetate occurs bound to urinary proteins. When it is taken up by a male elephant, the acetate is bound to proteins of the trunk mucus. This might facilitate transport of the pheromone to the vicinity of the sensory epithelium of the vomeronasal organ (Rasmussen and Schulte, 1998). 

The sex pheromone emitted by the female yellow mealworm beetles, Tenebrio molitor L. (Coleoptera Tenebrionidae), 4-methyl-1-nonanal is well known. However, it was observed that males emit a pheromone that attracts females, which was identified as (Z )-3-dodecenyl acetate. 

A combination of (.Z)-8-dodecenyl acetate and ( )-8-dodecenol was identified from the sex pheromones glands of the carambola fruit borer, Eucosma notanthes Meyrick (Lepidoptera Tortricidae). The ratio of the alcohol to the ester in the extracts was 2 7. GC, GC-MS, chemical deriva-tization, and comparison of retention times with authentic standards were used for identification. ... 

The sex pheromones of four Plusiinae species in the family Noctu-idae namely, Ctenoplusia albostriata (CA), Macdunnoughiapurissima (MP), Syngrapha ain (SA) and Diachrysia stenochrysis (DS), were identified. CA females produced ( )-5-decenyl acetate (1), ( )-7-dodecenyl acetate (II), and (.Z)-7-dodecen-l-ol (III) in a ratio of 2 100 13. The MP females produce II, III, and ( )-5-dodecenyl acetate (IV) in a ratio of 100 80 20. Compounds 11 and 111 were also identified from the SA females, whereas the DS females produced just one active compound, (.Z)-7-decenyl acetate. DS species were the first Plusiinae species identified using only the oo3-compound and none of the oo5-compounds, such as II and III that are common components of Plusiinae pheromones. 

Analyses of the pheromone glands of the kvoAcAnadevidiapeponis and Maddunnoughia confusa, showed that A. peponis produces six monoene acetates and two monoene alcohols and that M. confusa produces five monoene acetates. These components include (2 )-7-dodecenyl acetate as a major common constituent and three other acetates as minor common constituents. The minor constituents are quite different in blend composition. An indispensable component for male attraction is (Z )-5-decenyl acetate... 

Fig. 8.2. Geographic variation in male attraction to pheromone in the turnip moth, Agrotis segetum as percentage capture at 11 localities in Eurasia and Africa. The numbers above each column indicate the highest catch of the best lure. Z5, (Z)-5-decenyl acetate Z7, (Z)-7-dodecenyl acetate and Z9, (Z)-9-tetradecenyl acetate. Within each diagram, differing letters indicated = 0.05. (FromToth et al, 1992.)...

Z)-8-dodecenyl acetate [28079-04-1] CH3(CH2)2CH=CH(CH2)7OOCCH3 oriental fruitmoth, Gmpholitha molesta... 

Z)-9-dodecenyl acetate [16974-11-1] CH3CH2CH=CH(CH2)8OOCCH3 grape berry moth, Paralobesia viteana (with (E)-isomer)... 

Jones I. F. and Berger R. S. (1978) Incorporation of [1-14C]acetate into cis-7-dodecenyl acetate, a sex pheromone in the cabbage looper Trichoplusia ni. Environ. Entomol. 7, 666-669. 

Grapholitha molesta (22). Females of this species emit (Zj-8-dodecenyl acetate as a major sex pheromone component, along with a synercjist, dodecyl alcohol (23). Addition of the (E)-isomer of 8-dodecenyl acetate increased male catches about 25-fold maximum attractiveness occurred with about 8% of this isomer. 

Tertiary pheromonal blends have been identified in two noctuid moths. The red bollworm, Diparopsis castanea, emits dodecyl acetate, (E)-9-dodecenyl acetate, 11-dodecenyl acetate, and (E)-9,ll-dodecadienyl acetate as a sex pheromone, whereas Spodoptera littoral is utilizes a blend made up of tetradecyl acetate, (E)-9-tetradecenyl acetate, (E)-ll-tetradecenyl acetate, and (Z,E)-9,ll-tetradecadieny1 acetate (89). For both species, the conjugated dienes are the most potent olfactory stimulants. 

Another important result was obtained from in vivo experiments using the cabbage looper moth (CL), Trichoplusia ni (11). The biosynthetic pathway postulated for this insect is given in Fig 2. Substrates were applied to the gland and the (Z)-7-dodecenyl acetate isolated, cleaved at the double bond by ozonolysis, and the products isolated as benzyloximes. When acetate was used as substrate, radioactivity appeared in both products, but when hexadecanoic acid tritiated at the 16 position was used, radioactivity only appeared in the fragment derived from the terminal carbons. This demonstrated that incorporation took place as proposed in Fig 2, not by some scheme involving degradation and resynthesis. 

Until the above research had been conducted, (Z)-7-dodecenyl acetate was the sole identified pheromone component. This compound was an effective attractant for males, but insects did not perform the complete range of behaviors that were exhibited in response to females. The additional components identified by Bjostad et al. (1) were found only after studies on biochemical precursors were... 

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