55774-32-8

Usage

Uses

Used in Pheromone Applications:
TRANS-7, CIS-9-DODECADIENYL ACETATE is used as a pheromone for the trapping and control of the European grapevine moth (Lubesia butrana). This application takes advantage of the compound's ability to mimic the natural pheromones produced by the moth, attracting males and disrupting their mating behavior, thus helping to control the population of this pest.
Used in Chemical Industry:
In the chemical industry, TRANS-7, CIS-9-DODECADIENYL ACETATE can be used as a building block or intermediate in the synthesis of various compounds, such as fragrances, flavors, and other specialty chemicals. Its unique structure and functional groups make it a valuable component in the development of new products with specific properties and applications.
Used in Research and Development:
TRANS-7, CIS-9-DODECADIENYL ACETATE can also be utilized in research and development for studying its chemical properties, reactivity, and potential applications in various fields. This may include exploring its use in materials science, pharmaceuticals, or other areas where novel compounds with unique properties are sought after.

Metabolic pathway

Facile hydrolysis to the alcohol (2) would be expected in alkaline solution. No published information is available but generally compounds of this class are rapidly degraded biologically and their behaviour is similar to that of typical long chain alkenoic acids.

Degradation

The effect of heat, sunlight, radicals and oxidants on isomerisation of the double bonds has been investigated. The compound is degraded by heating at 50 °C (6 mg remained of 100 mg after 6 days) but the process may be slowed by the addition of antioxidants. Isomerisation occurs readily in sunlight in the presence of a photosensitiser. Within 100 minutes an equilibrium mixture containing 76% E,E and 12-14% of each of the E,Z- and Z,E-isomers was formed. In the absence of photosensitiser, degradation was faster than photoequilibration. Photo-oxidation in the presence of Rose Bengal as a singlet oxygen generator gave a furan derivative (4) (see Scheme 1). This takes place after isomerisation of 1 to the E,E-isomer (3) (Shani et al., 1981).

InChI:InChI=1/C14H24O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h4-7H,3,8-13H2,1-2H3/b5-4+,7-6-

Upstream product

• 108-24-7 acetic anhydride 
• 66471-35-0 (7Z,9E)-7,9-dodecadien-1-ol 
• 50375-98-9 (Z)-2-pentenylidene triphenylphosphorane 
• 113093-78-0 7-tert.butoxy-heptanal 
• 99393-41-6 (Z)-9-Dodecen-7-ynyl acetate 
• 113093-77-9 7-tert-Butoxy-1,1-diethoxy-heptane 
• 58766-03-3 1-(tetrahydro-2H-pyran-2-yl)oxy-7,9-dodecadiene 
• 154556-91-9 (7E,9Z)-dodec-7,9-dien-1-ol 
• 179331-79-4 (3Z,5Z)-3,5-octadienyl tosylate 
• 67818-18-2 (2Z,4Z)-1-acetoxy-2,4-heptadiene 
• 179331-80-7 (3Z,5Z)-1-bromo-3,5-octadiene 
• 179331-78-3 (2Z,4Z)-2,4-heptadien-1-ol 
• 120569-51-9 hepta-2,4-diyn-1-ol 
• 10160-11-9 3,5-octadiyn-1-ol 

Relevant academic research and scientific papers

METHOD FOR PRODUCING COMPOUND HAVING CONJUGATED DIENE STRUCTURE

PROBLEM TO BE SOLVED: To provide a method capable of industrially producing a conjugated diene or a conjugated triene in a short process from a raw material which is easy to obtain and handle. SOLUTION: A conjugated diene is produced from a 3-alkenal via reactions of the following first step, second step, and third step in this order: the first step of reacting a Grignard reagent with the 3-alkenal to obtain a homoallylic alcohol; a second step of reacting an esterification reagent or a halogenation reagent with the homoallylic alcohol to obtain a sulfonic ester or a halogenated product; and a third step of having a base act on the sulfinic acid ester or the halogenated product to cause an elimination reaction. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Olefinic acetates, Δ-9,11-14:OAc and Δ-7,9-12:OAc used as sex pheromone components in three geometrid moths, Idaea aversata, I. straminata, and I. biselata (Geometridae, Lepidoptera)

Pheromone compounds so far identified from most geometrid moths consist of all-Z diene, triene, or tetraene hydrocarbons with chain lengths of C17 to C21, and their monoepoxide derivatives biosynthesized from linoleic and linolenic acids. The present study reports the occurrence of olefinic acetates as sex pheromones in three species of Geometridae. (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate found in female gland extracts of Idaea aversata elicited significant responses from conspecific male antennae in gas chromatography with electroantennographic detection (GC-EAD). In extracts of I. straminata, (Z,E)-7,9-dodecadienyl acetate, (E,Z)-7,9-dodecadienyl acetate, and (Z,Z)-7,9-dodecadienyl acetate were found, and the synthetic compounds elicited strong responses from conspecific male antennae. In the third species, I. biselata, only (Z,Z)-7,9- dodecadienyl acetate was found in the female extracts, and this compound elicited a strong EAD response from the conspecific male antenna. The identities of the pheromone components in I. aversata and I. straminata were further confirmed according to their characteristic ions after GC-MS analyses. Single sensillum recordings from I. aversata showed two types of pheromone-detecting sensilla present on the male antenna. One type contained two receptor neurons, one of which was specifically tuned to (Z,Z)-9,11- tetradecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. A second type contained one neuron responding to (Z,Z)-7,9-dodecadienyl acetate. The two types were clearly different also with respect to external morphology, the former being considerably longer and having a larger base diameter. Also in I. straminata two physiological types of sensilla could be distinguished. One type contained two neurons, one of which responded to (Z,Z)-7,9-dodecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. The second type contained one neuron, responding the (Z,Z)-7,9- dodecadienyl acetate. No correlation between external morphology and physiological response of the investigated sensilla was observed in I. straminata. In field tests, a two-component blend containing (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate in a ratio of 10:1 was attractive to males of I. aversata. This two-component blend was also attractive to males of I. straminata, but in a ratio of 1:1. High numbers of male I. biselata were caught in traps baited with (Z,Z)-7,9-dodecadienyl acetate alone. The incorporation of deuterium labels into pheromone components after topical application of deuterium-labeled palmitic acid confirmed that the pheromone components of I. aversata could be synthesized from this precursor, as has been previously observed for acetate pheromone components of many other moth species. Our results suggest that an evolutionary reversal back to the production of palmitic acid-derived pheromone components has occurred within the geometrid subfamily Sterrhinae.

Synthesis of (7Z,9Z)-dodecadienyl acetate, a component of sex pheromones of the leafrollers Epinotia and Eucosma, using conjugated diynols

Two analogous routes to the title pheromones were elaborated based on organocuprate cross-coupling of Z,Z-dienic electrophiles, (2Z,4Z)-1-acetoxy-2,4-heptadiene (6) and (3Z,5Z)-1-bromoctadiene (8), with ω-tert-butoxy-1-chloropentane and -butane, respectively.Optimal conditions for the reaction of 2,4-heptadiyn-1-ol and 3,5-octadiyn-1-ol to the respective Z,Z-alkadienols as precursors for the electrophiles were found.Treatment of diynols with activated zinc in aqueous alcohol provided high geometrical purity of the product (> 94percent).In both cases, copper-catalyzed cross-coupling afforded 1-tert-butoxy-7,9-dodecadiene (four stereoisomers), acetolysis of which gave the target pheromone contaminated by stereoisomers.In the case of allylic electrophile 6, the reaction occured with the loss of the initial configurational purity, whereas the use of homoyllylic bromide 8 ensured almost complete retention of the configuration of the double bonds and obtaining the target pheromone of 87percent configurational purity.

Exo- and Endohormones. X. A Novel Route to an Isomer Mixture of 7,9-Dodecadien-1-yl Acetate Utilizable in Field Attraction of Lobesia botrana Males

Wittig condensation of (Z)-2-pentenylidene triphenylphosphorane (14) and 7-tert.-butoxy-heptanal (13) under conditions of phase transfer catalysis and subsequent conversion into the corresponding acetate afforded a mixture of 28percent 7(E),9(Z)-dodecadien-1-yl acetate, the sex pheromone of Lobesia botrana, along with the other geometrical isomers and 30percent unidentified by-products.The synthons 14 and 13 were prepared starting with (Z)-2-butene-1,4-diol (1) and hexane-1,6-diol (9), respectively.

Mass Spectra of Dodecadienic Compounds with a Conjugated Double Bond, Lepidopterous Sex Pheromones

All geometrical isomers of 5,7-, 6,8-, 7,9-, 8,10- and 9,11-dodecadien-1-ols, and their acetates and aldehyde derivatives were analyzed by electron impact mass spectrometry.The abundance of molecular ion (M(1+)) was observed in every spectrum, and the relative intensity of M(1+) tended to be strong if the compound possessed an (E)-double bond(s).In addition to M(1+), (1+) (alcohols) and (1+) (acetates), every dienic compound showed typical series of CnH(2n-2)(1+)CnH(2n-5)(1+) with abundance maxima around C4, C5, C6 or C7.Each double bond positional isomer characteristically yielded different ion peaks in the series, which were useful for its distinction from other isomers.These results indicate that the chemical structure of a natural pheromone of Lepidoptera is easily deduced successfully by GC-MS analysis if it is a conjugated dienic pheromone.