86252-65-5

Usage

Uses

Used in Pest Control Industry:
(E,Z)-2,13-Octadecadienyl acetate is used as a pheromone-based pest control agent for managing populations of the moth Synanthedon tenuis. By mimicking the natural sex pheromone of the female moth, it attracts male moths and disrupts their mating behavior, thereby reducing the overall population of the pest. This approach is considered environmentally friendly and targets specific pests without harming non-target species.
Used in Chemical Ecology Research:
(E,Z)-2,13-Octadecadienyl acetate is also used as a research tool in the field of chemical ecology. It helps scientists understand the complex chemical communication systems used by insects for mating, foraging, and other social behaviors. Studying the structure and function of (E,Z)-2,13-Octadecadienyl acetate can provide insights into the development of novel pest control strategies and the broader implications of chemical signaling in ecosystems.
Used in Fragrance Industry:
Although not explicitly mentioned in the provided materials, (E,Z)-2,13-Octadecadienyl acetate may also have potential applications in the fragrance industry due to its unique chemical structure and biological activity. Its ability to attract insects could be harnessed to create natural and effective insect repellents or attractants for various purposes, such as pest control or agricultural applications. However, further research and development would be required to explore these potential uses fully.

InChI:InChI=1/C20H36O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-20(2)21/h6-7,17-18H,3-5,8-16,19H2,1-2H3/b7-6-,18-17-

Upstream product

• 2774-84-7 undec-10-yn-1-ol 
• 86252-57-5 15-bromopentadec-5-yne 
• 64437-42-9 (10Z)-10-pentadecen-1-ol 
• 92210-93-0 1-bromo-(Z)-10-pentadecene 
• 123551-46-2 octadec-cis-13-en-2-yne-1-ol 
• 126126-88-3 1-tetrahydropyranyloxy-octadec-7-yn-13Z-ene 
• 51953-88-9 1-[(tetrahydropyran-2-yl)oxy]undec-10-yne 
• 34683-71-1 undec-2-yn-1-ol 
• 928342-58-9 C₁₅H₂₇I 
• 86252-61-1 Acetic acid octadeca-2,13-diynyl ester 
• 108-24-7 acetic anhydride 
• 131335-41-6 (2Z,13Z)-2,13-octadecadien-1-ol 
• 164414-91-9 1-tetrahydropyranyloxy-2,13-octadecadiyne 
• 72032-18-9 2-Pentadec-10-ynyloxy-tetrahydro-pyran 

Downstream Products

• 86252-74-6 (2E,13Z)-octadeca-2,13-dienyl acetate 

Relevant academic research and scientific papers

Synthesis and characterization of 3,13- and 2,13-octadecadienyl compounds for identification of the sex pheromone secreted by a clearwing moth, Nokona pernix

Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M - 18]+ at m/z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.

A CONVENIENT SYNTHESIS OF 2,13- AND 3,13-OCTADECADIENYL ACETATES, SEX PHEROMONE COMPONENTS OF THE Synanthedon SPECIES

The sex pheromone components of several Synanthedon species, 2,13- and 3,13- octadecadienyl acetates (Ic, Id, IIc, IId), have been synthesized following the acetylenic route of chain elongation.Starting from ω-alkyn-1-ols III, the final compounds were constructed in five steps in about 30percent overall yields.Transformation of triple bond containing intermediates into the corresponding (Z)- and (E)-olefins was achieved either by hydrogenation over the P2-Ni catalyst or by using a dispersion of sodium in toluene.The title pheromones were generated in more than 97percent stereoisomeric purity. 1H and 13C NMR data of all derivatives are included.

(E,Z)-2,13-OCTADECADIEN-1-OL ACETATE. A NEW FEROMONE STRUCTURE FOR SESIID MOTHS

(E,Z)-2,13-Octadecadien-1-ol acetate was identified from ovipositor extracts of the grape root borer and was shown to attract males of the species.