53120-27-7

Usage

Uses

Used in Pheromone-based Insect Control:
Z,Z-3,13-OCTADECADIENYLACETATE is used as a behavioral antagonist for Synanthedon tipuliformis males. It is employed in pheromone-based insect control strategies to disrupt the mating process and reduce the population of these insects. By mimicking the natural sex pheromone of the female insects, it attracts the male counterparts and diverts them from finding actual mates, thereby decreasing the chances of successful reproduction.
Used in Agricultural and Environmental Management:
In the agricultural industry, Z,Z-3,13-OCTADECADIENYLACETATE is used as a part of integrated pest management (IPM) strategies. It helps in controlling the population of pest insects, such as Synanthedon tipuliformis, without causing harm to the environment or non-target species. This approach is more sustainable and eco-friendly compared to traditional chemical pesticides.
Used in Research and Development:
Z,Z-3,13-OCTADECADIENYLACETATE is also used in research and development for understanding insect behavior, communication, and mating patterns. It aids scientists in studying the effects of pheromones on insect populations and developing new strategies for pest control and management.
Used in Wildlife Conservation:
In the field of wildlife conservation, Z,Z-3,13-OCTADECADIENYLACETATE can be employed to protect endangered species from being affected by invasive insect species. By controlling the population of harmful insects, it helps in maintaining the balance of the ecosystem and preserving the natural habitats of various species.

Safety Profile

Low toxicity by ingestion. Whenheated to decomposition it emits acrid smoke andirritating vapors.

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/h6-7,16-17H,3-5,8-15,18-19H2,1-2H3/b7-6-,17-16-

Upstream product

• 18545-28-3 3-acetoxypropanal 
• 92210-94-1 10(Z)-pentadecen-1-yltriphenylphosphonium bromide 
• 66410-23-9 3,13-octadecadiin-1-ol 
• 108-24-7 acetic anhydride 
• 66410-24-0 (3Z,13Z)-3,13-octadecadienyl alcohol 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 954147-90-1 3,13-octadecadien-1-ol 
• 17689-03-1 1-hexynyllithium 
• 110-53-2 1-Bromopentane 
• 29541-98-8 pentylidenetriphenylphosphorane 
• 66410-27-3 (Z)-13-octadecen-3-yn-1-ol 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 81216-13-9 8-bromooct-1-yne 

Downstream Products

• 66410-24-0 (3Z,13Z)-3,13-octadecadienyl alcohol 

Relevant academic research and scientific papers

Method for preparation of Octadecadienyl acetate as major sex pheromone of cherry tree borer, Synanthedon bicingulate

The present invention relates to a method for producing a sex pheromone of cherry tree borer (Synanthedon bicingulata) in an attempt to control the same. More specifically, provided is a method for stereoselectively producing high purity (3E,13Z)- octadecadienyl acetate and (3Z,13Z)-octadecadienyl acetate respectively which are major sex pheromones of cherry tree borer from a cheap starting material in an efficient, simple, and economically feasible way.COPYRIGHT KIPO 2018

Sequential alkynylation of ω-bromoalkyl triflates: Facile access to unsymmetrical non-conjugated diynes including precursors to diene pheromones

Sequential treatment of ω-bromoalkyl triflates with an alkynyllithium at 0°C followed by addition of a second alkynyllithium and NaI and heating the reaction mixture provides a simple one-pot access to unsymmetrical diynes in good yields. These diynes may be transformed stereoselectively into diene pheromones such as (Z,Z)- and (E,Z)-3,13-octadecadienyl acetate. Graphical Abstract

Synthesis of (3Z,13Z)-3,13-octadecadienyl acetate - Sex pheromone of Synanthedon tenuis-using readily available C11-synthon

Synthesis of (3Z,13Z)-3,13-octadecadienyl acetate has been achieved from the readily available 10-undecen-1-ol using cheaper reagents and less number of steps. In the key step alkylation of an alkyne is performed with solid sodamide giving the product in 50% yield. The method can be easily scaled-up.

Method for the preparation of an alkynyl compound

A novel and efficient method is proposed for the synthetic preparation of a long-chain alkynyl compound in a one-pot reaction without isolating the intermediate from the reaction mixture. The inventive method comprises the steps of: (a) a Grignard coupling reaction of an ω-halogeno-1-alkynyl magnesium halide compound of the general formula X1 MgC C(CH2)n X2, in which X1 is a halogen atom, X2 is an atom of Br or I and n is 3 to 10, and a Grignard reagent of the general formula RMgX1, in which R is a group selected from the class consisting of alkyl groups, alkenyl groups, alkynyl groups, alkapolyenyl groups, aryl groups and hydrocarbon groups having protected hydroxy group to give an intermediate compound of the general formula X1 MgC C(CH2)n R; (b) subjecting the intermediate compound to a reaction with a reactant selected from the class consisting of C2 -synthons, C1 -synthons and chlorosilane compounds having reactivity with the intermediate compound at the X1 Mg-terminal; and (c) hydrolyzing the reaction product obtained in step (b).

Stereoselective synthesis of (Z,Z)-3, 13-octadecadien-1-ol, (Z,Z)-3, 13-octadecadien-1-yl acetate and their (E,Z)isomers

(Z,Z)-3,13-Octadecadien-1-ol (VIII), (Z,Z)-3,13-octadecadien-1-yl acetate (IX) and their corresponding (E,Z) isomers (X and XI) have been synthesized via Li2CuCl4 catalysed coupling reaction of (Z)-8-tridecylmagnesium bromide with mesylate (II) as a key step.

1,(ω-1)-Dienes: solvent controlled unilateral or bilateral metallation

In hexane, i.e. under heterogeneous conditions, 1,(ω-1)-dienes readily undergo double deprotonation to give bis(allylmetal) intermediates.In tetrahydrofuran at -75 or -50 deg C, however, only monometallation occurs with dienes having chains of up to 12 carbon atoms.The practical potential of such selective monosubstitution reactions is demonstrated by two novel pheromone syntheses.

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.