57981-60-9

Basic information

• Product Name: (Z,E)-trideca-4,7-dien-1-yl acetate
• Synonyms: (Z,E)-trideca-4,7-dien-1-yl acetate;(E,Z)-4,7-Tridecadienyl acetate;Einecs 261-058-2;(4E,7Z)-deca-4,7-dienyl acetate;4,7-Tridecadien-1-ol,1-acetate, (4E,7Z)-;4E7Z-13Ac
• CAS NO: 57981-60-9
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.36574
• EINECS: 261-058-2
• Mol File: 57981-60-9.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 302.2°Cat760mmHg
• Flash Point: 91°C
• Appearance: /
• Density: 0.893g/cm³
• Vapor Pressure: 0.00101mmHg at 25°C
• Refractive Index: 1.462
• CAS DataBase Reference: (Z,E)-trideca-4,7-dien-1-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (Z,E)-trideca-4,7-dien-1-yl acetate(57981-60-9)
• EPA Substance Registry System: (Z,E)-trideca-4,7-dien-1-yl acetate(57981-60-9)

Safety Data

• Hazardous Substances Data: 57981-60-9(Hazardous Substances Data)

Usage

Description

(Z,E)-trideca-4,7-dien-1-yl acetate, also known as (E,Z)-4,7-Tridecadienyl acetate, is a chemical compound that serves as the major component of sex pheromones in the potato tuber moth. It is characterized by its distinct structure, featuring a conjugated diene system with Z and E geometries, and an acetate functional group. (Z,E)-trideca-4,7-dien-1-yl acetate can be synthesized through a regioand stereo-controlled Beckmann fragmentation of trimethylsilylcycloalkanone oximes.

Uses

Used in Pest Control:
(Z,E)-trideca-4,7-dien-1-yl acetate is used as a pheromone in pest control for the potato tuber moth. (Z,E)-trideca-4,7-dien-1-yl acetate acts as a chemical attractant, luring the male moths towards the source of the pheromone, which can then be captured or monitored. This application helps in managing and controlling the population of the potato tuber moth, a significant agricultural pest that causes damage to potato crops.
Used in Chemical Synthesis:
(Z,E)-trideca-4,7-dien-1-yl acetate can also be used as a synthetic intermediate in the production of various chemicals and compounds. Its unique structure with the conjugated diene system and acetate functional group makes it a valuable building block for the synthesis of complex organic molecules, potentially leading to new materials and applications in various industries.
Used in Research and Development:
(Z,E)-trideca-4,7-dien-1-yl acetate (Z,E)-trideca-4,7-dien-1-yl acetate is utilized in research and development for studying the behavior and biology of the potato tuber moth and other related species. Understanding the chemical communication and mating patterns of these insects can provide valuable insights into their ecology and help develop more effective pest management strategies.

InChI:InChI=1/C15H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-17-15(2)16/h7-8,10-11H,3-6,9,12-14H2,1-2H3

Upstream product

• 57981-61-0 (4E,7Z)-4,7-Tridecadien-1-ol 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 68236-05-5 ethyl 4(E),7(Z)-tridecadienoate 
• 89682-47-3 (3Z)-3-nonenal diethyl acetal 
• 90290-02-1 3-nonynal diethyl acetal 
• 124381-46-0 (4E,7Z)-4,7-tridecadienal 
• 118495-88-8 (3Z)-1-vinyl-3-nonenyl vinyl ether 
• 31823-43-5 (Z)-3-nonenal 
• 628-71-7 1-Heptyne 
• 132124-56-2 (1E,4Z)-1-Bromo-deca-1,4-diene 
• 693-25-4 n-pentylmagnesium bromide 
• 89473-48-3 C₁₈H₃₃NO₂Si 
• 119220-73-4 (2R,3R)-2-((Z)-Oct-2-enyl)-3-trimethylsilanyl-cyclopentanone oxime 

Relevant articles and documents

A simple synthesis of 4E,7Z-tridecadien-1-yl acetate, a component of the sex pheromone of the potato moth Phtorimaea operculella (Lepidoptera: Gelehiidae)

A simple, five-step synthesis of the title compound was developed starting from commercially available 2,4-nonadienal. The overall yield of the pheromone is 29%, and the geometric purity of the Δ4 and Δ7 double bonds is ≥95%. The Z configuration of the Δ7 bond results from the 1,4-cis-hydrogenation of the intermediate 1,4,6-undecatrien-3-ol in the presence of an (arene)chromium tricarbonyl complex, while the E configuration of the Δ4 bond arises in the Claisen-Johnson rearrangement occuring in the reaction of 1,5Z-undecadien-3-ol with trimethyl orthoacetate.

Insect pheromones and their analogs LV. Synthesis of trideca-4E,7Z-dien-1-yl acetate - Component of the sex pheromone of Phthorimaea opercucella

Starting from propargyl alcohol and using the thermal Claisen rearrangement at the stage of constructing the (E)-double bond, we have synthesized trideca-4E, 7Z-dien-1-yl acetate - a component of the sex pheromone of the potato moth Phthorimaea opercucella (Zeller).

Stereoselective Synthesis of 1,4-Dienes. Application to the Preparation of Insect Pheromones (3Z,6Z)-Dodeca-3,6-dien-1-ol and (4E,7Z)-Trideca-4,7-dienyl Acetate

Stereoselective synthesis of Z,E- and Z,Z-1,4-dienes has been achieved by the cross-coupling of allylic substrates with vinyl organometallic reagents.Key to this strategy was the development of a method for regiospecific incorporation of a tri-n-butylstannyl group in the γ-position of the allylic cross-coupling partner.The steric bulk of this moiety ensures the stereochemical integrity of the allylic double bond throughout the coupling sequence and is easily replaced by hydrogen in the coupled product.This strategy has been applied to the synthesis of the termite trail marker pheromone 22 and the leafminer moth sex pheromone 28.