57006-69-6

Basic information

• Product Name: Acetic acid (2E,4E)-2,4-hexadienyl ester
• Synonyms: Acetic acid (2E,4E)-2,4-hexadienyl ester;(E,E)-sorbyl acetate
• CAS NO: 57006-69-6
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.18
• Mol File: 57006-69-6.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Acetic acid (2E,4E)-2,4-hexadienyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (2E,4E)-2,4-hexadienyl ester(57006-69-6)
• EPA Substance Registry System: Acetic acid (2E,4E)-2,4-hexadienyl ester(57006-69-6)

Safety Data

• Hazardous Substances Data: 57006-69-6(Hazardous Substances Data)

Usage

Description

Acetic acid (2E,4E)-2,4-hexadienyl ester, also known as (2E,4E)-hexa-2,4-dien-ol acetate, is a naturally occurring organic compound that can be isolated from the scent glands of various Heteroptera and from the defense secretions of Thaumastella spp. It is characterized by its unique (2E,4E)-hexa-2,4-dienyl ester functional group, which gives it distinct chemical properties and potential applications in various fields.

Uses

Used in Chemical Synthesis:
Acetic acid (2E,4E)-2,4-hexadienyl ester is used as a key intermediate in regioselective cycloadditions with a variety of dienophiles. Its unique (2E,4E)-hexa-2,4-dienyl ester functional group allows for selective reactions, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pheromone Production:
Acetic acid (2E,4E)-2,4-hexadienyl ester is used as a sex pheromone in various insect species, particularly in the Heteroptera order. Its ability to attract and stimulate mating behavior in these insects makes it an important component in pest control and monitoring programs.
Used in Defense Secretions:
In addition to its role as a sex pheromone, Acetic acid (2E,4E)-2,4-hexadienyl ester is also found in the defense secretions of Thaumastella spp. Its presence in these secretions suggests that it may have defensive properties, such as repelling predators or deterring attacks from other organisms.
Overall, Acetic acid (2E,4E)-2,4-hexadienyl ester is a versatile compound with a range of applications in chemical synthesis, pheromone production, and defense secretions. Its unique chemical structure and natural occurrence make it an interesting target for further research and development in these fields.

Upstream product

• 110-44-1 sorbic Acid 
• 108-24-7 acetic anhydride 
• 689-89-4 (2E,4E)-methylhexa-2,4-dienoate 
• 17102-64-6 Sorbyl alcohol 
• 114628-86-3 1,3-diacetoxy-4-hexene 
• 114988-53-3 1-acetoxy-3-acetoxymethoxy-4-hexene, E isomer 
• 127-09-3 sodium acetate 
• 80639-18-5 (E)-1,4-hexadien-3-yl acetate 
• 91001-07-9 (E)-hexa-1,4-dien-3-ol 
• 114988-54-4 4-propenyl-1,3-dioxane, E-isomer 
• 108965-77-1 (E)-(2S,3S)-2-Hydroxy-3-trimethylsilanyl-hex-4-enoic acid methyl ester 

Downstream Products

• 33956-49-9 (8E,10E)-dodeca-8,10-dienol 
• 70729-06-5 [Bis-(4-methoxy-phenyl)-methyl]-((2E,4E)-hexa-2,4-dienyl)-amine 
• 70729-07-6 [Bis-(4-methoxy-phenyl)-methyl]-bis-((2E,4E)-hexa-2,4-dienyl)-amine 
• 533-18-6 2-methylphenyl acetate 
• 115270-12-7 1-<(tert-butoxycarbonyl)amino>-2(E),4(E)-hexadiene 
• 112-30-1 1-Decanol 
• 7735-43-5 1,20-eicosanediol 
• 68252-11-9 trans,trans-hexadeca-12,14-dien-1-ol 
• 111-28-4 hexa-2,4-dienyl alcohol 
• 37935-49-2 (8E,10E)-8,10-Dodecadienyl-(tetrahydro-2-pyranyl)ether 
• 105273-54-9 1-((E)-1-Vinyl-but-2-enyl)-cyclohexanol 
• 105273-55-0 ((2E,4E)-1-Hexa-2,4-dienyl)-cyclohexanol 
• 105273-53-8 1-((E)-1-Methyl-penta-2,4-dienyl)-cyclohexanol 

Relevant articles and documents

Synthesis method of laspeyresia pomonella sex pheromone

The invention relates to a synthesis method of laspeyresi pomonella sex pheromone. The method comprises the steps as follows: (1) methanol is added to methyl sorbate as a raw material, and an intermediate A sorbic alcohol is obtained through 5% palladium-carbon catalytic hydrogenation reduction; (2) the intermediate A sorbitol obtained in (1) and acetic anhydride are subjected to a reaction in ethyl acetate, triethylamine and water to obtain an intermediate B sorbic acetate; (3) 6-chlorohexanol is subjected to a reaction with trimethylchlorosilane in toluene in the presence of ethyl acetate and triethylamine, after the reaction, water is added, stirring and layering are performed, and an intermediate C6-chlorohexanol trimethylsilyl ester is obtained; (4) the intermediate B sorbic acetate and the intermediate C6-chlorohexanol trimethylsilyl ester are subjected to a reaction with sodium sand in a toluene solution, then, water and sulfuric acid are dropwise added, layering and rectification are performed, and a target product E8,E10-dodecadiene-1-ol is obtained. The synthesis method has the advantages as follows: the laspeyresi pomonella sex pheromone is synthesized from available rawmaterials, the reaction route is short, and the selectivity and product yield can be increased.

An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Readily Available Starting Materials

Cyclohexanone-derived Knoevenagel adducts (cyclohexylidenemalononitriles) and two different propargyl electrophiles serve as carbon sources for assembling diverse 6/7/5 tricycloalkanes, a common terpenoid framework. The sequence involves three unique reac

Chiral gold complex-catalyzed hetero-diels-alder reaction of diazenes: Highly enantioselective and general for dienes

A chiral gold(I) complex-catalyzed highly regio- and enantioselective azo hetero-Diels-Alder reaction has been developed. The chiral gold(I) complex acting as a Lewis acid exhibits high efficiency in the activation of urea-based diazene dienophiles. Moreover, this chiral gold catalyst also rendered a cascade intramolecular enyne cycloisomerization/asymmetric azo-HDA reaction.