7328-34-9

Basic information

• Product Name: ethyl (2E,4E)-2,4-decadienoate
• Synonyms: 2,4-Decadienoic acid, ethyl ester, (2E,4E)-; E,E-Ethyl 2,4-decadienoate; 2,4-Decadienoic acid, ethyl ester, (E,E)-; Ethyl (2E,4E)-2,4-decadienoate; ethyl (2E,4E)-deca-2,4-dienoate
• CAS NO: 7328-34-9
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.286
• EINECS: 230-816-4
• Mol File: 7328-34-9.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 264.7°C at 760 mmHg
• Flash Point: 118.3°C
• Density: 0.903g/cm³
• Vapor Pressure: 0.00954mmHg at 25°C
• Refractive Index: 1.46
• CAS DataBase Reference: ethyl (2E,4E)-2,4-decadienoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2E,4E)-2,4-decadienoate(7328-34-9)
• EPA Substance Registry System: ethyl (2E,4E)-2,4-decadienoate(7328-34-9)

Safety Data

• Hazardous Substances Data: 7328-34-9(Hazardous Substances Data)

Usage

General Description

Ethyl (2E,4E)-2,4-decadienoate is a chemical compound that belongs to the class of esters, consisting of ethyl alcohol and 2,4-decadienoic acid. It is commonly used as a flavoring agent in food and beverages due to its fruity and sweet aroma, reminiscent of fruits such as apple and pear. Ethyl (2E,4E)-2,4-decadienoate is also used in the production of perfumes and fragrances, as well as in the formulation of cosmetic and personal care products. Additionally, it has been studied for its potential insecticidal properties and is used in the formulation of insect repellents. Overall, ethyl (2E,4E)-2,4-decadienoate is a versatile chemical with a wide range of applications in various industries.

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Downstream Products

• 30361-33-2 (2E,4E)-deca-2,4-dienoic acid 
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• 544-48-9 (2E,4E)-Deca-2,4-dienoic acid 

Relevant articles and documents

ENE REACTION OF α-THIOCARBOCATION: SIMPLE SYNTHESIS OF E,E-2,4-ALKADIENOIC ESTERS FROM 1-ALKENES

Pummerer reaction intermediate 2 of α-methylsulfinylacetate(1) has been found to react with 1-alkenes to afford ene adducts 3.E,E-2,4-decadienoic ester (5) was synthesized from the adduct 3 (n=5).

Reconstitution of a Type II Polyketide Synthase that Catalyzes Polyene Formation

While type II polyketide synthases (PKSs) are known for producing aromatic compounds, a phylogenetically new subfamily of type II PKSs have been recently proposed to synthesize polyene structures. Here we report in vitro analysis of such a type II PKS, IgaPKS for ishigamide biosynthesis. The ketoreductase (Iga13) and dehydratase (Iga16) were shown to catalyze the reduction of a β-keto group and dehydration of a β-hydroxy group, respectively, to form a trans double bond. Incubation of the acyl carrier protein (Iga10), the ketosynthase/chain length factor complex (Iga11–Iga12), Iga13 and Iga16 with malonyl and hexanoyl-CoAs and NADPH followed by KOH hydrolysis resulted in the formation of four unsaturated carboxylic acids (C8, C10, C12, and C14), indicating that IgaPKS catalyzes tetraene formation by repeating the cycle of condensation, keto-reduction and dehydration with strict stereo-specificity. We propose “highly reducing type II PKS subfamily” for the polyene-producing type II PKSs.

Concise preparation of the (3E,5Z)-alkadienyl system. New approach to the synthesis of principal insect sex pheromone constituents

A new rapid and low-cost preparation of the (3E,5Z)-3,5-alkadienyl system, encountered in several insect pheromone constituents, was developed. Knoevenagel condensation of (E)-2-alkenals with ethyl hydrogen malonate in dimethyl sulfoxide, in the presence of a catalytic amount of piperidinium acetate, led to a mixture of geometrical isomers of ethyl 3,5-alkadienoates and ethyl 2,4-alkadienoates, from which the (3E,5Z)-3,5-alkadienoate was conveniently separated, by the use of urea inclusion complex formation. The importance of this procedure has been illustrated by the preparation of the (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid) 1, the (3E,5Z)-3,5- dodecadienyl acetate 2, and the (3E,5Z)-3,5-tetradecadienyl acetate 3. These compounds are the main components of insect sex pheromones and constitute synthetic targets of considerable interest for the semiochemical community.