23400-52-4

Basic information

• Product Name: (3E,5Z)-3,5-Tetradecadienoic acid
• Synonyms: (3E,5Z)-3,5-Tetradecadienoic acid;Megatomoic acid;(Z,Z)-3,5-Tetradecadienoic acid;(3E,5Z)-tetradecadienoic acid
• CAS NO: 23400-52-4
• Molecular Formula: C14H24O2
• Molecular Weight: 224.3392
• Mol File: 23400-52-4.mol

Chemical Properties

• Boiling Point: 354.7°Cat760mmHg
• Flash Point: 251.7°C
• Appearance: /
• Density: 0.929g/cm³
• Vapor Pressure: 5.48E-06mmHg at 25°C
• Refractive Index: 1.479
• CAS DataBase Reference: (3E,5Z)-3,5-Tetradecadienoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3E,5Z)-3,5-Tetradecadienoic acid(23400-52-4)
• EPA Substance Registry System: (3E,5Z)-3,5-Tetradecadienoic acid(23400-52-4)

Safety Data

• Hazardous Substances Data: 23400-52-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3E,5Z)-3,5-Tetradecadienoic acid is used as an active pharmaceutical ingredient for its potential therapeutic effects. The specific configuration of the double bonds in this molecule allows it to interact with biological systems in ways that could be beneficial for treating certain health conditions.
Used in Cosmetics Industry:
In the cosmetics industry, (3E,5Z)-3,5-Tetradecadienoic acid is used as an ingredient in skincare and hair care products due to its moisturizing and emollient properties. The long-chain structure and double bonds provide a smooth texture and enhance the product's ability to penetrate and nourish the skin or hair.
Used in Nutritional Supplements:
(3E,5Z)-3,5-Tetradecadienoic acid is used as a component in nutritional supplements, particularly those targeting heart health and brain function. The polyunsaturated nature of this fatty acid contributes to the overall balance of essential fatty acids in the diet, which is crucial for maintaining optimal health.
Used in Research and Development:
(3E,5Z)-3,5-Tetradecadienoic acid is also utilized in research and development for its potential applications in various fields. Scientists and researchers explore its properties and interactions with biological systems to discover new uses and develop innovative products.

InChI:InChI=1/C14H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-12H,2-8,13H2,1H3,(H,15,16)/b10-9+,12-11-

Upstream product

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• 115478-89-2 (3E,5Z)-3,5-tetradecadienol 
• 764-93-2 1-decyne 
• 98506-24-2 ethyl (2E,4E)-tetradeca-2,4-dienoate 
• 20407-84-5 2-dodecenal 
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• 95646-13-2 (E)-tetradeca-3-en-5-yn-1-ol 

Relevant articles and documents

A Stereoselective Synthesis of (3E,5Z)-3,5-Tetradecadienoic Acid (Megatomoic Acid), the Sex Attractant of the Black Carpet Beetle

The total synthesis of (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid) is accomplished with 74percent stereoselectivity through the use of stereoselective rearrangement of ethyl 3,4-tridecadienoate to ethyl (2E,4Z)-2,4-tridecadienoate with alumina and the extension of the carbon chain with methyl methylthiomethyl sulfone.

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.

Short-route synthesis of (3E,5Z)-tetradecadienoic acid (megatomic acid), the sex attractant of the black carpet beetle

A new and expeditious route to (3E,5Z)-3,5-tetradecadienoic acid (megatomic acid), the sex attractant of the black carpet beetle Attagenus megatoma (Fabricius), is reported which proceeds with 97% stereoselectivity; Cadiot-Chodkiewicz cross-coupling of 1-decyne and 4-bromo-3-butyn-1-ol in the presence of CuCl, followed by stereoselective reductions and Jones oxidation, gives the target molecule, with the synthetic pheromone showing a positive electrophysiological response.

Selective Proton Transfer of Unsaturated Esters. Syntheses of A Trail-Following Pheromone for Subterranean Termites and Megatomoic Acid

Deconjugative protonation of dienolates from (E)-2-alkenoate using potassium disilazide as the base gives (Z)-3-alkenoate predominantly.A trail-following pheromone for subterranean termites is synthesized stereoselectively with this method.Deconjugative protonation of trienolates from (E,E)-2,4-tetradecadienoates gives (E,Z)-3,5-tetradecanoates which is hydrolyzed to give Megatomoic acid, a sex pheromone for a black carpet beetle Attagenus megatoma.

Isomerization of acetylenic acids with sodium salt of 1,2-diaminoethane: a one step synthesis of megatomic acid

A number of isomeric tetradecynoic acids were isomerized with the sodium salt of 1,2-diaminoethane.Isomers having the triple bond near the carboxyl group rearranged to E,Z-3,5- and E,E-3,5-tetradecadienoic acids (1 and 2), the former compound being the sex pheromone of the black carpet beetle.Isomers having the triple bond closer to the terminus of the chain afforded some 13-tetradecynoic acid along with 1 and 2.Delocalized anions 12 and 13 are thought to contribute to the formation of 1 and 2.