73264-89-8

Usage

Uses

Used in Flavor and Fragrance Industry:
(Z,E)-11,13-Hexadecadienal is used as a flavoring agent for its characteristic aroma, which is responsible for the distinct smell of certain foods. It adds a unique and pleasant scent to various products in the industry.
Used in Antimicrobial Applications:
(Z,E)-11,13-Hexadecadienal is used as an antimicrobial agent due to its potential biological activities. It can help inhibit the growth of harmful microorganisms, making it a valuable component in the development of products that require preservation or have antimicrobial properties.
Used in Antioxidant Applications:
(Z,E)-11,13-Hexadecadienal is also used as an antioxidant agent. Its antioxidant properties can help protect products from oxidative damage, extending their shelf life and maintaining their quality over time. This makes it a useful component in the development of products that require protection against oxidation.

Upstream product

• 71720-83-7 (Z,Z)11,13-hexadecadien, 1-ol 
• 71673-23-9 (11Z,13Z)-1,1-diethoxy-11,13-hexadecadiene 
• 69064-46-6 dodec-2-yn-1-ol 
• 693-58-3 1-Bromononane 
• 152488-40-9 1-(2-tetrahydropyranyloxy)-2-dodecyne 
• 24724-18-3 10,11-Dibromo-1-undecanol 
• 1214742-94-5 (Z)-1,1-diethoxyhexadec-13-en-11-yne 
• 2774-84-7 undec-10-yn-1-ol 
• 83375-79-5 11-(Triphenyl-λ⁵-phosphanylidene)-undecan-1-ol 
• 941301-86-6 2-[((11Z,13E)-Hexadeca-11,13-dienyl)oxy]-tetrahydro-pyran 
• 78617-57-9 2-[((E)-Hexadec-13-en-11-ynyl)oxy]-tetrahydro-pyran 
• 71084-07-6 1-tetrahydropyranyloxy 11-dodecyne 
• 18202-10-3 11-dodecyn-1-ol 
• 111872-80-1 (11Z,13E)-11,13-hexadecadien-1-ol 

Relevant academic research and scientific papers

New synthesis of (11Z,13Z)-11,13-Hexadecadienal, the female sex pheromone of the navel orangeworm

(11Z,13Z)-11,13-Hexadecadienal, the female sex pheromone of the navel orangeworm (Amyelois transitella), was synthesized from commercially available 10-bromo-1-decanol in a 27% overall yield (8 steps). The synthesis was achieved by using 10-iododecanal, trimethylsilylacetylene and (Z)-1-bromo-12-butene as the key building blocks, employing Sonogashira-Hagihara coupling and Brown's hydroboration-protonolysis as the key reactions. The terminal formyl group was installed in the earlier stage of the synthesis rather than in the final step. This procedure enabled the multi-gram-scale preparation of this economically important pheromone.

Synthetic pheromone compositions

The present invention provides compounds useful for preparing synthetic pheromone compositions that can be used as attractants or inhibitors of insect species. The compositions are useful in the control of navel orangeworm or meal moth insect pests.

A CONVENIENT SYNTHESIS OF (11E,13E)-11,13-HEXADECADIENAL AND (11Z,13E)-HEXADECADIENAL

A simple method for synthesizing (11E,13E)-11,13-hexadecadienal 7, a component of the female sex pheromone of cabbage webworm, and its geometrical isomer (11Z,13E)-11,13-hexadecadienal 8 is described.

Synthesis of (Z,Z)-11,13-Hexadecadienal, a Principal Component of Navel Orangeworm (Pamyelois transitella) Pheromone

This report outlines a commercial synthetic process for (Z,Z)-11,13-hexadecadienal (navel orangeworm pheromone).The synthetic scheme which is employed introduces the stereochemically labile conjugated diene moiety at a late stage in the synthesis, thereby avoiding complications during the purification of intermediates.In addition, the aldehyde function is generated through a Grignard reaction sequence, obviating the generally accepted techniques which are usually unsuitable for commercial preparations.We have also observed the first reported selective inclusion by urea of a conjugated (Z,Z)-diene as a means of mild purification of labile dienic pheromone intermediates.