71317-73-2

Usage

Uses

Used in Flavor and Fragrance Industry:
11,13-Hexadecadienal,(11Z,13Z)is used as a flavoring agent for its characteristic aroma, adding a unique scent to various food products and beverages. Its natural occurrence in fruits and vegetables makes it a preferred choice for enhancing the taste and aroma of these products.
Used in Perfumery:
Due to its distinct and pleasant aroma, 11,13-Hexadecadienal,(11Z,13Z)is utilized as a fragrance ingredient in the production of perfumes and other scented products. Its ability to contribute to the overall scent profile makes it a valuable component in the creation of various perfumes.
Used in Pest Management:
11,13-Hexadecadienal,(11Z,13Z)has been identified as a potential attractant for certain pest insects. It is being studied for its potential use in pest management strategies, where it can be employed to attract and control pest populations, thereby reducing the need for chemical pesticides and promoting more sustainable agricultural practices.

InChI:InChI=1/C16H28O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h3-6,16H,2,7-15H2,1H3/b4-3-,6-5-

Upstream product

• 71673-23-9 (11Z,13Z)-1,1-diethoxy-11,13-hexadecadiene 
• 693-58-3 1-Bromononane 
• 2774-84-7 undec-10-yn-1-ol 
• 1214742-94-5 (Z)-1,1-diethoxyhexadec-13-en-11-yne 
• 1568-65-6 bis(cyclohexanyl)borane 
• 1214742-93-4 11-dodecynal diethyl acetal 
• 69064-46-6 dodec-2-yn-1-ol 
• 71720-83-7 (Z,Z)11,13-hexadecadien, 1-ol 
• 71673-31-9 1,1-diethoxy-11,13-hexadecadiyne 
• 85416-30-4 (Z)-12-Iodo-1-(2-tetrahydropyranyloxy)-11-dodecene 
• 85416-27-9 12-Iodo-1-(2-tetrahydropyranyloxy)-11-dodecyne 
• 51795-88-1 1-bromo-10-(tetrahydropyranyloxy)decane 
• 84433-06-7 (Z)-12-pentadecen-10-ynyl chloride 
• 84433-05-6 14-Chloro-1-tetradecen-4-yn-3-ol Acetate 

Downstream Products

• 73264-91-2 (11E,13E)-11,13-hexadecadienal 
• 71720-83-7 (Z,Z)11,13-hexadecadien, 1-ol 

Relevant academic research and scientific papers

Facile and efficient syntheses of (11Z,13Z)-hexadecadienal and its derivatives: Key sex pheromone and attractant components of notodontidae

Syntheses of (11Z,13Z)-hexadecadienal (1), (11Z,13Z)-hexadecadienol (2), (11Z,13Z)-hexadecadien-1-yl acetate (3), and (Z)-13-hexadecen-11-ynal (4) from commercially available starting material 10-bromo-1-decanol are reported. These (Z,Z)-dienes and conjugated en-yne moieties are common in sex pheromone and attractant components for many Notodontide insect pests. The synthetic scheme, using the C10 + C3 + C3 strategy, was mainly based on three key steps: Alkylation of lithium alkyne under a low temperature, cis-Wittig olefination of the aldehyde with propylidentriphenylphosphorane, and hydroboration-protonolysis of alkyne. This synthetic route provided (11Z,13Z)-hexadecadienal (1) in a 23.0% total yield via an eight-step sequence, alcohol (2) in a 21.9% total yield, acetate (3) in a 21.4% total yield, and (Z)-13-hexadecen-11-ynal (4) in a 34.7% total yield. This simple strategy provides a new way to achieve syntheses of the key sex pheromones of Notodontide insect pests.

Method for Producing Asymmetric Conjugated Diyne Compound and Method for Producing Z,Z-Conjugated Diene Compound Using the Same

Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC≡C—Z1—Y1 to a coupling reaction with an alkynyl halide (2) Y2—Z2—C≡C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y2—Z2—C≡C—C≡C—Z1—Y1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.

SYNTHETIC NAVEL ORANGEWORM PHEROMONE COMPOSITION AND METHODS RELATING TO PRODUCTION OF SAME

One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.

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.

Stereospecific Diene Synthesis using Acetylene Carbocupration; Preparation of Navel Orangeworm Pheromone and Leukotriene Analogues

Experimental conditions are described for the conversion of lithium dialkylcuprates into the corresponding doubly vinylogous 1Z,3Z-dienylcuprates using acetylene carbocupration.These dienylcuprates have been trapped with a range of electrophiles to form cconjugated Z,Z-dienes in a highly stereospecific manner.The application of this methodology to the synthesis of hexadeca-11Z,13Z-dienal, a principle component of navel orangeworm pheromone, and simple leukotriene B4 analogues is also reported.

Z,Z-DIENES VIA ACETYLENE CARBOCUPRATION: SYNTHESIS OF NAVEL ORANGEWARM PHEROMONE

A range of conjugated Z,Z-dienes have been prepared in a stereospecific manner via acetylene carbocupration: the value of this procedure has been illustrated by an extremely short synthesis of hexadeca-11Z, 13Z-dienal a principle component of Navel Orangewarm Pheromone.

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.