167820-65-7

Usage

Uses

Used in Flavor and Fragrance Industry:
(6Z)-nona-3,6-dien-1-ol is used as a key component in the creation of various fragrances and flavors due to its distinctive fruity and floral scent. This application takes advantage of the compound's natural aroma to enhance the sensory experience of consumer products.
Used as a Chemical Intermediate:
In the realm of organic chemistry, (6Z)-nona-3,6-dien-1-ol serves as a valuable intermediate in the synthesis of other complex organic compounds. Its unique structure facilitates chemical reactions that lead to the production of a wide range of products, showcasing its utility in the chemical industry.
Used in Pest Control:
(6Z)-nona-3,6-dien-1-ol is employed as a pheromone in the field of pest control, specifically as an attractant for the Mediterranean fruit fly. By mimicking the natural chemical signals used by these insects, (6Z)-nona-3,6-dien-1-ol can be used to lure and control their populations, providing an effective and environmentally friendly approach to pest management.

Upstream product

• 57386-91-1 nona-3,6-diyn-1-ol 
• 1638153-00-0 (3Z,6Z)-9,9-dimethoxy-nona-3,6-dien-1-yl 4-methylbenzenesulfonate 
• 696-86-6 cis,cis,cis-1,4,7-cyclononatriene 
• 1638152-99-4 (3Z,6Z)-9,9-dimethoxynona-3,6-dien-1-ol 
• 144647-88-1 [(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-hex-3-enyl]-triphenyl-phosphonium; bromide 
• 144460-30-0 ((Z)-6-Bromo-hex-3-enyloxy)-tert-butyl-diphenyl-silane 
• 122069-55-0 6-((tert-butyldiphenylsilyl)oxy)hex-3-yn-1-ol 
• 131138-00-6 (Z)-6-((tert-butyldiphenylsilyl)oxy)hex-3-en-1-ol 
• 16400-32-1 1-bromo-pent-2-yne 
• 81812-26-2 (Z,Z)-1,1-diethoxynona-3,6-diene 
• 6789-80-6 (3Z)-hexenal 
• 928-96-1 (Z)-3-Hexen-1-ol 
• 92666-05-2 toluene-4-sulfonic acid pent-2-ynyl ester 
• 6261-22-9 pent-2-yn-1-ol 

Downstream Products

• 90121-03-2 (3Z,6Z)-1-bromonona-3,6-diene 
• 81926-94-5 all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate 
• 90121-06-5 4-[((1E,3E,5Z,8Z,11Z)-3-Tetradeca-1,3,5,8,11-pentaenyl)-oxiranyl]-butyric acid methyl ester 
• 79695-14-0 LTE5 
• 79695-13-9 LTD5 
• 75207-09-9 LTC5 
• 169392-17-0 (4Z,7Z)-4,7-decadienoic acid 
• 118492-81-2 8(S)-hydroxy-(5Z,9E,11Z,14Z,17Z)-eicosapentaenoic acid 
• 26370-28-5 cis-3,cis-6-nonadienol 
• 163041-94-9 (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate 

Relevant academic research and scientific papers

Direct preparation of (Z,Z)-1,4-dienic units with a new C6 homologating agent: Synthesis of α-linolenic acid

Syntheses of two C6 homologating agents 2a and 2f are described. These agents allow direct access to the (Z,Z)-1,4-diene unit 3, a moiety present in a wide number of natural compounds. Compound 2a is prepared in 40% overall yield by selective epoxidation of methoxycyclohexa-1,4-diene followed by oxidative ring cleavage and transatalization. Compound 2f is obtained in 90% yield by a one-step oxidative dimerization of phosphonium salt 1. A short synthetic application of these two new C6 homologating agents to the synthesis of α-linolenic acid is described.

Pheromone synthesis. Part 257: Synthesis of methyl (2E,4Z,7Z)-2,4,7-decatrienoate and methyl (E)-2,4,5-tetradecatrienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)

Tandem Dess-Martin oxidation/Wittig reaction of (2Z,5Z)-2,5-octadien-1-ol yielded methyl (2E,4Z,7Z)-2,4,7-decatrienoate, a newly discovered pheromone component of the male dried bean beetle, while that of (±)-2,3-dodecadien-1-ol gave (±)-methyl (E)-2,4,5-tetradecatrienoate, the racemate of the known and major pheromone component. Methyl (2E,4E,7Z)-2,4,7-decatrienoate was also synthesized, which is the methyl ester of an acid metabolite of a green alga. Reduction of 2,5-octadiyn-1-ol with Zn-Cu/EtOH cleanly gave (2Z,5Z)-2,5-octadien-1-ol.

Total syntheses and in vivo quantitation of novel neurofuran and dihomo-isofuran derived from docosahexaenoic acid and adrenic acid

Neurofurans (NeuroFs) and dihomo-isofurans (dihomo-IsoFs) are produced in vivo by non-enzymatic free-radical pathways from docosahexaenoic and adrenic acids, respectively. As these metabolites are produced in minute amounts, their analyses in biological samples remain challenging. Syntheses of neurofuran and dihomo-isofurans described are based on a pivotal strategy, thanks to an enantiomerically enriched intermediate, which allowed, for the first time, access to both families: the alkenyl and enediol. Owing to this formation, quantitation of specific NeuroF and dihomo-IsoFs in biological samples was attainable.

A nine carbon homologating system for skip-conjugated polyenes

Ozonolysis of Z,Z,Z-cylonona-1,4,7-triene leads to a 1,9-difunctionalised Z,Z-3,6-nonadiene which is readily converted into a range of polyunsaturated pheromones and fatty acids.

Total synthesis and bioactivities of two proposed structures of maresin

Maresin is a potent anti-inflammatory lipid mediator derived from docosahexaenoic acid (DHA). A highly convergent total synthesis of two proposed structures of C7-epimeric maresins from the four known fragments was achieved in 17 steps. The three key coupling reactions were the BF3-mediated alkyne attack on the epoxide, chiral titanium complex-promoted enantioselective alkyne addition to the aldehyde, and a Julia-Kocienski olefination. The two synthesized diastereomers were found to be comparably active in blocking neutrophil infiltration in the acute peritonitis model. Copyright

Antioxidant behaviour of thia fatty acids

Eight thia fatty acids and other sulfides have been studied as inhibitors of autoxidation of arachidonic acid. The inhibitors extend the lag phase of the oxidation, to varying degrees. A carboxyl group in the vicinity of the sulfur reduces the antioxidant activity, while unsaturated sulfides are more effective than their saturated analogues. The results are consistent with the sulfides acting to reduce fatty acid hydroperoxides, which otherwise accumulate during the early stages of reaction and propagate the free-radical oxidation process.

Clean and Efficient Oxidation of Homoallylic and Homopropargylic Alcohols into β,γ-Unsaturated Aldehydes by The Dess-Martin Periodinane

We describe the first efficient oxidation of homoallylic and homopropargylic alcohols to the corresponding very sensitive and unstable β,γ-unsaturated aldehydes by using Dess-Martin periodinane with a new neutral and anhydrous extraction protocol.

First total synthesis of a barnacle hatching factor 8(R)-Hydroxy-eicosa-5(Z),9(E),11(Z),14(Z),17(Z)-pentaenoic acid

The first total synthesis of a barnacle hatching factor (BHF) establishes its constitution and absolute stereochemistry as 8(R)-Hydroxy-eicosa-5(Z),9(E),11(Z),14(Z),17(Z)-pentaenoic acid 1.

Total Stereospecific Synthesis of all cis-5,8,11,14,17-Eicosapentaenoic Acid (EPA)

Total stereospecific synthesis of EPA has been performed by a sequence of ozonolysis, selective reduction and Wittig reactions which affords the cis-skipped olefinic system.Versatile compound 4, readily prepared from dihydro anisole, allowed us to prepare the skipped dienic synthon 2 in high yield.Key Words: All cis-eicosapentanoic acid, EPA, cis-Wittig reaction, Ozonolysis.