89353-62-8

Usage

Uses

Used in the Food Industry:
(3Z,6Z,9Z)-3,6,9-Nonadecatriene is used as a natural flavor enhancer for its characteristic aroma derived from plant oils, particularly citrus fruits.
Used in the Fragrance Industry:
(3Z,6Z,9Z)-3,6,9-Nonadecatriene is used as a natural fragrance enhancer for its distinct aroma, adding a pleasant scent to various products.
Used in the Health and Wellness Industry:
(3Z,6Z,9Z)-3,6,9-Nonadecatriene is studied for its potential health benefits, including its anti-inflammatory and anti-cancer properties, making it a promising candidate for pharmaceutical applications.

InChI:InChI=1/C19H34/c1-3-5-7-9-11-13-15-17-19-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19H,3-4,6,8-10,12,14-16,18H2,1-2H3/b7-5-,13-11-,19-17-

Upstream product

• 111-83-1 1-bromo-octane 
• 125285-14-5 1-bromo-(2Z,5Z,8Z)-2,5,8-undecatriene 
• 17049-49-9 octylmagnesium bromide 
• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 
• 802294-64-0 propionic acid 
• 101339-95-1 (5Z,8Z)-5,8-undecadien-2-yn-1-ol 
• 88109-69-7 tetradeca-4-yn-1-ol 
• 115018-49-0 (4Z)-tetradec-4-en-1-al 
• 112-31-2 caprinaldehyde 
• 764-62-5 1-Jod-4-methoxybut-2-in 
• 3739-97-7 (trimethylsilyl)methylenetriphenylphosphorane 
• 84653-93-0 (3Z,6Z)-3,6-Hexadecadienyl(triphenyl)phosphonium iodide 
• 123-38-6 propionaldehyde 
• 92666-06-3 3,6,9-nonadecatriyne 

Relevant academic research and scientific papers

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.

Facile and efficient syntheses of (3Z,6Z,9Z)-3,6,9-nonadecatriene and homologues: Pheromone and attractant components of lepidoptera

Facile and efficient chemical syntheses of (3Z,6Z,9Z)-3,6,9-nonadecatriene and homologues from commercially available α-linolenic acid [(9Z,12Z,15Z)-9,12,15-octadecatrienoic acid] are reported. These straight-chain homoconjugated trienes are common sex pheromone and attractant components for many lepidopterous insect pests. The metal-catalyzed cross-coupling reactions between (9Z,12Z,15Z)-9,12,15-octadecatrienyl triflate and the appropriate Grignard reagents proceed very rapidly under notable mild conditions using Li2CuCl4 as catalyst in diethyl ether, and the resulting (3Z,6Z,9Z)-3,6,9-trienes with retention of geometrical configuration were in >92% isolated yield.

Use of the anti-oxidant butylated hydroxytoluene in situ for the synthesis of readily oxidized compounds: Application to the synthesis of the moth pheromone (Z,Z,Z)-3,6,9-nonadecatriene

The triene (Z,Z,Z)-3,6,9-nonadecatriene was synthesized in three steps from methyl linolenate. The key to the synthesis was the use of the anti-oxidant butylated hydroxytoluene in situ to provide protection of the unstable triene from autoxidation during reaction workup. This simple modification resulted in an increase in the yield from 20 to 85% over three steps. CSIRO 2007.

Synthesis of a pheromone of Boarmia selenaria via a Sila-Cope elimination. Stereochemical implications

The use of a Sila-Cope elimination afforded a Z,Z,Z trienamine derivative, direct synthetic precursor of (3Z,6Z,9Z)-3,6,9-nonadecatriene 1, one of the pheromone components of Boarmia selenaria. X-ray analysis of the tetrahydropyridinium salt 13 leading to

Identification and enantioselective synthesis of (Z,Z)-6,9-c/s-3S,4R-epoxynonadecadiene, the major sex pheromone component of Boarmia selenaria

(Z,Z)-6,9-cis-3S,4R-Epoxynonadecadiene has been identified as the major sex pheromone component of the Geometrid Boarmia selenaria. A short and efficient synthesis of the chiral methylene-interrupted diene-epoxide has been developed for both enantiomers.

Facile Synthesis of 1,4-Dienic Compounds from 4-Pentyn-1-ol: Synthesis of Pheromone Components of Boarmia Selenaria and B. Rhomboidaria

The bifunctionality of 4-pentyn-1-ol has been suitably exploited to prepare 1,4-dienic unit.This has been applied for the synthesis of two important sex pheromone components.

SYNTHETIC INVESTIGATIONS IN THE FIELD OF INSECT ATTRACTANTS (SEX ATTRACTANTS). SYNTHESIS OF METHYLENE-SEPARATED POLYENE HYDROCARBONS

3,6-Nonadecadiyne and 3,6-heneicosadiyne were obtained by the alkylation of 1-tetradecyne and 1-hexadecyne respectively with 1-bromo-1-pentyne. 2,6,9-Nonadecatriyne and 3,6,9-heneicosatriyne were obtained similarly by the alkylation of 1-undecyne and 1-tridecyne with 1-bromo-2,5-octadiyne.The hydrogenation of the polyacetylenic hydrocarbons in the presence of colloidal nickel catalyst gave the di- and triethylene hydrocarbons. cis,cis-3,6-Nonadecadiene, cis,cis-3,6-heneicosadiene, cis,cis,cis-3,6,9-nonadecatriene, and cis, cis, cis-3,6,9-heneicosatriene are components of the sex pheromones of the Arctiidae and Geometriidae families.

Pheromones, 57.- Synthesis of Lepidoptera Polyene Pheromones and of Structural Analogs.- Acetylenic Synthesis, Wittig Olefination, and Kolbe Electrolysis

By a combination of acetylenic syntheses with Wittig olefination as well as by mixed Kolbe electrolysis alkadienes, alkatrienes, and alkatetraenes (sex attractants of Lepidoptera and structural analogs)were synthesized.