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Usage

Uses

Used in Pheromone Applications:
2,4,6-Nonatrienal, (2E,4E,6E)is used as a pheromone component for attracting female flea beetles. It plays a crucial role in the mating and reproduction process of these insects.
Used in Flavor and Fragrance Industry:
2,4,6-Nonatrienal, (2E,4E,6E)is used as a flavoring agent and fragrance ingredient due to its unique aroma and taste. It contributes to the overall sensory experience of various food and cosmetic products.
Used in Medicinal Applications:
2,4,6-Nonatrienal, (2E,4E,6E)is used in the development of pharmaceuticals and herbal remedies, particularly in the context of licorice root's medicinal properties. Its presence in licorice root may contribute to the herb's therapeutic effects, such as anti-inflammatory, antiviral, and immune-modulating activities.

Upstream product

• 1576-86-9 cis-2-penten-1-one 
• 72967-11-4 (3-methoxycarbonyl-2-propenyl)triphenylphosphonium bromide 
• 1576-87-0 trans-2-pentenal 
• 1576-95-0 cis-2-penten-1-ol 
• 4313-03-5 (2E,4E)-hepta-2,4-dienal 
• 56424-97-6 (2E,4E)-methyl hepta-2,4-dienoate 
• 922528-07-2 ethyl (E,E,E)-2,4,6-nonatrienoate 
• 18937-78-5 methyl 2-heptynoate 
• 693-02-7 hex-1-yne 
• 2798-73-4 1-methoxy-buten-3-yne 

Downstream Products

• 108670-78-6 3'-(1E/Z,3E,5E,7E-Decatetraenyloxy)-1,2-propanediol 
• 127072-58-6 3'-(1E/Z,3E,5E,7E,9E,11E-Tetradecahexaenyloxy)-1,2-propanediol 

Relevant academic research and scientific papers

Identification and formation of volatile components responsible for the characteristic aroma of mat rush (Igusa)

An aroma concentrate of the mat rush (igusa) was prepared by combining solvent extraction with the solvent-assisted flavor evaporation (SAFE) technique. An aroma extract dilution analysis (AEDA) applied to the volatile fraction revealed 51 odor-active peaks with FD factors between 43 and 47. Among the perceived odorants, twelve peaks with the higher FD factors (≥46) were proved to be the most important components of the characteristic aroma in mat rush. Eleven odorants were identified or tentatively identified from the twelve peaks as methional, (E, Z)-2, 6-nonadienal, (E)-2-nonenal, (E,E)-2, 4-nonadienal, (E,E,Z)-2,4,6-nonatrienal, trans-4,5-epoxy-(E)-2-decenal, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, isovaleric acid, methyl anthranirate, and vanillin. The FD factors of the odor-active peaks in dried mat rush were observed to be much higher than those in raw mat rush. This finding suggests that the drying process during manufacturing of the mat rush Is one of the most important factors for the formation of the characteristic mat rush aroma.

Characterization of (E,E,Z)-2,4,6-nonatrienal as a character impact aroma compound of oat flakes

To identify the compounds evoking the characteristic cereal-like, sweet aroma of oat flakes, an aroma extract dilution analysis (AEDA) was applied to a distillate prepared by solvent extraction/vacuum distillation from commercial oat flakes. Among the nine aroma-active compounds detected by gas chromatography-olfactometry and AEDA in the flavor dilution (FD) factor range of 4-1024, eight odorants, for example, (E)-β-damascenone, (Z)-3-hexenal, and butanoic acid, showed only low FD factors. However, one odorant eliciting the typical cereal, sweet aroma of the flakes was detected with the highest FD factor of 1024. By mass spectrometry and nuclear magnetic resonance measurements followed by a synthesis, (E,E,Z)-2,4,6-nonatrienal, exhibiting an intense oat flake-like odor at the extremely low odor threshold of 0.0002 ng/L in air, was identified as the key odorant of the flakes. By means of a newly developed stable isotope dilution analysis using synthesized, carbon-13-labeled nonatrienal as the internal standard, a concentration of 13 μg of (E,E,Z)-2,4,6-nonatrienal per kilogram of the flakes was measured. Model studies suggested linolenic acid as the precursor of nonatrienal in oats.

Triphenylphosphine Oxide-Catalyzed Selective α,β-Reduction of Conjugated Polyunsaturated Ketones

The scope of the triphenylphosphine oxide-catalyzed reduction of conjugated polyunsaturated ketones using trichlorosilane as the reducing reagent has been examined. In all cases studied, the α,β-C=C double bond was selectively reduced to a C-C single bond while all other reducible functional groups remained unchanged. This reaction was applied to a large variety of conjugated dienones, a trienone, and a tetraenone. Additionally, a tandem one-pot Wittig/conjugate-reduction reaction sequence was developed to produce γ,δ-unsaturated ketones directly from simple building blocks. In these reactions the byproduct of the Wittig reaction served as the catalyst for the reduction reaction. This strategy was then used in the synthesis of naturally occurring moth pheromones to demonstrate its utility in the context of natural-product synthesis.

Acid-catalyzed solvolysis of polyenol ethers. II. Effect of the degree of unsaturation

The acid-catalyzed solvolysis of polyenol ethers of glycerol gradually changes with increasing unsaturation from the regular pattern into an anomalous one in which hydroxy- and methoxy-substituted aldehydes are formed.

A CONVENIENT SYNTHESIS OF FECAPENTAENE-12 BY THE HORNER-WITTIG REACTION

A synthesis of racemic fecapentaene-12 and other glyceryl enol ethers has been developed based on the Horner-Wittig reaction.Coupling of the anion of the glyceryl substituted phosphine oxide 7 with unsaturated aldehydes 9a-c provided, after treatment with base, the silyl protected glyceryl enol ethers 11a-c.The silyl groups were easily removed and mixtures of E and Z isomers of glyceryl enol ethers 12a-c were obtained.The isomers could be separated upon washing with ether/hexane.