2277-15-8

Usage

Uses

Used in Flavor and Fragrance Industry:
(Z)-4-Nonenal is used as an additive in the flavor and fragrance industry to provide the odor of old age or decay. This application takes advantage of the compound's strong, unpleasant smell, which can be used to create realistic and authentic scents in various products.
Used in Research and Diagnostics:
(Z)-4-Nonenal is used as a biomarker in research and diagnostics, particularly in the study of certain health conditions. Its presence in the exhaled breath of individuals with specific health issues makes it a valuable tool for identifying and monitoring these conditions.
Used in Aging Studies:
(Z)-4-Nonenal is used as a subject of study in aging research, as it has been suggested to play a role in the aging process. Understanding the compound's involvement in aging may lead to insights into age-related health issues and potential interventions or treatments.
Used in Food Industry:
Although not explicitly mentioned in the provided materials, (Z)-4-Nonenal's presence in certain foods, such as vegetable oils and meats, suggests that it may have applications in the food industry. It could be used to study the effects of oxidation and degradation on food quality, shelf life, and flavor, potentially leading to improved food preservation techniques and product development.

Upstream product

• 59499-28-4 (Z)-4-nonen-1-ol 
• 39924-28-2 (Z)-4-Nonensaeure-ethylester 
• 54068-77-8 (4Z)-1,4-nonadiene 
• 110-62-3 pentanal 
• 4938-52-7 1-hepten-3-ol 
• 82861-01-6 1,1-dimethoxy-8-tosyloxy-(4Z)-octene 
• 16538-47-9 (Z)-1-iodohex-1-ene 
• 107-18-6 allyl alcohol 
• 116206-56-5 1,1-dimethoxy-(4Z)-nonene 
• 80816-20-2 l-butyl-2-propenyl-vinyl ether 

Downstream Products

• 209734-30-5 (Z)-2-benzyl-3-oct-3'-enyloxaziridine 
• 59499-28-4 (Z)-4-nonen-1-ol 
• 16725-53-4 (Z)-9-tetradecen-1-yl acetate 
• 35153-15-2 (Z)-9-tetradecen-1-ol 
• 59499-29-5 (Z)-4-nonenyl bromide 

Relevant academic research and scientific papers

Metalloporphyrin Cr(TPP)Cl-catalyzed Claisen rearrangement of simple aliphatic allyl vinyl ethers and its unique stereoselectivity

The catalytic Z-selective Claisen rearrangement of simple aliphatic allyl vinyl ethers can be achieved using a chromium(III) porphyrin complex, Cr(TPP)Cl, as a catalyst: Cr(TPP)Cl significantly enhances reversal of E-Z selectivity in the thermal Claisen r

PALLADIUM-CATALYSED REACTION OF VINYLIC HALIDES WITH PRIMARY ALLYLIC ALCOHOLS: REGIO AND STEREOCONTROLLED SYNTHESIS OF 4-ENALS.

Stereodefined γ,δ-unsaturated aldehydes can be prepared with high regio and stereocontrol by palladium-catalysed coupling of vinylic halides with primary allylic alcohols, in the presence of silver carbonate and tetra-n-butylammonium hydrogen sulphate.

OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XLII. SYNTHESIS OF (9Z)-TETRADECENYL ACETATE AND (9Z)-HEXADECENAL FROM (Z,Z)-1,5-CYCLOOCTADIENE

A stereocontrolled synthesis of (9Z)-tetradecenyl acetate and (9Z)-hexadecenal, which are components of the sex pheromones of the pine (Panolis flammea) and cotton (Heliothis armigera) moths respectively, was realized on the basis of the partial ozonolysis of (Z,Z)-1,5-cyclooctadiene.

Ozonolysis of alkenes and study of the reactions of polyfunctional compounds. XXXIII. Synthesis of (Z)-7-oxo-10-hexadecen-1-ol and its noranalog

A pathway has been developed for the synthesis of (Z)-7-oxo-10-hexadecen-1-ol, which is a cancer inhibitor, and its noranalog, (Z)-7-oxo-10-pentadecen-1-ol, based on the partial ozonolysis of (Z,Z)-1,5-cyclooctadiene leading to 1,1-dimethoxy-8-tosyloxy-4Z-octene.Subsequent simple transformations of the hydrocarbon skeleton give the desired compounds in five steps.

ALIPHATIC CLAISEN REARRANGEMENT PROMOTED BY ORGANOALUMINIUM REAGENTS.

Organoaluminium compounds, R//3Al, promote the Claisen rearrangement of allyl vinyl ether derivatives at room temperature under transfer of R or H as a nucleophile to the aldehydic carbon. Treatment of 1-butyl-2-propenyl vinyl ether with a hexane solution of Me//3Al (1. 0 M, 2. 2 equiv) in CH//2ClCH//2Cl at 25 degree C afforded 5-decen-2-ol (91% yield, E/Z equals 47/53), which was produced by the left bracket 3,3 right bracket sigmatropic rearrangement and successive methylation. The rearrangements with alkynylation, alkenylation, and hydrogenation are also achieved. The regular Claisen rearrangement products, of gamma , delta -unsaturated aldehydes (ketones), are obtained at 25 degree C in good to excellent yields with Et//2AlSPh (2. 5 equiv) or the combination of Et//2AlCl (2. 0 euiv) and PPh//3 (2. 2 equiv).