4124-88-3

Usage

Uses

Used in the Food Industry:
3-Nonenoic acid is used as a flavoring agent for its distinctive fruity and slightly sweet aroma, enhancing the taste and aroma of various food products.
Used in the Fragrance Industry:
3-Nonenoic acid is utilized as a key ingredient in the production of fragrances, capitalizing on its pleasant and appealing scent to create a wide range of olfactory experiences.
Used in the Pharmaceutical Industry:
3-Nonenoic acid serves as a precursor in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and treatments.
Used in Chemical Synthesis:
As a versatile chemical intermediate, 3-Nonenoic acid is employed in the synthesis of other organic compounds, expanding its applications across different chemical processes.
Used in the Cosmetic Industry:
Leveraging its antimicrobial properties, 3-Nonenoic acid is studied for its potential use as a preservative in cosmetics, helping to maintain product integrity and prevent microbial contamination.
Used as a Preservative in the Food Industry:
3-Nonenoic acid's antimicrobial characteristics are being explored for use as a natural preservative in the food industry, offering an alternative to synthetic preservatives and extending the shelf life of food products.

InChI:InChI=1/C9H16O2/c1-2-3-4-5-6-7-8-9(10)11/h6-7H,2-5,8H2,1H3,(H,10,11)/b7-6+

Upstream product

• 111-71-7 heptanal 
• 141-82-2 malonic acid 
• 111-66-0 oct-1-ene 
• 693-03-8 n-butyl magnesium bromide 
• 7379-74-0 β-vinyl-β-propiolactone 
• 24406-16-4 lithium di-n-butylcuprate 
• 68079-35-6 CH₃CH₂CH₂CH₂Cu*BF₃ 
• 70180-12-0 butylcopper tributylphosphine 
• 201230-82-2 carbon monoxide 
• 147583-38-8 1-vinyl hexyl diethyl phosphate 
• 36781-67-6 methyl (trans-3-nonenoate) 
• 3913-80-2 (E)-2-octen-1-yl acetate 
• 124-38-9 carbon dioxide 
• 18409-17-1 (E)-oct-2-en-1-ol 

Downstream Products

• 10339-61-4 3-nonene-1-ol 
• 36781-67-6 methyl non-3-enoate 

Relevant academic research and scientific papers

Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy

A direct and general method for the synthesis of naturally occurring 2,3,4,5,6-pentasubstituted tetrahydropyrans has been developed, employing β,γ-unsaturated N-acyl oxazolidin-2-ones as key starting materials. The combination of the Evans aldol addition and the Prins cyclization allowed the diastereoselective and efficient generation of the desired oxacycles in two fashions: a one-pot Evans aldol-Prins protocol, in which five new σ bonds and five contiguous stereocenters were straightforwardly generated, and a two-step version, which additionally permitted the isolation of β,γ-unsaturated alcohol precursors bearing an N-acyl oxazolidin-2-one in the α position. From these alcohols were also obtained halogenated pentasubstituted tetrahydropyrans as well as 2,3,4,5-tetrasubstituted tetrahydrofurans, shedding light on the mechanism of the process. Computational studies were consistent with the experimental findings, and this innovative Evans aldol-Prins strategy was performed for the preparation of a battery of more than 30 densely substituted tetrahydropyrans, unprecedentedly fused to a 1,3-oxazinane-2,4-dione ring, both in a racemic fashion and in an enantiomeric fashion. These novel molecules were successfully submitted to several transformations to permit simple access to a variety of differently functionalized tetrahydropyrans. Most of these unique molecules were evaluated for their antimicrobial activity against Gram-positive and Gram-negative bacteria and the yeast Candida albicans, and some structure-activity relationships were established.

Synthetic method γ - nonene lactone

The invention relates to a synthesis method of γ - nonenolide, belongs to the technical field of perfume synthesis, first steps of adding malonic acid into a four-port flask containing a condensing tube and a water separator, adding piperidine, and then adding heptanal to the 95 - 105 °C condition to raise the temperature and react to obtain the intermediate 1. The second Acetic acid and hydrogen peroxide are mixed, the intermediate 1 is added dropwise, the control temperature is 40 °C, and the intermediate 2 is obtained. The third Intermediate 2, dichloromethane and triethylamine were mixed and acetyl chloride was added dropwise, and after the dropwise addition, γ - nonene lactone was obtained. No solvent is used in first steps of the invention, so that the reaction cost is reduced. The intermediate 1 is closed under the action of acetic acid and hydrogen peroxide, adopts hydrogen peroxide as an oxidant, and has the advantage of environmental friendliness. By replacing methane sulfonyl chloride with acetyl chloride, the use of methane sulfonyl chloride is reduced under the condition of ensuring the yield, the whole reaction process is simple, the route is short, and the raw materials are easily available.

A practical copper-catalyzed approach to β-lactams: via radical carboamination of alkenyl carbonyl compounds

Functionalized β-lactams are highly important motifs in synthetic chemistry. We report an efficient and novel approach to the synthesis of β-lactams via a copper(i)-catalyzed cascade process involving C(benzyl)-H radical abstraction, intermolecular alkene addition, and intramolecular amination reaction. Variously substituted alkenes were synthesized from vinylacetic acid, leading to the corresponding β-lactams in moderate to good yields. Preliminary studies indicate that the reaction undergoes a free radical mechanism via a Cu(i)/Cu(ii)/Cu(iii) catalytic cycle.

Catalytic Regio- and Enantioselective Oxytrifluoromethylthiolation of Aliphatic Internal Alkenes by Neighboring Group Assistance

Chiral selenide-catalyzed oxytrifluoromethylthiolation of aliphatic internal alkenes by a formally intermolecular strategy is disclosed, affording CF3S 1,3-amino alcohol and 1,3-diol derivatives with high regio-, enantio-, and diastereoselectivities. The reactions are promoted by a neighboring imide or ester group on substrates via a six-membered ring transition state. This assistance strategy is also successfully applied to the regio- and diastereoselective oxyhalofunctionalization of internal alkenes and the conversion of alkynes.

Structure-Odor Relationships of (Z)-3-Alken-1-ols, (Z)-3-Alkenals, and (Z)-3-Alkenoic Acids

(Z)-3-Unsaturated volatile acids, alcohols, and aldehydes are commonly found in foods and other natural sources, playing a vital role in the attractiveness of foods but also as compounds with chemocommunicative function in entomology. However, a systematic investigation of their smell properties, especially regarding humans, has not been carried out until today. To close this gap, the odor thresholds in air and odor qualities of homologous series of (Z)-3-alken-1-ols, (Z)-3-alkenals, and (Z)-3-alkenoic acids were determined by gas chromatography-olfactometry. It was found that the odor qualities in the series of the (Z)-3-alken-1-ols and (Z)-3-alkenals changed, with increasing chain length, from grassy, green to an overall fatty and citrus-like, soapy character. On the other hand, the odor qualities of the (Z)-3-alkenoic acids changed successively from cheesy, sweaty via plastic-like, to waxy in their homologous series. With regard to their odor potencies, the lowest thresholds in air were found for (Z)-3-hexenal, (Z)-3-octenoic acid, and (Z)-3-octenal.

Switchable Site-Selective Catalytic Carboxylation of Allylic Alcohols with CO2

A switchable site-selective catalytic carboxylation of allylic alcohols has been developed in which CO2 is used with dual roles, both facilitating C?OH cleavage and as a C1 source. This protocol is characterized by its mild reaction conditions, absence of stoichiometric amounts of organometallic reagents, broad scope, and exquisite regiodivergency which can be modulated by the type of ligand employed.

Regioselective Ni-Catalyzed Carboxylation of Allylic and Propargylic Alcohols with Carbon Dioxide

An efficient Ni-catalyzed reductive carboxylation of allylic alcohols with CO2 has been successfully developed, providing linear β,γ-unsaturated carboxylic acids as the sole regioisomer with generally high E/Z stereoselectivity. In addition, the carboxylic acids can be generated from propargylic alcohols via hydrogenation to give allylic alcohol intermediates, followed by carboxylation. A preliminary mechanistic investigation suggests that the hydrogenation step is made possible by a Ni hydride intermediate produced by a hydrogen atom transfer from water.

(E)-beta,gamma-alkenyl carboxylic acid derivative and preparation method thereof

The invention discloses an (E)-beta,gamma-alkenyl carboxylic acid derivative and a preparation method thereof. The preparation method disclosed by the invention comprises the following steps: in an organic solvent, under the condition that a nickel catalyst, a dinitrogen ligand, a reducer and an additive exist, carrying out a carboxylation reaction on an allyl alcohol substrate as shown in formula (II) and carbon dioxide. The preparation method disclosed by the invention is high in selectivity, the raw material reagents are easy to get and has high chemical selectivity and region selectivity, and the derivative is high in yield, high in purity, and low in generation cost and is more applicable for industrial production. (Refer to Specification).

A Facile Method for the Sulfenyllactonization of Alkenoic Acids Using Dimethyl Sulfoxide Activated by Oxalyl Chloride

A simple approach has been developed for the sulfenyllactonization of alkenoic acids using dimethyl sulfoxide activated with oxalyl chloride, in which methanesulfenyl chloride is proposed as the intermediate.

A 3 - methylthio - γ - method for preparing lactone (by machine translation)

The invention relates to shown in the following formula of 3 - methylthio - γ - method for preparing lactone: The method comprises the steps: aliphatic aldehyde with malonic acid in dimethyl sulfoxide in acetic acid piperidine salt under the catalytic action of the 100 °C the left and the right reaction, to obtain (E)- 3 - alkane olefine acid, yield 55 - 85%; in the - 78 - 10 °C will b a asian sulphone drop added to the oxalyl chloride in dichloromethane solution, then the (E)- 3 - alkane olefine acid added, at - 78 - 30 °C reaction, to obtain 3 - methylthio - γ - lactone, yield 60 - 82%. (by machine translation)