10488-95-6

Usage

Uses

Used in Food Industry:
Ethyl 3-oxooctanoate is used as a flavoring agent for imparting a fruity, pineapple-like taste to food products. It is particularly favored in the production of pineapple and other fruit-flavored beverages and confectionery, enhancing the overall flavor profile and consumer appeal.
Used in Fragrance Industry:
In the fragrance industry, ethyl 3-oxooctanoate is utilized as a component in perfumes and body care products. Its fruity, pineapple-like aroma adds a pleasant scent to these products, making them more attractive to consumers.
Used in Pharmaceutical Industry:
Ethyl 3-oxooctanoate serves as an intermediate in the synthesis of various pharmaceuticals. Its chemical properties make it a valuable building block for creating a range of medicinal compounds, contributing to the development of new drugs and therapies.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, ethyl 3-oxooctanoate is employed as an intermediate for the synthesis of different agrochemicals. Its role in creating effective and safe products for agricultural use highlights its importance in this industry.

Upstream product

• 110-43-0 n-pentyl methyl ketone 
• 141-52-6 sodium ethanolate 
• 105-58-8 Diethyl carbonate 
• 925-54-2 2-methylhexanal 
• 60988-34-3 1-(1-imidazolyl)-1-hexanone 
• 1071-46-1 hydrogen ethyl malonate 
• 62251-85-8 4-Ethyl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-octanoic acid ethyl ester 
• 7367-90-0 ethyl β-hydroxyoctanoate 
• 623-73-4 diazoacetic acid ethyl ester 
• 66-25-1 hexanal 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 142-61-0 Hexanoyl chloride 
• 109-65-9 1-bromo-butane 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 53939-85-8 6-pentyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 33796-86-0 3-hydroxyoctanoic acid 
• 15933-07-0 Ethyl 2-oxobutanoate 
• 13283-91-5 3-oxooctanoic acid 
• 13318-61-1 6-n-pentyluracil 
• 78672-90-9 methyl (R)-(-)-3-hydroxydecanoate 
• 98985-77-4 (2S,3R)-4-Methyl-5-oxo-2-pentyl-tetrahydro-furan-3-carboxylic acid 
• 98985-77-4 4-carboxy-4,5-dihydro-3-methyl-5-pentylfuran-2(3H)-one 
• 35087-30-0 5-pentyl-2,4-dihydro-3H-pyrazol-3-one 
• 44987-72-6 (R)-3-hydroxy-octanoic acid 
• 38862-65-6 2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester 
• 7367-90-0 ethyl β-hydroxyoctanoate 

Relevant academic research and scientific papers

Synthesis of coumarins by Pt-catalyzed hydroarylation of propiolic acids with phenols

Synthesis of coumarins from phenols and propiolic acids was examined by using a Pt catalyst such as PtCl2/AgOTf, K2PtCl4/AgOTf, and K2PtCl4/AgOAc. Propiolic acid reacted even with less reactive phenols in trifluoroacetic acid to give coumarins and dihydrocoumarins. In the case of substituted propiolic acids, phenylpropiolic acid and 2-octynoic acid, the reactions proceeded selectively to afford coumarins in good to high yields.

One-pot synthesis of β-keto esters and preparation of 3-ketopalmitoyl-CoA

β-Keto esters were synthesized from acyl chlorides and sodium ethyl acetoacetate in EtOH using a simple one-pot, one-step' method. The deacetylation of α-acetyl β-keto ester to β-keto ester was performed simply, by heating the reaction mixture at reflux for 12 hours, without the addition of additional reagents (e.g., NHl, NH MeOH, or NaOH). One of the β-keto esters prepared using this method was ethyl 3-oxohexadecanoate, a key intermediate in the synthesis of 3-ketopalmitoyl coenzyme A (3-oxohexadecanoyl coenzyme A), a potential substrate of the biologically important enzyme 17β-hydroxysteroid dehydrogenase type 12. Georg Thieme Verlag Stuttgart ? New York.

Isolation and crystal structures of both enol and keto tautomer intermediates in a hydration of an alkyne-carboxylic acid ester catalyzed by iridium complexes in water

Hydration of tetrolic acid ethyl ester as an alkyne-carboxylic acid ester catalyzed by an Ir-aqua complex [IrIIICp*(bpy)(OH 2)]2+ (1, Cp* = η5-C 5Me5, bpy = 2,2′-bipyridine) in water provides ethyl acetoacetate as a β-keto acid ester. We report the successful isolation of both an Ir-enol tautomer intermediate [IrIIICp*(bpy){CH 3C(OH)=CC(O)OC2H5}]+ (2) and an Ir-keto tautomer intermediate [IrIIICp*(bpy){CH 3C(O)-CHC(O)OC2H5}]+ (3) in the catalytic hydration by optimizing the conditions of the isolation, such as pH of the solution, reaction time, and selection of counteranions. The structures of the enol and keto complexes with characteristic Ir-(sp2carbon) bond and Ir-(sp3 carbon) bond, respectively, were unequivocally determined by X-ray analysis, IR, electrospray ionization mass spectrometry (ESI-MS), and NMR studies including 1H, 13C, distortionless enhancement by polarization transfer (DEPT) and correlation spectroscopy (COSY) experiments. It was confirmed that the hydration of tetrolic acid ethyl ester catalyzed by 2 or 3 as initial catalysts provides ethyl acetoacetate. Mechanism of the catalytic hydration of tetrolic acid ethyl ester as an alkyne-carboxylic acid ester is discussed based on isotopic labeling experiments with the Ir-enol and Ir-keto tautomers.

Simple synthesis of enantiomers of 6-hydroxyalkan-4-olides by stereoselective hydrogenation of methyl 4,6-dioxoalkanoates

A simple method for the synthesis of (S,S)- or (R,R)-6-hydroxyalkan-4-olides, components of the pheromonal secretion of the butterfly Idea leuconoe, in high ee by enantioselective hydrogenation of 4,6-diketo esters with a commercial available Ru-BINAP catalyst is described.

Molybdenum(VI) dichloride dioxide catalyzed synthesis of β-keto esters by C-H insertion of ethyl diazoacetate into aldehydes

Synthesis of β-keto esters by condensing various aldehydes with ethyl diazoacetate is achieved by using molybdenum(VI) dichloride dioxide. Aromatic, aliphatic, and heterocyclic aldehydes are successfully condensed with ethyl diazoacetate to obtain corresponding β-keto esters in high yields at room temperature.

Efficient Synthesis of Functionalized β-Keto Esters and β-Diketones through Regioselective Hydration of Alkynyl Esters and Alkynyl Ketones by Use of a Cationic NHC–AuICatalyst

Regioselective hydration of α-alkynyl esters and ketones by using a cationic NHC–AuIcatalyst results in β-keto esters and β-diketones, respectively. Controlled release of water in acetone by aldol self-condensation under the reaction conditions makes acetone as better solvent than 1,4-dioxane/water for the hydration of α-alkynyl esters having sensitive ester moieties.

Synthesis of 4-alkyl- and 4-(ω-chloroalkyl)-3-hydroxy-5- alkylidenebutenolides based on cyclizations of 4-alkyl- and 4-(ω- chloroalkyl)-1,3-bis(trimethylsilyloxy)buta-1,3-dienes with oxalyl chloride

4-Alkyl- and 4-(ω-chloroalkyl)-1,3-bis(trimethylsilyloxy)buta-1,3- dienes were prepared from ethyl acetoacetate in three steps. Their cyclization with oxalyl chloride allowed an efficient synthesis of 4-alkyl- and 4-(ω-chloroalkyl)-5-alkylidenebutenolides. Georg Thieme Verlag Stuttgart.

A novel convenient route to the naturally occurring 3-oxoacyl-L-homoserinelactones and related bacterial autoinducers

The naturally occurring 3-oxohexanoyl-L-homoserinelactone (1a), a bacterial autoinducer has been prepared in 47% overall yield by condensing stable 3-oxohexanoic acid (2), prepared by hydrolysis from the corresponding ester (3), with L-homoserinelactone using hydroxybenzotriazole (HOBT) and dicyclohexylcarbodiimide (DCC) in non-aqueous media.

Synthetic Scope of Br?nsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate

The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Br?nsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl-methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl ketones, the identity of two inseparable migrated products was confirmed by two-dimensional NMR spectroscopy.

Non-metal Lewis acid-catalyzed cross-Claisen condensation for β-keto esters

In this work, we disclose a new catalytic and highly chemoselective cross-Claisen condensation of esters. In the presence of TBSNTf2 as a non-metal Lewis acid, various esters can undergo cross-Claisen condensation to form β-keto esters which are important building blocks. Compared with the traditional Claisen condensation, this process, employing silyl ketene acetals (SKAs) as carbonic nucleophiles to achieve cross-Claisen condensation, requires mild conditions and has good tolerance of functional groups. This journal is