4144-54-1

Usage

Uses

Used in Flavor and Fragrance Industry:
4-Ketocapric acid is used as a precursor for the synthesis of chiral γand δ-decalactones with high enantiopurity. These lactones are valuable in the flavor and fragrance industry for creating natural and complex scents in various products.
Used in Chemical Synthesis:
4-Ketocapric acid is utilized as an intermediate compound in the conversion process of 12-Hydroxystearic Acid to 5-n-Hexyl-tetrahydrofuran-2-acetic Acid. This conversion is significant in the chemical industry for producing various organic compounds with diverse applications.
Used in Food Industry:
Derived from meat charbroiling operations, 4-Decanolide (D212553), which is related to 4-Ketocapric acid, is one of the organic compounds studied for its potential impact on the flavor and aroma of cooked meat products. This application highlights the importance of 4-Ketocapric acid in understanding and enhancing the sensory qualities of food.

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 616, 1966 DOI: 10.1021/jo01340a521

Upstream product

• 111-66-0 oct-1-ene 
• 2082-76-0 capric anhydride 
• 106-14-9 R-12-hydroxyoctadecanoic acid 
• 334-48-5 1-decanoic acid 

Downstream Products

• 706-14-9 5-hexyldihydro-2(3H)-furanone 
• 334-48-5 1-decanoic acid 
• 7011-82-7 methyl 4-oxodecanoate 
• 7018-92-0 2,5-Undecanedione 
• 63095-33-0 γ-(Z)-dec-7-enlactone 
• 1128-08-1 dihydro-cis-jasmone 
• 69830-91-7 (R)-4-dodecanolide 
• 107797-26-2 (R)-5-Hexyl-dihydro-furan-2-one 

Relevant academic research and scientific papers

Reactions of Dioxiranes with Selected Oleochemicals

Reaction of fatty acids with dimethyldioxirane in acetone produces ketoacids in 9-12percent yields in which the ketone carbonyl is distributed along the fatty chain.The n-1 position appears to be preferred.Lactones of hydroxy fatty acids are oxidized by this reagent, but in low yields, to the corresponding ketoacids.Biphasic epoxidations with methylethyldioxirane in 2-butanone were conducted with methyl oleate and methyl ricinoleate to give the corresponding epoxides in high yield, and olive oil and tallow were cleanly epoxidized by this procedure as well.KEY WORDS: Chain functionalization, dioxirane, epoxidation, oleic acid, ricinoleic acid, tallow.

Microbial Transformation of 12-Hydroxyoctadecanoic Acid to 5-n-Hexyl-Tetrahydrofuran-2-Acetic Acid

Stationary-phase cells of a corynebacterium (FUI-2) and a bacillus (NRRL B-14864) isolate, when grown aerobically in 1percent YE medium at 25 deg C, converted 12-hydroxystearic acid to a major compound, 5-n-hexyl-tetrahydrofuran-2-acetic acid, and other intermediate and minor compounds (6-hydroxydodecanoic acid, 4-hydroxydecanoic acid, 4-ketodecanoic acid and γ-decanolactone).The yields of 5-n-hexyl-tetrahydrofuran-2-acetic acid, 4-hydroxydecanoic acid, and γ-decanolactone, by Bacillus lentus NRRL B-14864 were 43percent, 18percent and 5percent, respectively, after 2.5 d of incubation. Key Words: Bacillus lentus, corynebacterium, D-(+)-12-hydroxy-octadecanoic acid, D-(+)-12-hydroxystearic acid, γ-decanolactone, 4-hydroxydecanoic acid, 6-hydroxydodecanoic acid, 4-ketodecanoic acid, 5-n-hexyl-tetrahydrofuran-2-acetic acid.

FACTORS GOVERNING PRODUCT DISTRIBUTION IN THE OXIDATION OF ALKENES BY MANGANESE(III) ACETATE IN ACETIC ACID AND ACETIC ANHYDRIDE

A systematic investigation has been carried out into the effect of different reaction parameters on the oxidation of oct-1-ene by manganese(III) acetate in acetic acid and acetic anhydride.The most important factor in dictating the ratio of products is the composition of the solvent.In the absence of anhydride γ-decanolactone is virtually the sole product.Even small quantitites of anhydride lead to the lactone being replaced by other products derived from cationic intermediates C6H13CH(1+)CH2COX (X = OH or OAc).Further increases in the amount of anhydride encourage the formation of decanoic acid until, in 90percent anhydride, this becomes the predominant product.The results cannot be interpreted simply in terms of competition for the alkene by the radicals (.)CH2CO2H and (.)CH2COOCOCH3.Decanoic acid formation is also favoured by low temperatures, low concentration of oxidants, and by the addition of acetate ions.A comparision is made of the efficiency of addition when the initiating species is manganese(III) or a peroxide.