4144-54-1

Basic information

• Product Name: 4-Ketocapric acid
• Synonyms: 4-Ketocapric acid;4-Oxodecanoic acid
• CAS NO: 4144-54-1
• Molecular Formula: C₁₀H₁₈O₃
• Molecular Weight: 186.25
• Mol File: 4144-54-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Ketocapric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ketocapric acid(4144-54-1)
• EPA Substance Registry System: 4-Ketocapric acid(4144-54-1)

Safety Data

• Hazardous Substances Data: 4144-54-1(Hazardous Substances Data)

Usage

Uses

4-Oxodecanoic Acid is catalyzed by a novel carbonyl reductase from Serratia marcescens, SmCR, yield chiral γ- and δ-decalactones with high enantiopurity. It is one of the intermediate and minor compounds from the conversion of 12-Hydroxystearic Acid to 5-n-Hexyl-tetrahydrofuran-2-acetic Acid.Also, it is derived 4-Decanolide (D212553), which is one of the organic compounds from meat charbroiling operations studied.

Synthesis Reference(s)

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

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.