2140-49-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Acetyl-3-oxobutanoic Acid is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to be metabolized and converted into other useful molecules.
Used in Metabolic Research:
In the field of metabolic research, 4-Acetyl-3-oxobutanoic Acid is utilized for studying the metabolic pathways of Penicillium species and the fermentation process of trihydroxybenzenes to acetate.
Used in Biochemical Analysis:
4-Acetyl-3-oxobutanoic Acid can be employed as a reference compound in biochemical analysis to understand its role in metabolic reactions and to develop methods for its detection and quantification.

Synthesis Reference(s)

Synthetic Communications, 20, p. 1931, 1990 DOI: 10.1080/00397919008053123

InChI:InChI=1/C6H8O4/c1-4(7)2-5(8)3-6(9)10/h2-3,8-10H,1H3/b5-2-

Upstream product

• 19841-57-7 ethyl 3,5-dioxohexanoate 
• 124-38-9 carbon dioxide 
• 123-54-6 acetylacetone 
• 26567-75-9 acetylacetone enol 
• 23652-85-9 (Z)-4-(methylamino)-3-penten-2-one 

Downstream Products

• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 541-50-4 2-acetoacetic acid 
• 64-19-7 acetic acid 

Relevant academic research and scientific papers

Photocatalytic carboxylation of organic substrates with carbon dioxide at zinc sulfide with deposited ruthenium nanoparticles

Photocatalytic carboxylation of acetylacetone with carbon dioxide has been performed by using ZnS-based photocatalysts. The formation of two isomeric carboxylic acids, as proven by IR and 13C NMR spectroscopy, was observed. The reaction yield was enhanced after deposition of ruthenium nanoparticles on ZnS. The reaction encompasses ruthenium-mediated one-electron reduction of CO2 to CO2.- with electrons from the conduction band of ZnS and one-hole oxidation of acetylacetone to the relevant radical. Coupling of photogenerated radicals leads to the formation of carboxylic acids. Generation of CO2.- has been confirmed by spin-trapping EPR measurements. The process described herein may find applications for the solar-light-driven green synthesis of Cn+1 carboxylic compounds from Cn substrates by utilising carbon dioxide. Dropping acid: Zinc sulfide with deposited ruthenium(0) nanoparticles photocatalyzes the carboxylation of acetylacetone with carbon dioxide as a substrate (see picture). The reaction proceeds through coupling of photogenerated R. and CO2.- radicals. Copyright

Reaction of dianions of acyclic β-enamino ketones with electrophiles. vii. synthesis of 5-(monoalkylamino)-3-oxo γ,δunsaturated acids and esters and of 3-(monoalkylamino)-5-oxo β,γ-unsaturated esters

Dianions of β-(monoalkylamino) α,β-unsaturated ketones react with carbon dioxide and diethyl carbonate leading to the title compounds. 2-alkyl-5-(monoalkylamino)-3-oxo γ,8-unsaturated acids are unstable and decarboxylate in a few hours after isolation. 3-(monoalkylamino)-5-oxo β,γ-unsaturated acids are never recovered from γ-dianions. Transmetallation from enaminone dianion to esters may occur. γ-Dianions require a non-nucleophilic base to obtain better results.

An Improved Method for γ-Carboxylation of β-Diketones. Synthesis of 4-Alkyl-3,5-dioxohexanoic Acids and 5-Alkyl Derivatives of Triacetic Acid Lactone

γ-Carboxylation of β-diketones, 1, can be improved using samples containing 100percent of ketoenol tautomers, 3, prepared by mild hydrolysis of the corresponding copper(II) complexes 2.Cyclization of the so formed 4-alkyl-3,5-dioxohexanoic acids, 4, affords 5-alkyl-4-hydroxy-6-methyl-2-pyrones, 5.

AN INVESTIGATION OF THE BIOSYNTHESIS OF CITROMYCETIN IN PENICILLIUM FREQUENTANS USING (13)C- AND (14)C-LABELLED PRECURSORS

Citromycetin (1) has been shown by (13)C n.m.r. to incorporate seven intact acetate units from -, -, and -acetates in accordance with a polyketide biosynthesis.The distribution of radioactivity following incorporation of malonate was consistent with the utilisation of two starter units.The following possible advanced precursors, labelled with (14)C, were not incorporated : 2,4-dihydroxy-6-methylbenzoic acid (14), 4,5,7-trihydroxyphthalide (16), and 4,7-dihydroxy-5-methylcoumarin (18).Two compounds, 2,4,5-trihydroxy-6-methylbenzoic acid (15) and triacetic acid lactone (17), were degraded to radiolabelled acetate prior to incorporation.