5455-24-3

Basic information

• Product Name: 4,5-Octanedione
• Synonyms: Bibutyryl;4,5-Octadione
• CAS NO: 5455-24-3
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.2
• Mol File: 5455-24-3.mol

Chemical Properties

• Melting Point: 14.93°C (estimate)
• Boiling Point: 168.05°C
• Flash Point: 56.5°C
• Appearance: /
• Density: 0.9340
• Vapor Pressure: 1.65mmHg at 25°C
• Refractive Index: 1.4559 (estimate)
• CAS DataBase Reference: 4,5-Octanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Octanedione(5455-24-3)
• EPA Substance Registry System: 4,5-Octanedione(5455-24-3)

Safety Data

• Hazardous Substances Data: 5455-24-3(Hazardous Substances Data)

Usage

Uses

Used in Food and Beverage Industry:
4,5-Octanedione is used as a flavoring agent for its ability to provide a buttery or creamy taste to various food and beverage products. Its application enhances the sensory experience of consumers by mimicking the flavor of dairy products without the use of actual dairy ingredients.
Despite its widespread use in the food and beverage industry, there is an ongoing effort to limit the use of 4,5-Octanedione due to the associated health risks. The respiratory issues linked to its exposure, especially in workers at microwave popcorn factories, have raised concerns about its safety. As a result, alternative flavoring agents are being explored to reduce the reliance on diacetyl and mitigate the potential health hazards associated with its use.

InChI:InChI=1/C8H14O2/c1-3-5-7(9)8(10)6-4-2/h3-6H2,1-2H3

Upstream product

• 105-54-4 butanoic acid ethyl ester 
• 123-72-8 butyraldehyde 
• 141-75-3 butyryl chloride 
• 1942-45-6 4-Octyne 
• 2432-51-1 ethylthioacetic acid methyl ester 
• 22520-40-7 (4S*,5S*)-octane-4,5-diol 
• 592-99-4 4-octene 
• 67-56-1 methanol 
• 108-24-7 acetic anhydride 
• 142-96-1 dibutyl ether 
• 60-29-7 diethyl ether 
• 201230-82-2 carbon monoxide 
• 75-19-4 cyclopropane 
• 286-20-4 cyclohexane-1,2-epoxide 

Downstream Products

• 86628-42-4 3-p-Nitrophenyl-5,6-di-n-propylimidazo<2,1-b>thiazole 
• 86628-34-4 3-Biphenyl-4-yl-5,6-dipropyl-imidazo[2,1-b]thiazole 
• 86628-41-3 2-p-Nitrophenacylthio-4,5-di-n-propylimidazole 
• 86628-29-7 1-Biphenyl-4-yl-2-(4,5-dipropyl-1H-imidazol-2-ylsulfanyl)-ethanone 
• 86628-35-5 3-Phenyl-5,6-dipropyl-imidazo[2,1-b]thiazole 
• 86628-30-0 2-(4,5-Dipropyl-1H-imidazol-2-ylsulfanyl)-1-phenyl-ethanone 
• 107-92-6 butyric acid 
• 496-77-5 butyroin 
• 22520-41-8 meso-4,5-octanediol 
• 22520-40-7 syn-4,5-octanediol 
• 25379-20-8 2-phenylindolizine 
• 83260-60-0 2,3-Dipropyl-quinolizinylium; bromide 
• 3639-22-3 2,2-dipropylglycolic acid 

Relevant articles and documents

Sol-gel synthesis of ceria-zirconia-based high-entropy oxides as high-promotion catalysts for the synthesis of 1,2-diketones from aldehyde

Efficient Lewis-acid-catalyzed direct conversion of aldehydes to 1,2-diketones in the liquid phase was enabled by using newly designed and developed ceria–zirconia-based high-entropy oxides (HEOs) as the actual catalysts. The synergistic effect of various cations incorporated in the same oxide structure (framework) was partially responsible for the efficiency of multicationic materials compared to the corresponding single-cation oxide forms. Furthermore, a clear, linear relationship between the Lewis acidity and the catalytic activity of the HEOs was observed. Due to the developed strategy, exclusively diketone-selective, recyclable, versatile heterogeneous catalytic transformation of aldehydes can be realized under mild reaction conditions.

Rhenium-catalyzed didehydroxylation of vicinal diols to alkenes using a simple alcohol as a reducing agent

A new method for the catalytic didehydroxylation of vicinal diols is described. Employing a readily available low-valent rhenium carbonyl complex and a simple alcohol as a reducing agent, both terminal and internal vicinal diols are deoxygenated to olefins in good yield. The optional addition of acid (TsOH, H2SO4) provides access to lower reaction temperatures. This new system enables the transformation of a four-carbon sugar polyol into an oxygen-reduced compound, providing promising evidence for its practical application to produce unsaturated compounds from biomass-derived materials.

Product selectivity in the electroreduction of thioesters

The electroreduction of differently substituted aromatic and aliphatic thioesters (RCOSR′) led to regioselective reactions depending on the nature of the substituents. Thus, the cleavage between the carbonyl group and the SR′ group afforded α-diketones an

Ruthenium-Catalyzed Oxidative Cleavage of Alkynes to Carboxylic Acids

We describe an efficient method for the oxidative cleavage of alkynes to carboxylic acids using a combination of RuO2/Oxone/NaHCO3 in a CH3CN/H2O/EtOAc solvent system. Both internal and terminal alkynes, regardless of their electron density, can be oxidized to carboxylic acids in excellent yield (up to 99%). 1H NMR spectroscopy and ESI-MS experiments provided evidence for α-diketones and anhydrides as possible intermediates in these oxidation reactions.

Lewis acid assisted permanganate oxidations

Lewis acids combine with permanganate in acetone solutions to form a complex that has enhanced oxidizing capabilities. The use of Lewis acids under these conditions to promote permanganate oxidations is superior to the use of Bronsted acids because the latter promote enolization of the solvent and subsequent unproductive reduction of the oxidant. The products obtained from a variety of alkenes, alkynes, arenes, sulfides, alcohols and ethers have been identified and probable reaction mechanisms proposed.

Oxidation of alkylphenylacetylenes and dialkylacetylenes on palladium catalysts in DMSO

Alkylphenyl-and dialkylacetylenes are oxidized by the DMSO-PdCl2 or DMSO-Pd/C system to give the corresponding 1,2-diketones. Oxidation of these compounds, unlike that of diarylacetylenes, is less selective and is accompanied by the partial cle

Oxidation of Alkynes by Hydrogen Peroxide Catalyzed by Methylrhenium Trioxide

The oxidation of alkynes with hydrogen peroxide is catalyzed by methylrhenium tioxide.The reactions can be rationalized by postulating that an oxirene intermediate is formed between a rhenium peroxide and the alkyne.Internal alkynes yield α-diketones and carboxylic acids, the latter from the complete cleavage of the triple bonds.Rearrangement products were observed only for aliphatic alkynes.Terminal alkynes gave carboxylic acids and their derivatives and α-keto acids as the major products, but their yields varied with the solvent used.

Cobalt(II)-Catalyzed Reaction of Aldehydes with Acetic Anhydride under an Oxygen Atmosphere: Scope and Mechanism

The reaction of aldehydes with acetic anhydride in the presence of catalytic cobalt(II) chloride under an oxygen atmosphere at ambient temperature is dependent upon the reaction medium.Aliphatic aldehydes react in acetonitrile to give 1,2-diones whereas the aromatic aldehydes are acylated to yield the corresponding acylals.On the other hand, carboxylic acids are obtained from aliphatic and aromatic aldehydes by conducting the reaction in dichloroethane or benzene.Cobalt(II) chloride in acetonitrile catalyzes the conversion of aliphatic aldehydes to the correspondinganhydrides in the absence of acetic anhydride whereas aromatic aldehydes remain largely unaffected under these conditions.A preliminary mechanistic study in three different solvents (i.e. acetonitrile, dichloroethane, and DMF) has revealed that in acetonitrile and in the presence of acetic anhydride, aliphatic aldehydes behave differently than aromatic aldehydes.Some trapping experiments using methyl acrylate and stilbene have been conducted to demonstrate the occurence of an acyl cobalt and peroxyacyl cobalt intermediate during these reactions.

Cobalt(II)chloride catalysed cleavage of ethers with acyl halides: Scope and mechanism

Cobalt(II) chloride in acetonitrile catalyses the cleavage of a wide variety of ethers with acyl halides under mild conditions to give the corresponding esters in good yields. Acyclic aliphatic ethers are cleaved to the corresponding ester and chlorides whereas the cyclic aliphatic ethers give rise to the ω-chloroesters. The benzyl ethers can be converted to the corresponding esters along with the formation of benzyl chloride and benzyl acetamide. A comparative study for the cleavage of allyl and benzyl ether has revealed that benzyl ether can be selectively cleaved in presence of the allyl ethers. The oxiranes can be cleaved in highly regioselective manner to the corresponding-β-chloroesters. The vinyl ethers undergo sp2-hybridised carbon-oxygen bond cleavage under these conditions. Based on product analysis, a mechanism involving electron transfer followed by O-acylation and S(N)1 or S(N)2 attack by chloride-ion is discussed.