585-25-1

Usage

Uses

Used in Flavor Industry:
2,3-Octanedione is used as a flavor compound for enhancing or modifying the taste of various food products. Its unique "warmed-over" flavor can be utilized to create specific taste profiles or to mask undesirable flavors in the food industry.
Used in Chemical Research:
2,3-Octanedione serves as a valuable compound in chemical research and development. It can be used as a starting material or intermediate in the synthesis of more complex molecules, contributing to the advancement of various chemical and pharmaceutical applications.
Used in Analytical Chemistry:
In analytical chemistry, 2,3-Octanedione can be employed as a reference compound for the development and calibration of analytical methods, such as gas chromatography or mass spectrometry. Its distinct properties make it suitable for evaluating the performance of these techniques in detecting and quantifying specific compounds in complex mixtures.
Used in Food Safety and Quality Control:
2,3-Octanedione can be utilized in the food safety and quality control industry as a marker for the detection of rancidity or spoilage in various food products. Its "warmed-over" flavor may indicate the presence of off-flavors or the degradation of food quality, allowing for better monitoring and prevention of food spoilage.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 6338, 1994 DOI: 10.1021/jo00100a040

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

Upstream product

• 106-68-3 3-octanone 
• 4128-31-8 rac-octan-2-ol 
• 17257-80-6 Z-3,4-epoxy-2-octanone 
• 584-92-9 octane-2,3-dione 3-oxime 
• 23386-84-7 4-bromomethylene-5-pentyl-[1,3]dioxolane 
• 37163-97-6 erythro-2,3-octanediol 
• 108-24-7 acetic anhydride 
• 66-25-1 hexanal 
• 20653-90-1 threo-2,3-octanediol 
• 20653-90-1 (+/-)-2,3-octanediol 
• 37160-77-3 3-hydroxy-octan-2-one 
• 111-66-0 oct-1-ene 
• 15001-63-5 2-methyl-3-oxooctanal 
• 103941-98-6 2-methyloctane-1,3-diol 

Downstream Products

• 1182-13-4 octane-2,3-dione-bis-(2,4-dinitro-phenylhydrazone) 
• 66007-44-1 (+)-(2S,3R)-octane-2,3-diol 
• 86838-20-2 (+)-(3S)-3-hydroxyoctan-2-one 
• 84435-13-2 (+)-(2S)-2-hydroxyoctan-3-one 
• 83225-49-4 2,2,3,3-Tetrafluoro-octane 
• 84518-30-9 (-)-(2S,3S)-octane-2,3-diol 
• 152519-33-0 (S)-2-hydroxyhexan-⁽³⁾-one 

Relevant academic research and scientific papers

1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents

The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents

The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

2-Iodoxybenzoic acid mediated facile conversion of 1,3-diols to 1,2-diketones by oxidative cleavage of the C-C bond

1,3-Diols undergo smooth oxidative cleavage of the C-C bond in the presence of 2-iodoxybenzoic acid (IBX) affording 1,2-diketones in excellent yields under mild conditions. Georg Thieme Verlag Stuttgart.

Regio- and stereoselective reduction of diketones and oxidation of diols by biocatalytic hydrogen transfer

The asymmetric reduction of symmetrical and nonsymmetrical diketones as well as the stereoselective oxidation of various diols by biocatalytic hydrogen transfer was investigated by employing lyophilized cells of Rhodococcus ruber DSM 44541 containing alcohol dehydrogense ADH-'A'. Symmetrical and nonsymmetrical diketones at the (ω-1)- and (ω-2)-positions are reduced to the Prelog product with high stereopreference, while sterically more demanding ketone moieties, for example those at the (ω-3)-position, remain unchanged. For the oxidation mode, differentiation between primary and secondary alcohols is achieved, and the (S)-configured secondary alcohols at the (ω-1)- and (ω-2)-positions are oxidized preferentially. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Aroma compounds formed from 3-methyl-2,4-nonanedione under photooxidative conditions

The behavior of the prominent aroma compound 3-methyl-2,4-nonanedione under photooxidative conditions was investigated in a model experiment. The four well-known aroma compounds 2,3-butanedione, 2,3-octanedione, acetic acid, and caproic acid were identified. The main oxidation product was 3-hydroxy-3-methyl-2,4-nonanedione, an aroma compound with the odor description of rubbery, earthy, and plasticlike (GC-O). Its structure has been tentatively assigned based on mass (GC-MS) and vapor phase infrared spectra (GC-IR). The formal formation pathways are discussed for these compounds, and other origins described in the literature are presented.

Efficient oxidation of alcohols to carbonyl compounds with molecular oxygen catalyzed by N-hydroxyphthalimide combined with a Co species

Highly efficient catalytic oxidation of alcohols with molecular oxygen by N-hydroxyphthalimide (NHPI) combined with a Co species was developed. The oxidation of 2-octanol in the presence of catalytic amounts of NHPI and Co(OAc)2 under atmospheric dioxygen in AcOEt at 70 °C gave 2-octanone in 93% yield. The oxidation was significantly enhanced by adding a small amount of benzoic acid to proceed smoothly even at room temperature. Primary alcohols were oxidized by NHPI in the absence of any metal catalyst to form the corresponding carboxylic acids in good yields. In the oxidation of terminal vic-diols such as 1,2-butanediol, carbon-carbon bond cleavage was induced to give one carbon less carboxylic acids such as propionic acid, while internal vic-diols were selectively oxidized to 1,2-diketones.

A novel monoalkylation of symmetrical α-diones

An efficient method has been developed for the synthesis of monoalkylated 1.2-diones by using steric approach control. The dihydropyrazine 2 prepared from 2,3-butanedione and 1,2-diamino-2- methylpropane is selectively deprotonated on the less hindered methyl group to give an anion which is alkylated with alkyl iodides and activated bromides. In situ hydrolysis of the alkylated dihydropyrazines gives monoalkylated diones 4 in good yield.

Aerobic oxidation of alcohols to carbonyl compounds catalyzed by N-hydroxyphthalimide (NHPI) combined with Co(acac)3

Aerobic oxidation of various alcohols has been accomplished by using a new catalytic system. N-hydroxyphthalimide (NHPI) combined with Co(acac)3. The oxidation of alcohols by NHPI was found to be markedly enhanced by adding a slight amount of Co(acac)3 (0.05 equiv. to NHPI). Thus, secondary alcohols and vic-diols which are difficult to be oxidized by NHPI alone were smoothly oxidized with molecular oxygen (1 atm) to the corresponding carbonyl compounds under relatively mild conditions (65 ~ 75 °C).

A direct conversion of vic-diols into 1,2-diketones with aqueous hydrogen peroxide catalyzed by peroxotungstophosphate (PCWP)

α-Hydroxy ketones and vic-diols were successfully oxidized to the corresponding diketones with acqueous hydrogen peroxide in the presence of a catalytic amount of peroxotungstophosphate (PCWP). This method provides a straightforward route of 1,2-diketones which are difficult to prepare by conventional oxidation of vic-diols.