13088-48-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Oxoheptanoic acid is used as a reactant for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Oxoheptanoic acid is utilized as a reactant in the production of agrochemicals. Its properties make it suitable for the synthesis of compounds used in crop protection and other agricultural applications.
Used in Flavor and Fragrance Industry:
2-Oxoheptanoic acid is used as a flavor additive in the food and beverage industry. Its presence in natural sources such as cheese and wine contributes to the unique taste and aroma profiles of these products.
Used in Research and Development:
2-Oxoheptanoic acid is being researched for its potential applications in medical and biological processes. Its unique chemical properties and presence in natural sources make it an interesting candidate for further exploration in these fields.

Upstream product

• 111-14-8 oenanthic acid 
• 87378-94-7 diethyl 2-butyl-3-oxosuccinate 
• 64-19-7 acetic acid 
• 123-66-0 Ethyl hexanoate 
• 95-92-1 oxalic acid diethyl ester 
• 52358-05-1 2-hydroxyheptanoic acid 
• 13088-50-1 ethyl 2-oxoheptanoate 
• 693-25-4 n-pentylmagnesium bromide 
• 110-62-3 pentanal 
• 129661-87-6 pyruvic acid N,N-dimethylhydrazone 

Downstream Products

• 956155-26-3 pentanedicarbonyl chloride 
• 44902-01-4 (R)-2-aminoheptanoic acid 
• 78843-64-8 (2R)-heptane-1,2-diol 
• 4431-51-0 2-Butylmalonamid-saeure 
• 1615653-04-7 N-benzyl-N-(2-ethynylphenyl)-2-oxoheptanamide 
• 44902-02-5 (2S)-2-aminoheptanoic acid 
• 1115-90-8 2-aminoheptanoic acid 
• 13088-50-1 ethyl 2-oxoheptanoate 

Relevant academic research and scientific papers

Biocatalytic Oxidative Cascade for the Conversion of Fatty Acids into α-Ketoacids via Internal H2O2 Recycling

The functionalization of bio-based chemicals is essential to allow valorization of natural carbon sources. An atom-efficient biocatalytic oxidative cascade was developed for the conversion of saturated fatty acids to α-ketoacids. Employment of P450 monooxygenase in the peroxygenase mode for regioselective α-hydroxylation of fatty acids combined with enantioselective oxidation by α-hydroxyacid oxidase(s) resulted in internal recycling of the oxidant H2O2, thus minimizing degradation of ketoacid product and maximizing biocatalyst lifetime. The O2-dependent cascade relies on catalytic amounts of H2O2 and releases water as sole by-product. Octanoic acid was converted under mild conditions in aqueous buffer to 2-oxooctanoic acid in a simultaneous one-pot two-step cascade in up to >99 % conversion without accumulation of hydroxyacid intermediate. Scale-up allowed isolation of final product in 91 % yield and the cascade was applied to fatty acids of various chain lengths (C6:0 to C10:0).

Enzymatic Resolution of Chiral 2-Hydroxy Carboxylic Acids by Enantioselective Oxidation with Molecular Oxygen Catalyzed by the Glycolate Oxidase from Spinach (Spinacia oleracea)

The enzymatic oxidation of a variety of saturated and unsaturated aliphatic derivatives of racemic 2-hydroxy acids 1 to their 2-oxo acids 2 with molecular oxygen catalyzed by the glycolate oxidase from spinach (Spinacia oleracea) was shown to proceed highly enantioselectively.Thus, the glycolate oxidase-catalyzed kinetic resolution provides a convenient biocatalytic method for the preparation of enantiomerically pure (R)-2-hydroxy acids.The absolute configuration of the (R)-2-hydroxy acid 1b assigned by comparison of the measured optical rotation value with that of the literature data and by application of the exciton-coupled circular dichroism method (ECCD) on its bichromophoric 2-naphthoate 9-methylanthryl derivative 3b.These results establish the ECCD method as a convenient microscale chirooptic tool for the configurational assignment of 2-hydroxy acids.

Glucosinolate biosynthesis: Demonstration and characterization of the condensing enzyme of the chain elongation cycle in Eruca sativa

Glucosinolates are a group of sulfur-rich thioglucoside natural products common in the Brassicaceae and related plant families. The first phase in the formation of many glucosinolates involves the chain extension of the amino acid methionine. Additional methylene groups are inserted into the side chain of methionine by a three-step elongation cycle involving 2-oxo acid intermediates. This investigation demonstrated the first step of this chain elongation cycle in a partially-purified preparation from arugula (Eruca sativa). The 2-oxo acid derived from methionine, 4-methylthio-2-oxobutanoic acid, was shown to condense with acetyl-CoA to form 2-(2′-methylthioethyl)malate. The catalyst, designated as a 2-(ω-methylthioalkyl)malate synthase, belongs to a family of enzymes that mediate the condensation of acyl-CoAs with 2-oxo acids, including citrate synthase of the citric acid cycle, and 2-isopropylmalate synthase of leucine biosynthesis. The 2-(ω-methylthioalkyl)malate synthase studied here shares properties with other enzymes of this class, but appears chromatographically distinct and is found only in extracts of plant species producing glucosinolates from chain-elongated methionine derivatives. Although the principal glucosinolates of arugula are formed from methionine that has undergone two rounds of chain elongation to form dihomomethionine, studies with substrates and substrate analogs of different chain lengths showed that the isolated enzyme is responsible only for the condensation step of the first round of elongation.

Stereochemical Control on Yeast Reduction of α-Keto Esters. Reduction by Immobilized Bakers' Yeast in Hexane

Ethyl 2-oxoheptanoate has been reduced by three methods: free bakers' yeast (FBY) in water, immobilized bakers' yeast (IMBY) in water, and IMBY in hexane.It has been found that the stereochemistry of reduction of α-keto esters by bakers' yeast is controlled by appropiate choice of reaction conditions.

Amino acid stannous and application thereof in polyurethane foam

The invention relates to the field of chemical engineering, and relates to an organic tin catalyst, in particular to amino acid stannous and an application thereof in preparation of polyurethane foam. According to the method, firstly, pyruvic acid and aldehyde serve as raw materials, amino acid is synthesized through three steps, and then the amino acid reacts with stannous oxide to prepare the amino acid stannous. Compared with traditional stannous carboxylate, only carboxyl in the traditional stannous carboxylate is coordinated with a tin center, while amido and carboxyl in the amino acid stannous provided by the invention are coordinated with the tin center at the same time, so that the complex is more stable and higher in catalytic activity. In addition, the method for synthesizing the amino acid is not reported in public literatures, and the method is cheap in reagent, simpler in formula, more convenient to operate, green, safe, efficient, environmentally friendly and suitable for industrial production.

Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in Situ

We found that dioxiranes generated in situ from ketones 1-6 and Oxone underwent intramolecular oxidation of unactivated C-H bonds at δ sites of ketones to yield tetrahydropyrans. From the trans/cis ratio of oxidation products 1a and 2a as well as the retention of the configuration at the δ site of ketone 5, we proposed that the oxidation reaction proceeds through a concerted pathway under a spiro transition state. The intramolecular oxidation of ketone 6 showed the preference for a tertiary δ C-H bond over a secondary one. This intramolecular oxidation method can be extended to the oxidation of the tertiary γ′ C-H bond of ketones 9 and 10. For ketone 11 with two δ C-H bonds and one γ′ C-H bond linked respectively by a sp3 hydrocarbon tether and a sp2 ester tether, the oxidation took place exclusively at the δ C-H bonds. Finally, by introducing proper tethers, regioselective hydroxylation of steroid ketones 12-14 have been achieved at the C-17, C-16, C-3, and C-5 positions.

Method and product for skin lightening

A method and cosmetic product for lightening skin is provided, the method including wiping the skin with a cosmetic towelette. Impregnated on the towelette is an alpha-hydroxy carboxylic acid or salt thereof and a sunscreen agent.

Towelette product

A disposable towelette product is provided which includes a flexible water-insoluble substrate such as a tissue impregnated with an alpha- or beta-hydroxycarboxylic acid in a cosmetically acceptable carrier vehicle. Impregnated cosmetic composition in water will have a pH no higher than 6.8. A silicone microemulsion is present to minimize any stickiness resulting from deposition of the hydroxycarboxylic acid by the towelette onto the skin. In the presence of fatty acid group containing surfactants, the silicone microemulsion controls foul odors that the surfactants may emit through hydrolysis at low pH.

Towelette product for minimizing facial fine lines and wrinkles

A disposable towelette is provided which includes a flexible substrate such as a cellulosic tissue impregnated with an alpha-hydroxycarboxylic add delivered in a cosmetically acceptable carrier vehicle. There is further provided a method for cleansing skin and simultaneously inhibiting fine lines and wrinkles by wiping the skin with the impregnated towelette.

Palladium-Catalyzed Double and Single Carbonylations of β-Amino Alcohols. Selective Synthesis of Morpholine-2,3-diones and Oxazolidin-2-ones and Applications for Synthesis of α-Oxo Carboxylic Acids

Catalytic cross double carbonylation of secondary amines and alcohols proceeds in the presence of [PdCl2(MeCN)2] and CuI under carbon monoxide (80 atm) and oxygen (5 atm). Catalytic intramolecular double carbonylation of β-amino alcohols gives morpholine-2,3-diones, which are excellent protecting compounds of amino alcohols and important precursors for biologically active nitrogen compounds. In contrast, catalytic single carbonylation of β-amino alcohols under a mixture (1 : 1) of carbon monoxide and oxygen (1.0 atm) proceeds to give oxazolidin-2-ones selectively. The reaction can be explained by assuming a mechanism which includes intramolecular nucleophilic attack of the hydroxy group of (hydroxyethyl)aminocarbonyl ligands on the CO ligand of the carbamoylpalladium(II) complexes, followed by reductive elimination to give morpholine-2,3-diones. In contrast, direct nucleophilic attack of the hydroxy group to the carbamoyl group affords oxazolidin-2-ones. As a common intermediate for the double and single carbonylations, carbamoylpalladium(II) complex has been isolated by the reaction of [PdCl2(PMe3)2] with β-amino alcohol under CO. The present double carbonylation of amino alcohols provides a novel and convenient method for synthesis of α-oxo carboxylic acids. Thus, the morpholine-2,3-diones obtained undergo reaction with Grignard reagents chemoselectively at the ester positions to give 2-substituted 2-hydroxymorpholin-3-ones, which undergo acid hydrolysis to give α-oxo carboxylic acids.