626-51-7

Usage

Uses

Used in Coatings Industry:
3-Methylglutaric acid is used as a key component in the preparation method of high-adhesion super weather-resistant powder coatings. Its chemical properties contribute to the enhanced adhesion and weather resistance of these coatings, making them ideal for various applications where durability and protection from environmental elements are required.

Purification Methods

Crystallise the acid from distilled water, then dry it under vacuum over conc H2SO4. [Beilstein 2 IV 1992.]

InChI:InChI=1/C6H10O4/c1-4(2-5(7)8)3-6(9)10/h4H,2-3H2,1H3,(H,7,8)(H,9,10)/p-2

Upstream product

• 64190-48-3 dihydro-4-methyl-2(3H)-furanone 
• 151-50-8 potassium cyanide 
• 4341-24-6 5-methylcyclohexan-1,3-dione 
• 89-82-7 pulegone 
• 5405-41-4 ethyl 3-hydroxybutyrate 
• 18852-51-2 sodium cyanoacetic acid ethyl ester 
• 7425-49-2 ethyl 3-bromobutanoate 
• 996-82-7 sodium diethylmalonate 
• 65562-58-5 3,7-dimethyl-oct-5-enoic acid 
• 5447-66-5 2,4-dicyano-3-methyl-glutaric acid diamide 
• 7425-48-1 3-chloro-butyric acid ethyl ester 
• 32091-48-8 β-Methylglutaronitrile 
• 6280-15-5 3-methylpentanedial 
• 90423-57-7 3-methylene-glutaric acid 

Downstream Products

• 4166-53-4 3-methylglutaric anhydride 
• 27151-65-1 3-methyl-1,5-pentanedioic acid monomethyl ester 
• 19013-37-7 dimethyl 3-methylglutarate 
• 6829-42-1 diethyl 3-methylglutarate 
• 376-94-3 3-Methyl-glutarsaeure-bis-<2,2,3,3,4,4,5,5-octafluor-pentylester> 
• 424-24-8 3-methyl-glutaric acid bis-(1H,1H-undecafluoro-hexyl ester) 
• 4457-71-0 3-methylpentane-1,5-diol 
• 861372-81-8 2-bromo-3-methyl-glutaric acid dimethyl ester 
• 107-87-9 2-Pentanone 
• 108-39-4 3-methyl-phenol 
• 67-64-1 acetone 
• 591-24-2 3-Methylcyclohexanone 
• 4751-49-9 dimethyl 4-methylheptanedioate 
• 72692-98-9 3-methyl-pentane-1,2,5-triol 

Relevant academic research and scientific papers

Sustainable electroorganic synthesis of lignin-derived dicarboxylic acids

The oxidative ring opening of lignin-derived alkylated cyclohexanols to bio-based alkylated dicarboxylic acids is successfully performed by an electrocatalytic conversion. To establish this transformation as a green method, we developed a simple protocol for the anodic oxidation at nickel oxide-hydroxide (NiOOH) foam anodes in caustic soda in both a batch and flow electrolysis approach.

Method for synthesizing muscone by utilizing beta-monomethyl methylglutarate

The invention discloses a method for synthesizing muscone by utilizing beta-monomethyl methylglutarate. According to the method, beta-monomethyl methylglutarate and alpha,omega-dodecanedioic acid monomethyl ester respectively prepared through a heteropoly acid catalytic transesterification method are used as raw materials, and Kolbe electrolysis, acyloin condensation and reduction reaction are performed to prepare the muscone. The method of the present invention has advantages of high raw material utilization rate, mold condition, easy control and environmental protection, and is suitable for industrial production .

A new method for the preparation of non-terminal alkynes: Application to the total syntheses of tulearin A and C

Lactones are known to react with the reagent generated in situ from CCl4 and PPh3 in a Wittig-type fashion to give gem-dichloro-olefin derivatives. Such compounds are now shown to undergo reductive alkylation on treatment with organolithium reagents RLi to furnish acetylene derivatives bearing the substituent R at their termini (R=Me, n-, sec-, tert-alkyl, silyl); the reaction can be catalyzed with either Cu(acac)2 or Fe(acac)3/1,2-diaminobenzene. Two alkynol derivatives prepared in this way from readily accessible lactone precursors served as the key building blocks for the total syntheses of the cytotoxic marine macrolides tulearin A (1) and C (2). The assembly of these fragile targets hinged upon ring closing alkyne metathesis (RCAM) followed by a formal trans-reduction of the resulting cycloalkynes via trans-hydrosilylation/protodesilylation.

Two potent OXE-R antagonists: Assignment of stereochemistry

5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is formed by the oxidation of 5-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-HETE), which is a major metabolite of enzymatic oxidation of arachidonic acid (AA). 5-Oxo-ETE is the most potent lipid chemoattractant for human eosinophils. Its actions are mediated by the selective OXE receptor, which is therefore an attractive target in eosinophilic diseases such as allergic rhinitis and asthma. Recently, we have reported two excellent OXE receptor antagonists that have IC50 values at low nanomolar concentrations. Each of these antagonists has a chiral center, and the isolation of the individual enantiomers by chiral high-performance liquid chromatography (HPLC) revealed that in each case one enantiomer is over 300 times more potent than the other. To unambiguously assign the stereochemistry of these enantiomers and to provide access to larger amounts of the active compounds for biological testing, we report here their total synthesis.

Total synthesis of tulearin C

With the help of the smaller brother: Although alkyne metathesis will always be the little brother of alkene metathesis, it allows problems to be solved that are currently beyond reach of the more famous sibling. This notion is exemplified by the tulearin macrolides, which could only be selectively forged by ring-closing alkyne metathesis (RCAM)/transreduction using the latest generation of alkyne metathesis catalysts.

Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones

Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species.

Process for the preparation of carboxylic acids and derivatives of them

The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula STR1 wherein R means hydrogen, or a C1-4 alkyl or a (C1-5 alkoxy)carbonyl group, R1 is as defined in claim 1, R7 stands for hydrogen or a C1-7 alkyl group and R8 means hydrogen or a carboxyl group, by reacting a 1,3-dioxane-4,6-dione derivative of the general formula STR2 wherein R9 stands for a C1-4 alkyl group or a phenyl group, optionally monosubstituted by halogen and R10 stands for hydrogen or a C1-5 alkyl group or R9 and R10 together form a pentamethylene group, and an aldehyde or ketone of the general formula STR3 in the presence of formic acid.

Process for the preparation of carboxylic acids and derivatives of them

The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula wherein Rmeans hydrogen, or a C1 4alkyl or a (C1 5alkoxy)carbonyl group, R1is as defined in claim 1, R7stands for hydrogen or a C1 7alkyl group and R8means hydrogen or a carboxyl group, by reacting a 1,3-dioxane-4,6-dione derivative of the general formula wherein R9stands for a C1 4alkyl group or a phenyl group, optionally monosubstituted by halogen and R10stands for hydrogen or a C1 5alkyl group or R9 and R10together form a pentamethylene group, and an aldehyde or ketone of the general formula in the presence of formic acid and of [a] amine(s) and, if desired, of an alcohol of the general formula, , R7 - OH VI,, , wherein R7is a C1 7alkyl group, at a temperature of 20 to 140°C, and/or, reducing an unsaturated 1,3-dioxane-4,6-dione derivative of the general formula and/or, a 1,3-dioxane-4,6-dione derivative of the general formula with formic acid in the presence of [a] amine(s) and, if desired, of an alcohol as above defined.

SYNTHESIS OF 3-METHYLGLUTARIC ACID

4-Methyltetrahydropyran has been synthetized by catalytic hydrogenation of a mixture of the isomeric 4-methyl-5,6-dihydro- and 4-methylenetetrahydropyrans.Oxidative degradation then led to 3-methylglutaric acid.