5746-90-7

Basic information

• Product Name: 3-METHYLGLUTACONIC ACID
• Synonyms: 3-METHYL-PENT-2-ENEDIOIC ACID;3-METHYLGLUTACONIC ACID;3-METHYL-2-PENTENEDIOIC ACID;3-Methyl-delta^2-penten-1,5-dioic acid;glutacouic acide 3-methyl;3-Methylglutaconic acid, mixture of E and Z isomers;NSC 249232;(E)-3-methylglutaconic acid
• CAS NO: 5746-90-7
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.13
• Mol File: 5746-90-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 115 °C
• Boiling Point: 399.4 °C at 760 mmHg
• Flash Point: 209.5 °C
• Appearance: /
• Density: 1.307 g/cm³
• Vapor Pressure: 1.71E-07mmHg at 25°C
• Refractive Index: 1.508
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.36±0.10(Predicted)
• Stability: Hygroscopic
• BRN: 1722907
• CAS DataBase Reference: 3-METHYLGLUTACONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLGLUTACONIC ACID(5746-90-7)
• EPA Substance Registry System: 3-METHYLGLUTACONIC ACID(5746-90-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 5746-90-7(Hazardous Substances Data)

Usage

Uses

3-Methylglutaconic acid is a glutarate which builds up in the urine in 3-methylglutaconic aciduria. 3-methylglutaconic aciduria is a term used to describe five different disorders that impair the functioning of energy-producing centers within cells (mitochondria)

Definition

ChEBI: A dicarboxylic acid comprising (E)-glutaconic acid carrying a 3-methyl substituent.

InChI:InChI=1/C6H8O4/c1-4(2-5(7)8)3-6(9)10/h2H,3H2,1H3,(H,7,8)(H,9,10)/b4-2+

Upstream product

• 924-59-4 diethyl 3-methylpent-2-enedioate 
• 480-65-9 isodehydracetic acid 
• 3385-34-0 ethyl isodehydroacetate 
• 141-97-9 ethyl acetoacetate 
• 19475-92-4 methyl 4-cyano-3-methylbut-3-enoate 
• 2381-87-5 4-methyl-5,6-dihydro-2H-pyran-2-one 
• 37028-26-5 5-acetyl-1,6-dihydroxy-4-methyl-2(1H)-pyridone 
• 130007-49-7 3-methyl-pentenedioic acid monoethyl ester 

Downstream Products

• 67116-19-2 3-methyl-pentenedioic acid anhydride 
• 372-42-9 (E)-3-methylpent-2-enedioic acid 
• 1610724-57-6 (1S,2R)-tert-butyl 5-methyl-2',3-dioxo-1-phenylspiro[cyclohex[4]ene-2,3'-indoline]-1'-carboxylate 
• 6247-73-0 S-(4-carboxy-3-methyl-but-2ξ-enoyl)-coenzyme-A 
• 52313-87-8 3-methyl-2-pentene-1,5-diacid dimethyl 
• 7470-42-0 3-acetyl-6-hydroxy-4-methyl-2H-pyran-2-one 
• 32013-63-1 2-acetylemodin 
• 18713-45-6 1,8-diacetoxy-3-methyl-anthraquinone 
• 518-80-9 helminthosporin 
• 481-74-3 Chrysophanol 
• 139542-31-7 6-(1'-hydroxy-2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)-4-methylpyran-2-one 
• 139542-29-3 4-methyl-6-(4',6',6'-trimethyl-2'-oxocyclohex-3'-enyl)pyran-2-one 
• 139542-30-6 4-methyl-6-(2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)pyran-2-one 
• 20110-02-5 (2Z,4E)-5-(1,4-Dihydroxy-2,6,6-trimethyl-cyclohex-2-enyl)-3-methyl-penta-2,4-dienoic acid 

Relevant articles and documents

Method for preparing dimethyl 3-methylpentyl-2-enedionate

The invention provides a method for preparing dimethyl 3-methylpentyl-2-enedionate. The method has the advantages of easy availability of raw materials, high yield and less waste residues, and is suitable for industrial production.

Allosteric effects in binuclear homo- and heterometallic triple-stranded lanthanide podates

This work illustrates a simple approach for deciphering and exploiting the various free energy contributions to the global complexation process leading to the binuclear triple-stranded podates [Ln2(L9)]6+ (Ln is a trivalent lanthanide). Despite the larger microscopic affinities exhibited by the binding sites for small Ln3+, the stability constants measured for [Ln2(L9)]6+ decrease along the lanthanide series; a phenomenon which can be ascribed to the severe enthalpic penalty accompanying the intramolecular cyclization around small Ln(III), combined with increasing anticooperative allosteric interligand interactions. Altogether, the microscopic thermodynamic characteristics predict β1,1,1 La,Lu,L9/β1,1,1Lu,La,L9 = 145 for the ratio of the formation constants of the target heterobimetallic [LaLu(L9)] 6+ and [LuLa(L9)]6+ microspecies, a value in line with the quantitative preparation (>90%) of [LaLu(L9)]6+ at millimolar concentrations. Preliminary NMR titrations indeed confirm the rare thermodynamic programming of a pure heterometallic f-f′ complex.

A Stereospecific Synthesis of (+/-)-Abscisic Acid

A convenient separation of (E)- and (Z)-3-methylpent-2-enedioic acids was devised, and it was shown that with acetyl chloride or thionyl chloride the (Z)-acid yields the cyclic anhydride while the (E)-acid forms 6-chloro-4-methylpyran-2-one.The chloropyranone by conventional chemistry gave 4-methyl-6-(2'-oxopropyl)pyran-2-one which condensed with 4-methylpent-3-en-2-one in the presence of pyrrolidine, yielding 4-methyl-6-(2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)pyran-2-one.Oxidation with selenium dioxide or t-butyl chromate then gave 6-(1'-hydroxy-2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)-4-methylpyran-2-one, which on reduction by lithium aluminium hydride and reoxidation afforded (+/-)-abscisic acid stereospecifically.