372-42-9

Basic information

• Product Name: 2-Pentenedioic acid, 3-methyl-, (E)-
• CAS NO: 372-42-9
• Molecular Formula: C6H8O4
• Molecular Weight: 144.127
• Mol File: 372-42-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-Pentenedioic acid, 3-methyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pentenedioic acid, 3-methyl-, (E)-(372-42-9)
• EPA Substance Registry System: 2-Pentenedioic acid, 3-methyl-, (E)-(372-42-9)

Safety Data

• Hazardous Substances Data: 372-42-9(Hazardous Substances Data)

Upstream product

• 130007-49-7 3-methyl-pentenedioic acid monoethyl ester 
• 3385-34-0 ethyl isodehydroacetate 
• 372-42-9 3-methylpent-2-enedioic acid 
• 7647-01-0 hydrogenchloride 
• 108487-40-7 3-methyl-pentenedinitrile 
• 2381-87-5 4-methyl-5,6-dihydro-2H-pyran-2-one 
• 141-97-9 ethyl acetoacetate 
• 37028-26-5 5-acetyl-1,6-dihydroxy-4-methyl-2(1H)-pyridone 
• 19475-92-4 methyl 4-cyano-3-methylbut-3-enoate 
• 480-65-9 isodehydracetic acid 
• 924-59-4 diethyl 3-methylpent-2-enedioate 

Downstream Products

• 67116-19-2 3-methyl-pentenedioic acid anhydride 
• 52313-87-8 3-methyl-2-pentene-1,5-diacid dimethyl 
• 6247-73-0 S-(4-carboxy-3-methyl-but-2ξ-enoyl)-coenzyme-A 
• 1610724-57-6 (1S,2R)-tert-butyl 5-methyl-2',3-dioxo-1-phenylspiro[cyclohex[4]ene-2,3'-indoline]-1'-carboxylate 
• 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 
• 21293-29-8 (2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic acid 

Relevant articles and documents

An improved synthesis of a mixture of diethyl (Z)- and (E)-3-methylglutaconates from ethyl acetoacetate

A simple, efficient two-step synthesis of a mixture of diethyl (Z)- and (E)-3-methylglutaconates from isodehydroacetic acid in 83% yield is described. On the basis of this synthesis an improved procedure for the preparation of a mixture of (Z)- and (E)-3-methylglutaconic acids from ethyl acetoacetate in 44% overall yield was elaborated.

POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES

Described herein polymer precursor compounds (aka polymer building blocks) of derived from biobased compounds, and specifically biobased mevalonolactone and its related derivatives. Through oxidation these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols and polyamides, as well as precursors for glycidyl esters and omega-alkenyl esters. Through reduction, these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols, polycarbonates, as well as precursors for glycidyl ethers and omega-alkenyl ethers. Through nucleophilic ring opening and/or amidation, these biobased precursors can be reacted to yield building blocks for polyester polyols, chain-extender for polyurethanes, or polyester-amides.

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.