Diethyl malate

Base Information

• Chemical Name: Diethyl malate
• CAS No.: 7554-12-3
• Deprecated CAS: 121401-63-6,626-11-9
• Molecular Formula: C8H14 O5
• Molecular Weight: 190.196
• Hs Code.: 2918199090
• European Community (EC) Number: 210-930-0,231-444-5
• UNII: 59W97T99HI
• DSSTox Substance ID: DTXSID7048081
• Nikkaji Number: J44.123F
• Wikidata: Q27159562
• Metabolomics Workbench ID: 48913
• ChEMBL ID: CHEMBL3305989
• Mol file: 7554-12-3.mol

Synonyms:diethyl malate;diethyl malate, (+-)-isomer;diethyl malate, (R)-isomer;diethyl malate, (S)-isomer

Chemical Property of Diethyl malate

Chemical Property:

• Vapor Pressure: 0.000417mmHg at 25°C
• Refractive Index: 1.4330 to 1.4360
• Boiling Point: 122-124 ºC12 mm Hg(lit.)
• PKA: 12.35±0.20(Predicted)
• Flash Point: 185 ºF
• PSA: 72.83000
• Density: 1.128 g/mL at 25 ºC(lit.)
• LogP: -0.13640
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 190.08412354
• Heavy Atom Count: 13
• Complexity: 177

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diethyl DL-Malate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(C(=O)OCC)O

Technology Process of Diethyl malate

There total 31 articles about Diethyl malate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

ethanol (64-17-5) + malic acid (617-48-1,78644-42-5) → diethylmalate (7554-12-3)

Guidance literature:

With samarium(III) chloride; at 80 ℃; for 48h; sealed tube; Inert atmosphere;

DOI:10.1021/ol200247c

Reference yield: 86.0%

diethyl cis-epoxysuccinate → diethylmalate (7554-12-3)

Guidance literature:

With sodium phenylseleno(triethyl)borate; In ethanol; at 0 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(97)00781-3

Reference yield: 86.0%

diethyl cis-2,3-epoxybutane-1,4-dioate (3291-46-1,1035202-66-4) → diethylmalate (7554-12-3)

Guidance literature:

With sodium phenylseleno(triethyl)borate; In ethanol; at 0 ℃; for 0.166667h;

DOI:10.1246/cl.1988.507

upstream raw materials:

ethanol

malic acid

maleic acid

(2E)-but-2-enedioic acid

Downstream raw materials:

D,L-1,2,4-butanetriol

diethyl chlorosuccinate

diethyl 2-bromosuccinate

l(-)-Aepfelsaeure-dihydrazid

Refernces

• 1、 Portnova,Yamshchikova, Yu. F.,Krasnykh. "Retention Characteristics and Sorption Enthalpies of Esters of Natural Hydroxycarboxylic Acids on DB-1 Stationary Phase". . p. 577 - 583. Retrieved 2019/06/03.
• 2、 Fedorov,Bogdanov,Fadeev,Lagodzinskaya. "Synthesis and antiischemic activity of dicarboxylic nitroxyalkylamides and nitroxyalkylimides". . p. 1119 - 1125. Retrieved 2015/04/14.