Diethyl L-malate

Base Information

• Chemical Name: Diethyl L-malate
• CAS No.: 691-84-9
• Molecular Formula: C8H14O5
• Molecular Weight: 190.196
• Hs Code.: 29181990
• UNII: 6754Q2AK3B
• DSSTox Substance ID: DTXSID901044098
• Nikkaji Number: J15.076B
• Wikidata: Q27264072
• Mol file: 691-84-9.mol

Synonyms:691-84-9;Diethyl L-malate;Diethyl L-(-)-Malate;(S)-Diethyl 2-hydroxysuccinate;L-(-)-Malic Acid Diethyl Ester;L-Diethyl malate;Diethyl malate, L-;diethyl (2S)-2-hydroxybutanedioate;(S)-malic acid diethyl ester;diethyl (S)-malate;Diethyl (2S)-2-hydroxysuccinate;Diethyl (S)-(-)-2-hydroxysuccinate;UNII-6754Q2AK3B;L-(-)-Apple Acid Diethyl Ester;6754Q2AK3B;Butanedioic acid, 2-hydroxy-, 1,4-diethyl ester, (2S)-;2-hydroxy-butanedioic acid diethyl ester;Diethyl (2S)-malate;L-Malic acid diethyl ester;Butanedioic acid, hydroxy-, diethyl ester, (2S)-;SCHEMBL891003;(S)-Diethyl2-hydroxysuccinate;CHEBI:169284;DTXSID901044098;MFCD00210119;AKOS006238365;1,4-diethyl (2S)-2-hydroxybutanedioate;BS-23519;A9163;M1348;H11051;Diethyl (2S)-2-hydroxybutanedioate, AldrichCPR;EN300-7365668;Butanedioic acid, hydroxy-, diethyl ester, (S)-;Q27264072

Chemical Property of Diethyl L-malate

Chemical Property:

• Vapor Pressure: 0.000417mmHg at 25°C
• Melting Point: -168°C
• Refractive Index: 1.446
• Boiling Point: 281.6 °C at 760 mmHg
• PKA: 12.35±0.20(Predicted)
• Flash Point: 85 °C
• PSA: 72.83000
• Density: 1.149 g/cm³
• LogP: -0.13640
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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 L-(-)-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
• Isomeric SMILES: CCOC(=O)C[C@@H](C(=O)OCC)O
• Uses: Diethyl L-(-)-Malate is a reagent in the stereoselective synthesis of crucigasterin A and antitumor activity of crucigasterin A, B, and D.

Technology Process of Diethyl L-malate

There total 4 articles about Diethyl L-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:

diethyl oxaloacetate (108-56-5) → Diethyl (S)-malate (691-84-9) + ethyl 3-hydroxypropanoate (623-72-3)

Guidance literature:

With baker's yeast; for 24h; Ambient temperature;

DOI:10.1016/S0957-4166(99)00286-4

Reference yield:

ethanol (64-17-5) + (S)-Malic acid (97-67-6,78644-42-5) → Diethyl (S)-malate (691-84-9) + (S)-4-ethoxy-2-hydroxy-4-oxobutanoic acid (225933-67-5,15690-37-6)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 0.25h;

DOI:10.1080/09168451.2020.1743170

Reference yield:

ethanol (64-17-5) + 4-oxo-but-2-enoic acid ethyl ester (2960-66-9) → diethyl (R)-malate (7554-28-1) + Diethyl (S)-malate (691-84-9)

Guidance literature:

ethanol; 4-oxo-but-2-enoic acid ethyl ester; With dihydrogen peroxide; In chloroform; at -20 ℃; for 16h;

With N-ethyl-N,N-diisopropylamine; In chloroform; at 30 ℃; for 15h; Further stages. Title compound not separated from byproducts.;

DOI:10.1016/j.tetlet.2007.06.110

upstream raw materials:

diethyl oxaloacetate

sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate

ethanol

4-oxo-but-2-enoic acid ethyl ester

Downstream raw materials:

(S)-2-Trityloxy-succinic acid diethyl ester

diethyl (2S,3R)-3-benzoyloxymethyl-2-benzyloxymethoxysuccinate

3-benzyl 1,2-diethyl (1S,2R)-1-acetoxy-1,2,3-propanetricarboxylate

(S)-4-ethoxy-2-hydroxy-4-oxobutanoic acid

Refernces

• 1、 Zhao, Gui-Ling,Córdova, Armando. "A one-pot combination of amine and heterocyclic carbene catalysis: direct asymmetric synthesis of β-hydroxy and β-malonate esters from α,β-unsaturated aldehydes". . p. 5976 - 5980. Retrieved 2008/02/10.
• 2、 Santaniello, Enzo,Ferraboschi, Patrizia,Grisenti, Paride,Aragozzini, Fabrizio,Maconi, Elisabetta. "A Biocatalytic Approach to the Enantioselective Synthesis of (R)- and (S)-Malic Acid". . p. 601 - 605. Retrieved 2007/10/02.