cis-Epoxysuccinic acid

Base Information

• Chemical Name: cis-Epoxysuccinic acid
• CAS No.: 16533-72-5
• Molecular Formula: C4H4O5
• Molecular Weight: 132.073
• Hs Code.: 2918990090
• European Community (EC) Number: 240-604-3
• DSSTox Substance ID: DTXSID401016953,DTXSID701016952
• Nikkaji Number: J27.177B
• Pharos Ligand ID: 4YFK22F4QJLG
• ChEMBL ID: CHEMBL1741775
• Mol file: 16533-72-5.mol

Synonyms:cis-Epoxysuccinic acid;16533-72-5;(2R,3S)-oxirane-2,3-dicarboxylic acid;2,3-Oxiranedicarboxylic acid, (2R,3S)-rel-;cis-2,3-Oxiranedicarboxylic acid;MFCD00191645;Epoxymaleic acid;(2S,3R)-oxirane-2,3-dicarboxylic acid;Cis-poxysuccinic acid;NSC-43234;cis-2,3 expoxysuccinate;Succinic acid, epoxy-, cis-;GTPL9631;SCHEMBL4466386;CHEMBL1741775;DCEMCPAKSGRHCN-XIXRPRMCSA-N;DTXSID401016953;DTXSID701016952;Cis-oxirane-2,3-dicarboxylic acid;cis-AthylenoxiddicarbonsA currencyure;GEO-01295;NCGC00013522;AKOS005258282;(2R,3S)-2,3-Oxiranedicarboxylic acid;NCGC00013522-02;NCGC00096635-01;AS-65405;HY-125791;CS-0099343;E0449;2,3-Oxiranedicarboxylicacid, (2R,3S)-rel-;D90518;A882397;W-200155;2222820-55-3;U9S

Chemical Property of cis-Epoxysuccinic acid

Chemical Property:

• Appearance/Colour: Slightly beige crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 148-149 °C
• Boiling Point: 467.5 °C at 760 mmHg
• PKA: pK1:1.93;pK2:3.92 (25°C)
• Flash Point: 215.7 °C
• PSA: 87.13000
• Density: 1.92 g/cm³
• LogP: -1.07700
• Solubility.: soluble in Methanol
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 132.00587322
• Heavy Atom Count: 9
• Complexity: 144

Purity/Quality:

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

cis-Epoxysuccinic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-22
• Safety Statements: 45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1(C(O1)C(=O)O)C(=O)O
• Isomeric SMILES: [C@@H]1([C@H](O1)C(=O)O)C(=O)O
• Uses: cis-Epoxysuccinic Acid is a substrate for cis-epoxysuccinic acid hydrolase from Nocardia tartarican.

Technology Process of cis-Epoxysuccinic acid

There total 16 articles about cis-Epoxysuccinic acid 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: 97.0%

(2SR,3SR)-oxirane-2,3-dicarboxylic acid diethyl ester (3291-46-1,3291-47-2,61937-48-2,66647-17-4,73890-18-3,74243-85-9) → DL-trans-epoxysuccinic acid (141-36-6,3272-11-5,16533-72-5,17015-08-6,17087-75-1,22734-83-4)

Guidance literature:

With sodium hydroxide; In methanol; at 0 - 20 ℃; for 1.5h;

DOI:10.1021/jm0305016

Reference yield: 55.0%

(2E)-but-2-enedioic acid (110-17-8,26099-09-2) → DL-trans-epoxysuccinic acid (141-36-6,3272-11-5,16533-72-5,17015-08-6,17087-75-1,22734-83-4)

Guidance literature:

(2E)-but-2-enedioic acid; With dihydrogen peroxide; sodium tungstate; In sodium hydroxide; at 65 ℃; for 3h;

With sulfuric acid; barium(II) chloride; In diethyl ether; at 0 - 20 ℃; for 10h;

DOI:10.1002/hlca.200390015

Reference yield: 33.0%

dimethylfumarate (624-49-7) → (2S,3S)-Oxirane-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester (119163-08-5,119212-22-5) + DL-trans-epoxysuccinic acid (141-36-6,3272-11-5,16533-72-5,17015-08-6,17087-75-1,22734-83-4) + dimethyl trans-oxiranedicarboxylate (7403-10-3,56958-97-5,63119-87-9,66647-31-2,73889-79-9,85798-25-0)

Guidance literature:

With tert.-butylhydroperoxide; methyllithium; In tetrahydrofuran; hexane; benzene; at -78 - -20 ℃; for 1h;

DOI:10.1039/P19880002663

upstream raw materials:

benzene-1,2-diol

maleic acid

hydroquinone

p-benzoquinone

Downstream raw materials:

(2R,3S)-dimethyl oxirane-2,3-dicarboxylate

meso-epoxy-succinyl chloride

(-)-trans-2,3-oxiranedicarboxylic acid

(2R,3R)-oxirane-2,3-dicarboxylic acid

Refernces

• 1、 -. "EPOXY-CONTAINING POLY(ESTER AMIDES) AND METHODS OF USE". Page/Page column 45. . Retrieved 2010/11/30.
• 2、 Vyas, Shweta,Sharma, Pradeep K.. "Kinetics and mechanism of the oxidation of some unsaturated acids by quinolinium bromochromate". . p. 820 - 823. Retrieved 2007/10/03.