(2S,1R)-1,2-Bis(3-(3,4-dihydroxyphenyl)prop-2-enoyloxy)ethane-1,2-dicarboxylic acid

Base Information

• Chemical Name: (2S,1R)-1,2-Bis(3-(3,4-dihydroxyphenyl)prop-2-enoyloxy)ethane-1,2-dicarboxylic acid
• CAS No.: 133520-29-3
• Molecular Formula: C22H18O12
• Molecular Weight: 474.378
• Nikkaji Number: J503.501E,J970.045E
• Wikidata: Q105346687
• Metabolomics Workbench ID: 133478
• ChEMBL ID: CHEMBL397730
• Mol file: 133520-29-3.mol

Synonyms:meso-DCTA;Chicoric acid, meso form;Dicaffeoyltartaric acid, meso form;CHEMBL397730;133520-29-3;(2S,1R)-1,2-Bis(3-(3,4-dihydroxyphenyl)prop-2-enoyloxy)ethane-1,2-dicarboxylic acid;Butanedioic acid, 2,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (R*,S*-(E,E))-;(2S,1R)-1,2-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]ethane-1,2-dicarboxylic acid;Butanedioic acid, 2,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, [R*,S*-(E,E)]-;SCHEMBL21176639;BDBM50476592;AKOS015902617;(2R,3S)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid;2-O,3-O-Bis[3-(3,4-dihydroxyphenyl)propenoyl]-meso-tartaric acid;(2R,3S)-2,3-Bis[[(E)-3-(3,4-dihydroxyphenyl)propenoyl]oxy]butanedioic acid

Chemical Property of (2S,1R)-1,2-Bis(3-(3,4-dihydroxyphenyl)prop-2-enoyloxy)ethane-1,2-dicarboxylic acid

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 11
• Exact Mass: 474.07982601
• Heavy Atom Count: 34
• Complexity: 740

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)OC(C(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)C(=O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1/C=C/C(=O)O[C@@H](C(=O)O)[C@H](OC(=O)/C=C/C2=CC(=C(C=C2)O)O)C(=O)O)O)O

Technology Process of (2S,1R)-1,2-Bis(3-(3,4-dihydroxyphenyl)prop-2-enoyloxy)ethane-1,2-dicarboxylic acid

There total 20 articles about (2S,1R)-1,2-Bis(3-(3,4-dihydroxyphenyl)prop-2-enoyloxy)ethane-1,2-dicarboxylic 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: 92.0%

dibenzyl (-)-(2R,3R)-2,3-bis{3-[2,3-bis(3,4-dibenzyloxy)phenyl]prop-2-enoyloxy}-L-tartrate (488148-82-9) → (-)-chicoric acid (6537-80-0,52248-48-3,53797-30-1,70831-56-0,133520-29-3)

Guidance literature:

With triethylsilane; palladium diacetate; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1002/1522-2675(200208)85:8<2328::AID-HLCA2328>3.0.CO;2-X

Reference yield: 90.0%

(2R,3R)-2,3-Bis-[(E)-3-(3,4-diacetoxy-phenyl)-acryloyloxy]-succinic acid → (-)-chicoric acid (6537-80-0,52248-48-3,53797-30-1,70831-56-0,133520-29-3)

Guidance literature:

With hydrogenchloride; In acetone; for 3h; Heating;

DOI:10.1080/00397919808005946

Reference yield: 66.0%

dibenzyl (+)-(2S,3S)-2,3-bis{3-[3,4-bis(benzyloxy)phenyl]prop-2-enoyloxy}-D-tartrate (488148-83-0) → caftaric acid (6537-80-0,53797-30-1,70831-56-0,133520-29-3,52248-48-3)

Guidance literature:

With triethylsilane; palladium diacetate; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1002/1522-2675(200208)85:8<2328::AID-HLCA2328>3.0.CO;2-X

upstream raw materials:

D-tartaric acid

dibenzyl (+)-(2S,3S)-2,3-bis{3-[3,4-bis(benzyloxy)phenyl]prop-2-enoyloxy}-D-tartrate

caffeic acid

ethyl caffeate

Downstream raw materials:

cis-chicoric acid

Refernces

• 1、 Lamidey, Anne-Marie,Fernon, Lionel,Pouysegu, Laurent,Delattre, Charlotte,Quideau, Stephane,Pardon, Patrick. "A convenient synthesis of the Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (-)-(2R,3R)-chicoric acid". . p. 2328 - 2334. Retrieved 2007/10/03.