(2R,3R)-2,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid

Base Information

• Chemical Name: (2R,3R)-2,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid
• CAS No.: 6537-80-0
• Molecular Formula: C₂₂H₁₈O₁₂
• Molecular Weight: 474.378
• Hs Code.: 29182900
• DSSTox Substance ID: DTXSID90110066
• Mol file: 6537-80-0.mol

Synonyms:dl-Chicoric acid;(2R,3R)-2,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid;(-)-Chicoric acid;trans-Caffeoyltartaric acid;SCHEMBL964775;DTXSID90110066;AKOS030228562;FT-0645068;D78144

Chemical Property of (2R,3R)-2,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid

Chemical Property:

• Vapor Pressure: 5.86E-26mmHg at 25°C
• Melting Point: 200～208℃
• Refractive Index: 1.726
• Boiling Point: 785 °C at 760 mmHg
• PKA: 1.47±0.25(Predicted)
• Flash Point: 272.9 °C
• PSA: 208.12000
• Density: 1.641g/cm³
• LogP: 1.22840
• Storage Temp.: ?20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly)
• 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:

Natural extract,4% Polyphenols , ^*data from raw suppliers

Chicoric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-42/43
• Safety Statements: 22-36/37-45

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=C1C=CC(=O)O[C@H]([C@H](C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)C(=O)O)O)O
• Uses: Chicoric Acid is an effective inhibitor of human immunodeficiency virus type-1 (HIV-1) integrase and the replication in tissues. Also a class of cannabinomimetics with CB2 receptor-dependent and indep endent Chicoric Acid is an effective inhibitor of human immunodeficiency virus type-1 (HIV-1) integrase and the replication in tissues. Also a class of cannabinomimetics with CB2 receptor-dependent and independent

Technology Process of (2R,3R)-2,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid

There total 19 articles about (2R,3R)-2,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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、 Zhao, He,Burke Jr., Terrence R.. "Facile syntheses of (2R,3R)-(-)- and (2S,3S)-(+)-chicoric acids". . p. 737 - 740. Retrieved 2007/10/03.