Isochlorogenic acid A

Base Information

• Chemical Name: Isochlorogenic acid A
• CAS No.: 89919-62-0
• Molecular Formula: C₂₅H₂₄O₁₂
• Molecular Weight: 516.458
• European Community (EC) Number: 815-082-0,845-638-8
• UNII: ND94C5E75K
• DSSTox Substance ID: DTXSID00424282
• Nikkaji Number: J441.723B,J3.381.958G,J749.366E,J2.301.841A,J1.453.981F
• Wikidata: Q72465349,Q27134233,Q105145299
• Pharos Ligand ID: T6J3KCTDCK3T
• Metabolomics Workbench ID: 64116,143802
• ChEMBL ID: CHEMBL249447,CHEMBL4289566,CHEMBL4466054
• Mol file: 89919-62-0.mol

Synonyms:(3R,5R)-3,5-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl))-1,4-dihydroxy-cyclohexanecarboxylic acid;3,5-DCQA;3,5-di-O-caffeoylquinic acid;3,5-dicaffeoylquinic acid;3,5-H56:H75dicaffeoyl-epi-quinic acid;3,5-O-dicaffeoylquinic acid;CJ 4-16-4;CJ-4-16-4;isochlorogenic acid A

Chemical Property of Isochlorogenic acid A

Chemical Property:

• Boiling Point: 826.2±65.0 °C(Predicted)
• PKA: 3.52±0.50(Predicted)
• PSA: 211.28000
• Density: 1.64
• LogP: 1.02960
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 9
• Exact Mass: 516.12677620
• Heavy Atom Count: 37
• Complexity: 825

Purity/Quality:

99% ^*data from raw suppliers

3,5-Dicaffeoylquinic acid 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O
• Isomeric SMILES: C1C(C[C@H](C([C@@H]1OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)(O)C(=O)O

Technology Process of Isochlorogenic acid A

There total 10 articles about Isochlorogenic acid A 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: 68.0%

3,3'-(((1R,2S,3R,5S)-5-carboxy-2,5-dihydroxycyclohexane-1,3-diyl)bis(oxy))bis(3-oxopropanoic acid) (1352319-04-0) + 3,4-dihydroxybenzaldehyde (139-85-5) → 3,5-di-O-caffeoylquinic acid (2450-53-5,16758-05-7,89919-61-9,89919-62-0,101222-97-3)

Guidance literature:

With piperidine; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 192h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.10.127

Reference yield:

chlorogenic acid (1049703-62-9) → caffeic acid (331-39-5,501-16-6) + 1,3,4,5-tetrahydroxy-cyclohexanecarboxylic acid (77-95-2,1010-25-9,7216-27-5,23804-29-7,23804-41-3,23804-44-6,36413-60-2,135558-83-7,135558-85-9,470-63-3,562-73-2,23804-34-4,23804-38-8) + 3,5-dicaffeoylquinic acid (2450-53-5,16758-05-7,89919-61-9,89919-62-0,101222-97-3)

Guidance literature:

at 30 ℃; for 0.5h; pH 6.4; enzyme from Ipomoea batatas;

Reference yield:

(1R,3R,4S,5R)-benzyl 1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohexanecarboxylate (1352319-06-2) → 3,5-di-O-caffeoylquinic acid (2450-53-5,16758-05-7,89919-61-9,89919-62-0,101222-97-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine hydrofluoride / tetrahydrofuran / 12 h / 0 - 20 °C

2: toluene / 5 h / 60 °C / Inert atmosphere

3: 10% Pd(OH)₂ on C; hydrogen / methanol / 36 h / 20 °C

4: piperidine; dmap / N,N-dimethyl-formamide / 192 h / 20 °C / Inert atmosphere

With piperidine; dmap; pyridine hydrofluoride; 10% Pd(OH)₂ on C; hydrogen; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 4: Knoevenagel condensation;

DOI:10.1016/j.tetlet.2011.10.127

upstream raw materials:

(1R,3R,4S,5R)-benzyl 1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohexanecarboxylate

C₂₇H₃₈O₆Si

(1S,3R,4S,5R)-benzyl 1,4-bis(benzyloxy)-3,5-dihydroxycyclohexanecarboxylate

3,3'-(((1R,2S,3R,5S)-2,5-bis(benzyloxy)-5-((benzyloxy)carbonyl)cyclohexane-1,3-diyl)bis(oxy))bis(3-oxopropanoic acid)

Downstream raw materials:

caffeic acid

D-(-)-quinic acid

3-cyclohexylpropyl caffeate

methyl 3,4-dihydroxycinnamate

Refernces

• 1、 Kojima, Mineo,Kondo, Tadao. "An Enzyme in Sweet Potato Root which Catalyzes the Conversion of Chlorogenic Acid, 3-Caffeoylquininc Acid to Isochlorogenic Acid, 3,5-Dicaffeoylquinic Acid". . p. 2467 - 2470. Retrieved 2007/10/02.