3,5-di-O-caffeoyl-muco-quinic acid

Base Information

• Chemical Name: 3,5-di-O-caffeoyl-muco-quinic acid
• CAS No.: 2450-53-5
• Molecular Formula: C₂₅H₂₄O₁₂
• Molecular Weight: 516.458
• Hs Code.: 29189900
• DSSTox Substance ID: DTXSID701031209
• Nikkaji Number: J1.899.072E,J2.819.930I,J1.377.724A
• Metabolomics Workbench ID: 67008
• Mol file: 2450-53-5.mol

Synonyms:3,5-di-O-caffeoyl-muco-quinic acid

Chemical Property of 3,5-di-O-caffeoyl-muco-quinic acid

Chemical Property:

• Appearance/Colour: Grey to yellow crystalline solid.
• Melting Point: 170-172oC
• Refractive Index: 1.719
• Boiling Point: 826.18 °C at 760 mmHg
• PKA: 3.54±0.50(Predicted)
• Flash Point: 280.356 °C
• PSA: 211.28000
• Density: 1.645 g/cm³
• LogP: 1.02960
• Storage Temp.: ?20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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:

99.5% ^*data from raw suppliers

IsochlorogenicAcidA ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

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
• Description: 3,5-Dicaffeoylquinic acid (3,5-DCQA) is a natural phenolic compound that has been found in L. japonica, I. kaushue, and other plants. It has antioxidant, anti-inflammatory, and antiviral biological activities. 3,5-DCQA scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell-free assay (IC50 = 71.8 μM) and inhibits superoxide production in human neutrophils activated by N-formyl-Met-Leu-Phe (fMLF) and cytochalasin B (IC50 = 1.92 μM). It inhibits HIV-1 integrase 3''-end processing, strand transfer, and disintegration in a cell-free assay (IC50s = 0.33, 0.34, and 0.66 μg/ml, respectively) and inhibits HIV-1-induced cytotoxicity in MT-2 cells (ED50 = 1 μg/ml). In vivo, 3,5-DCQA (25 mg/kg) protects mice from acute lung injury induced by LPS and decreases neutrophil count in bronchoalveolar lavage fluid (BALF).
• Uses: Isochlorogenic Acid A is a phenolic compound shown to provide protection against oxidative stress cells. DNA protective agent.

Technology Process of 3,5-di-O-caffeoyl-muco-quinic acid

There total 10 articles about 3,5-di-O-caffeoyl-muco-quinic 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: 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:

3-cyclohexylpropyl caffeate

methyl 3,4-dihydroxycinnamate

caffeic acid

D-(-)-quinic acid

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.