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

Suppliers and Price of 3,5-di-O-caffeoyl-muco-quinic acid

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
IsochlorogenicAcidA
50 mg
$ 390.00

Sigma-Aldrich
3,5-Di-caffeoylquinic acid ≥95% (LC/MS-ELSD)
1mg
$ 247.00

Sigma-Aldrich
3,5-Dicaffeoylquinic acid phyproof Reference Substance
10mg
$ 393.00

Medical Isotopes, Inc.
IsochlorogenicAcidA
50 mg
$ 2200.00

JR MediChem
Isochlorogenic?acid?A(NewProduct) 98%
20mg
$ 108.00

DC Chemicals
IsochlorogenicacidA >98%,StandardReferencesGrade
100 mg
$ 550.00

DC Chemicals
IsochlorogenicacidA >98%,StandardReferencesGrade
1 g
$ 1800.00

DC Chemicals
IsochlorogenicacidA >98%,StandardReferencesGrade
250 mg
$ 950.00

Crysdot
3,5-Di-O-caffeoylquinicacid 98+%
100mg
$ 697.00

Crysdot
3,5-Di-O-caffeoylquinicacid 98+%
50mg
$ 389.00

Total 80 raw suppliers

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:

≥98% ^*data from raw suppliers

IsochlorogenicAcidA ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:
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%

: 1352319-04-0
3,3'-(((1R,2S,3R,5S)-5-carboxy-2,5-dihydroxycyclohexane-1,3-diyl)bis(oxy))bis(3-oxopropanoic acid)

: 139-85-5
3,4-dihydroxybenzaldehyde

: 2450-53-5,16758-05-7,89919-61-9,89919-62-0,101222-97-3
3,5-di-O-caffeoylquinic acid

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:

: 1049703-62-9
chlorogenic acid

: 331-39-5,501-16-6
caffeic 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
1,3,4,5-tetrahydroxy-cyclohexanecarboxylic acid

: 2450-53-5,16758-05-7,89919-61-9,89919-62-0,101222-97-3
3,5-dicaffeoylquinic acid

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

Reference yield:

: 1352319-06-2
(1R,3R,4S,5R)-benzyl 1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohexanecarboxylate

: 2450-53-5,16758-05-7,89919-61-9,89919-62-0,101222-97-3
3,5-di-O-caffeoylquinic acid

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