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4,5-Di-O-caffeoylquinic acid methyl ester

CAS# 188742-80-5

4,5-Di-O-caffeoylquinic acid methyl ester

2D Structure

Catalog No. BCN6492----Order now to get a substantial discount!

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4,5-Di-O-caffeoylquinic acid methyl ester

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Chemical Properties of 4,5-Di-O-caffeoylquinic acid methyl ester

Cas No. 188742-80-5 SDF Download SDF
PubChem ID 10052718 Appearance Powder
Formula C26H26O12 M.Wt 530.5
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name methyl (1R,3R,4S,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylate
SMILES COC(=O)C1(CC(C(C(C1)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O)O
Standard InChIKey PKJBSZTYNDRXEQ-GMGOHGFSSA-N
Standard InChI InChI=1S/C26H26O12/c1-36-25(34)26(35)12-20(31)24(38-23(33)9-5-15-3-7-17(28)19(30)11-15)21(13-26)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h2-11,20-21,24,27-31,35H,12-13H2,1H3/b8-4+,9-5+/t20-,21-,24+,26-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 4,5-Di-O-caffeoylquinic acid methyl ester

The flowerbud of Lonicera japonica Thunb.

Biological Activity of 4,5-Di-O-caffeoylquinic acid methyl ester

Description4,5-Di-O-caffeoylquinic acid methyl ester shows high efficiency and low toxicity with antivirus activity against RSV.
TargetsHSV
In vitro

Study on chemical constituents from Re-Du-Ning Injection (II).[Reference: WebLink]

Chinese Traditional & Herbal Drugs, 2015 , 46 (11) :1597-602.

To investigate the chemical constituents from Re-Du-Ning Injection (RDN).
METHODS AND RESULTS:
The chemical constituents were isolated by chromatography on silica gel, ODS, Sephadex LH-20, and Toyopearl HW-40 columns and reverse phase MPLC and HPLC repeatedly. Their structures were identified by spectral data and physicochemical property. Sixteen compounds were isolated and identified as 5-O-caffeoylquinic acid (1), 5-O-caffeoylquinic acid methyl ester (2), 4-O-caffeoylquinic acid (3), 5-O-caffeoylquinic acid methyl ester (4), 4,5-di-O-caffeoylquinic acid (5), 4,5-Di-O-caffeoylquinic acid methyl ester (6), 3,5- di-O-caffeoylquinic acid (7), 3,5-di-O-caffeoylquinic acid methyl ester (8), 3,4-di-O-caffeoylquinic acid (9), 3,4-di-O-caffeoylquinic acid methyl ester (10), secologanic acid (11), vogeloside (12), 7-epi-vogeloside (13), E-aldosecologanin (14), Z-aldosecologanin (15), and 5H,8H-pyrano[4,3-d] thiazolo[3,2-a] pyridine-3-carboxylic acid (16). Compounds 1-10 showed high efficiency and low toxicity with antivirus activity against RSV.
CONCLUSIONS:
All the isolated compounds are reported from RDN Injection for the first time, and caffeoylquinic acids may be one of antivirus pharmacodynamic material bases of RDN.

4,5-Di-O-caffeoylquinic acid methyl ester Dilution Calculator

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4,5-Di-O-caffeoylquinic acid methyl ester Molarity Calculator

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Preparing Stock Solutions of 4,5-Di-O-caffeoylquinic acid methyl ester

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.885 mL 9.4251 mL 18.8501 mL 37.7003 mL 47.1254 mL
5 mM 0.377 mL 1.885 mL 3.77 mL 7.5401 mL 9.4251 mL
10 mM 0.1885 mL 0.9425 mL 1.885 mL 3.77 mL 4.7125 mL
50 mM 0.0377 mL 0.1885 mL 0.377 mL 0.754 mL 0.9425 mL
100 mM 0.0189 mL 0.0943 mL 0.1885 mL 0.377 mL 0.4713 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 4,5-Di-O-caffeoylquinic acid methyl ester

Identification of alpha-glucosidase inhibitors from the leaves of Pluchea indica (L.) Less., a traditional Indonesian herb: promotion of natural product use.[Pubmed:24697406]

Nat Prod Res. 2014;28(17):1350-3.

A promising approach for treating diabetes mellitus (DM) is to decrease postprandial hyperglycaemia by suppressing carbohydrate digestion using alpha-glucosidase inhibitors. Pluchea indica leaf extracts possess inhibitory activity against intestinal maltase. Enzyme assay-guided fractionation by chromatography yielded five active caffeoylquinic acid derivatives (1-5). Their structures were elucidated by mass spectrometry and NMR analysis and completed by comparison with reference data. 3,5-Di-O-caffeoylquinic acid (1), 4,5-Di-O-caffeoylquinic acid methyl ester (2), 3,4,5-tri-O-caffeoylquinic acid methyl ester (3), 3,4,5-tri-O-caffeoylquinic acid (4) and 1,3,4,5-tetra-O-caffeoylquinic acid (5) were isolated. Comparison of the activities of each isolate suggested that both methyl esterification of quinic acid and the number of caffeate groups in the molecule were important for the inhibitory activity. This study provides basic information for further examination of the suitability of P. indica as a functional food and medicinal supplement for the treatment and prevention of diabetes.

[Aromatic constituents of Heteroplexis micocephal and their bioactivities].[Pubmed:21473152]

Zhongguo Zhong Yao Za Zhi. 2011 Jan;36(1):48-56.

OBJECTIVE: To investigate the chemical constituents of Heteroplexis micocephal and their bioactivities. METHOD: The constituents were isolated by using a combination of various chromatographic techniques including column chromatography over macroporous adsorbent resin, silica gel, Pharmadex LH-20, and C-18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic data analysis. In vitro cytotoxic, HIV-1 replication, neuroprotective, and anti-inflammatory activities were screened by using cell-based models. RESULT: Thirty-one compounds were obtained. Twelve of them are phenylpropanols, and the structures were elucidated as (+)-(7S,8R)-guaiacylglycerol (1), ferulic acid (2), cinnamate methyl ester (3), 1-eicosanyl 3,4-dihydroxycinnamate (4), morinin B (5), sinapyl diangelate (6), chlorogenic acid (7), 4-O-caffeoylquinic acid (8), 5-O-caffeoylquinic acid (9), 5-O-caffeoylquinic acid methyl ester (10), 1,5-di-O-caffeoylquinic acid (11) and 4,5-Di-O-caffeoylquinic acid methyl ester (12). Three lignans, (+)-pinoresinol (13), prinsepiol (14) and (+)-pinoresinol-O-beta-D-glucopyranoside (15). Four acetophenones, 2,4-diacetylanisole (16), espeleton (17), viscidone (18) and 12-hydroxytremetone-12-O-beta-D-glucopyranoside (19). Nine flavones, isosakuranetin (20), hesperetin (21), 3-methoxy-5,7,3',4'-tetrahydroxyflavone (22), acacetin (23), 5-hydroxy-7,4'- dimethoxyflavone (24), 7-methoxy-4',5, 6-trihydroxyflavone (25), 3,3'-dimethylquercetin (26), kaempferol 3-O-rutinoside (27), rutin (28). And three coumarins scopoletin (29), umbelliferone (30) and ayapin (31). Compound 6 and 22 showed selective cytotoxicities against a human stomach cancer cell line(BGC-823) and a human lung cancer cell line (A549) with IC50 values of 3.74 x 10(-5) and 7.17 x 10(-5) mol L(-1), respectively. In addition, Compound 6 showed a potent activity inhibiting HIV-1 replication with an IC50 value of 4.04 x 10(-6) mol L(-1), while 22 showed neuroprotective activity Against the MPP+ induced PC12-syn cell damage, with a relative protection ratio of 105.2% (P < 0.01) at a concentration of 10(-5) mol L(-1). Compound 26 and 31 showed inhibitory activities against the release of beta-glucuronidase of the polymorphous nuclear leukocytes induced by platelet activating factor (PAF), with inhibitory rates of 75.6% (P < 0.001) and 53. 9% (P < 0.01), respectively. CONCLUSION: Compounds 1-31 were obtained from the genus Heteroplexis for the first time. Compound 6 and 22 possessed selective cytotoxicities against human cancer cell lines BGC-823 and A549, respectively. In addition, Compound 6 showed a potent activity inhibiting HIV-1 replication while 22 showed neuroprotective activity against the MPP+ induced PC12-syn cell damage. Compound 26 and 31 were potent anti-inflammatory agents.

Phagnalon rupestre as a source of compounds active on contact hypersensitivity.[Pubmed:12094308]

Planta Med. 2002 Jun;68(6):561-4.

The effect of Phagnalon rupestre MeOH extract on dinitrofluorobenzene- and sheep red blood cells-induced hypersensitivity was investigated. Eight compounds were identified: three dimethylallyl-hydroquinone glucosides (1 - 3), 3,5- and 4,5-Di-O-caffeoylquinic acid methyl esters (4 and 5), their free carboxyl analogues (6 and 7), and luteolin 7-O-beta-glucoside (8). All were tested for dinitrofluorobenzene-induced contact hypersensitivity inhibitory activity. Flavonoid 8 was the most active (49 % and 79 % inhibition at 24 and 96 h, respectively). The hydroquinones 1, 2 and 3 were effective at 96 h after challenge (62 %, 73 % and 60 % inhibition, respectively), while some of the dicaffeoylquinic derivatives (4 and 7) produced slightly lower reduction of the inflammatory reaction.

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