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3,5-Di-O-caffeoylquinic acid methyl ester

CAS# 159934-13-1

3,5-Di-O-caffeoylquinic acid methyl ester

Catalog No. BCN6491----Order now to get a substantial discount!

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3,5-Di-O-caffeoylquinic acid methyl ester: 5mg $828 In Stock
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Quality Control of 3,5-Di-O-caffeoylquinic acid methyl ester

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Chemical structure

3,5-Di-O-caffeoylquinic acid methyl ester

3D structure

Chemical Properties of 3,5-Di-O-caffeoylquinic acid methyl ester

Cas No. 159934-13-1 SDF Download SDF
PubChem ID 10075681 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 (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylate
SMILES COC(=O)C1(CC(C(C(C1)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O
Standard InChIKey VEBNYMXKXIIGFX-IYVYCCGLSA-N
Standard InChI InChI=1S/C26H26O12/c1-36-25(34)26(35)12-20(37-22(31)8-4-14-2-6-16(27)18(29)10-14)24(33)21(13-26)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h2-11,20-21,24,27-30,33,35H,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 3,5-Di-O-caffeoylquinic acid methyl ester

The flowerbud of Lonicera japonica Thunb.

Biological Activity of 3,5-Di-O-caffeoylquinic acid methyl ester

Description3,5-Di-O-caffeoylquinic acid methyl ester exhibits potent inhibitory activities against the formation of advanced glycation end products (AGEs); it exhibits cytotoxicity actions against human cervix carcinoma HeLa cells. 3,5-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.

Constituents of the flowers of Erigeron annuus with inhibitory activity on the formation of advanced glycation end products (AGEs) and aldose reductase.[Pubmed: 18704333 ]

Arch Pharm Res. 2008 Jul;31(7):900-4.


METHODS AND RESULTS:
Seven phenolic compounds, caffeic acid (1), 4-hydroxybenzoic acid (2), 4-methoxybenzoic acid (3), protocatechuic acid (4), eugenol O-beta-D: -glucopyranoside (5), 3,6-di-O-feruloylsucrose (6), and 3,5-Di-O-caffeoylquinic acid methyl ester (7), were isolated from an EtOAc-soluble partition of the flowers of Erigeron annuus. The structures of 1-7 were determined by spectroscopic data interpretation, particularly 1D and 2D NMR studies, and by comparison of their data with those published in the literature. All the isolates were subjected to in vitro bioassays to evaluate their inhibitory activities against the formation of advanced glycation end products (AGEs) and rat lens aldose reductase (RLAR).
CONCLUSIONS:
Of the compounds, 1, 6, and 7 exhibited potent inhibitory activities against the formation of AGEs. In the RLAR assay, compound 7 showed the most potent inhibitory activity.

Protocol of 3,5-Di-O-caffeoylquinic acid methyl ester

Cell Research

Functional analyses on antioxidant, anti-inflammatory, and antiproliferative effects of extracts and compounds from Ilex latifolia Thunb., a Chinese bitter tea.[Pubmed: 25118953 ]

J Agric Food Chem. 2014 Aug 27;62(34):8608-15.

Ilex latifolia Thunb., widely distributed in China, has been used as a functional food and drunk for a long time.
METHODS AND RESULTS:
This study was aimed to identify the bioactive constituents with antioxidant, antitumor, and anti-inflammatory properties. I. latifolia was extracted with 95% ethanol and then partitioned into four fractions: petroleum ether fraction, ethyl acetate fraction, n-butanol fraction, and water fraction. Results showed that the ethyl acetate fraction was found to have significant ferric reducing antioxidant power activity, DPPH radical scavenging activity, and oxygen radical absorbance capacity, cytotoxicity against human cervix carcinoma HeLa cells, and inhibitory effect on NO production in macrophage RAW 264.7 cells. Five compounds were isolated from the ethyl acetate fraction, and they were identified as ethyl caffeate (1), ursolic acid (2), chlorogenic acid (3), 3,4-di-O-caffeoylquinic acid methyl ester (4), and 3,5-Di-O-caffeoylquinic acid methyl ester (5), the last two of which were isolated for the first time from I. latifolia. Compounds 4 and 5 exhibited cytotoxicity actions against tumor cell line. Compound 3 showed the strongest anti-inflammatory activity of all the compounds.
CONCLUSIONS:
The results obtained in this work might contribute to the understanding of biological activities of I. latifolia and further investigation on its potential application values for food and drug.

3,5-Di-O-caffeoylquinic acid methyl ester Dilution Calculator

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3,5-Di-O-caffeoylquinic acid methyl ester Molarity Calculator

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Preparing Stock Solutions of 3,5-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 3,5-Di-O-caffeoylquinic acid methyl ester

Constituents of the flowers of Erigeron annuus with inhibitory activity on the formation of advanced glycation end products (AGEs) and aldose reductase.[Pubmed:18704333]

Arch Pharm Res. 2008 Jul;31(7):900-4.

Seven phenolic compounds, caffeic acid (1), 4-hydroxybenzoic acid (2), 4-methoxybenzoic acid (3), protocatechuic acid (4), eugenol O-beta-D: -glucopyranoside (5), 3,6-di-O-feruloylsucrose (6), and 3,5-Di-O-caffeoylquinic acid methyl ester (7), were isolated from an EtOAc-soluble partition of the flowers of Erigeron annuus. The structures of 1-7 were determined by spectroscopic data interpretation, particularly 1D and 2D NMR studies, and by comparison of their data with those published in the literature. All the isolates were subjected to in vitro bioassays to evaluate their inhibitory activities against the formation of advanced glycation end products (AGEs) and rat lens aldose reductase (RLAR). Of the compounds, 1, 6, and 7 exhibited potent inhibitory activities against the formation of AGEs. In the RLAR assay, compound 7 showed the most potent inhibitory activity.

Functional analyses on antioxidant, anti-inflammatory, and antiproliferative effects of extracts and compounds from Ilex latifolia Thunb., a Chinese bitter tea.[Pubmed:25118953]

J Agric Food Chem. 2014 Aug 27;62(34):8608-15.

Ilex latifolia Thunb., widely distributed in China, has been used as a functional food and drunk for a long time. This study was aimed to identify the bioactive constituents with antioxidant, antitumor, and anti-inflammatory properties. I. latifolia was extracted with 95% ethanol and then partitioned into four fractions: petroleum ether fraction, ethyl acetate fraction, n-butanol fraction, and water fraction. Results showed that the ethyl acetate fraction was found to have significant ferric reducing antioxidant power activity, DPPH radical scavenging activity, and oxygen radical absorbance capacity, cytotoxicity against human cervix carcinoma HeLa cells, and inhibitory effect on NO production in macrophage RAW 264.7 cells. Five compounds were isolated from the ethyl acetate fraction, and they were identified as ethyl caffeate (1), ursolic acid (2), chlorogenic acid (3), 3,4-di-O-caffeoylquinic acid methyl ester (4), and 3,5-Di-O-caffeoylquinic acid methyl ester (5), the last two of which were isolated for the first time from I. latifolia. Compounds 4 and 5 exhibited cytotoxicity actions against tumor cell line. Compound 3 showed the strongest anti-inflammatory activity of all the compounds. The results obtained in this work might contribute to the understanding of biological activities of I. latifolia and further investigation on its potential application values for food and drug.

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