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1-Caffeoylquinic acid

CAS# 1241-87-8

1-Caffeoylquinic acid

Catalog No. BCN5911----Order now to get a substantial discount!

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Quality Control of 1-Caffeoylquinic acid

Number of papers citing our products

Chemical structure

1-Caffeoylquinic acid

3D structure

Chemical Properties of 1-Caffeoylquinic acid

Cas No. 1241-87-8 SDF Download SDF
PubChem ID 6451212 Appearance White powder
Formula C16H18O9 M.Wt 354.31
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4,5-trihydroxycyclohexane-1-carboxylic acid
SMILES C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O)O
Standard InChIKey GWTUHAXUUFROTF-DUXPYHPUSA-N
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 1-Caffeoylquinic acid

The herb of Lonicera japonica Thunb.

Biological Activity of 1-Caffeoylquinic acid

Description1-Caffeoylquinic acid is an important intermediate in lignin biosynthesis. 1-Caffeoylquinic acid has anti-influenza, and antioxidant activities, it also slows the release of glucose into the bloodstream after a meal.
TargetsNF-kB
In vitro

Qualitative and quantitative analysis of phenolics in Tetrastigma hemsleyanum and their antioxidant and antiproliferative activities.[Pubmed: 24151872]

J Agric Food Chem. 2013 Nov 6;61(44):10507-15.

The phenolic profiles of Tetrastigma hemsleyanum leaf extracts by different solvents (80% methanol, ethyl acetate and hexane) and their antioxidant and antiproliferative activities were investigated.
METHODS AND RESULTS:
Thirteen phenolic compounds (3-caffeoylquinic acid, 5-caffeoylquinic acid, 1-Caffeoylquinic acid, 5-p-coumaroylquinic acid, isoorientin-2″-O-rhamnoside, isoorientin, orientin-2″-O-rhamnoside, orientin, 1-p-coumaroylquinic acid, vitexin-2″-O-rhamnoside, isovitexin-2″-O-rhamnoside, vitexin and isovitexin) were identified in T. hemsleyanum leaves for the first time, and six of them were quantified using a combination of LC-QTOF-MS and LC-QqQ-MS techniques. It was found that 80% methanol extract exhibited the highest antioxidant activities.
CONCLUSIONS:
This paper provides a complete picture of phenolics in T. hemsleyanum leaves and relates them to their antioxidant and antiproliferative activities.

Protocol of 1-Caffeoylquinic acid

Kinase Assay

Dietary phytochemicals as potent chemotherapeutic agents against breast cancer: Inhibition of NF-κB pathway via molecular interactions in rel homology domain of its precursor protein p105.[Pubmed: 23661994]

Pharmacogn Mag. 2013 Jan;9(33):51-7.

Dietary phytochemicals consist of a wide variety of biologically active compounds that are ubiquitous in plants, many of which have been reported to have anti-tumor as well as anti-inflammatory properties. In the present study, we aimed to validate these findings by using docking protocols and explicate the possible mechanism of action for a dataset of nine phytochemicals namely boswellic acid, 1-Caffeoylquinic acid, ellagic acid, emodin, genistein, guggulsterone, quercetin, resveratrol, and sylibinin from different plants against the nuclear factor- kappaB (NF-κB) precursor protein p105, an important transcription factor reported to be overexpressed in breast cancer.
METHODS AND RESULTS:
2-D structures of all phytochemicals were retrieved from PubChem Compound database and their subsequent conversion into 3-D structures was performed by using online software system CORINA. The X-ray crystallographic structure of the NF-κB precursor p105 was extracted from Brookhaven Protein Data Bank. Molecular docking simulation study was carried out by using AutoDock Tools 4.0. Our results showed significant binding affinity of different phytochemicals with the Rel homology domain of the NF-κB precursor protein p105. Quercetin and 1-Caffeoylquinic acid were found to be very effective inhibitors against target molecule as they showed binding energy of -12.11 and -11.50 Kcal/mol, respectively. The order of affinity of other ligands with p105 was found as follows: guggulsterone > sylibinin > emodin > resveratrol > genistein > boswellic acid > ellagic acid.
CONCLUSIONS:
Our in silico study has explored the possible chemopreventive mechanism of these phytochemicals against the NF-κB precursor protein p105 and deciphered that quercetin, 1-Caffeoylquinic acid and guggulsterone were the potent inhibitors against target molecule. In addition, large scale preclinical and clinical trials are needed to explore the role of these chemotherapeutic molecules against the NF-κB precursor protein p105 in cure and prevention of breast cancer.

1-Caffeoylquinic acid Dilution Calculator

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1-Caffeoylquinic acid Molarity Calculator

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Preparing Stock Solutions of 1-Caffeoylquinic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8224 mL 14.1119 mL 28.2239 mL 56.4477 mL 70.5597 mL
5 mM 0.5645 mL 2.8224 mL 5.6448 mL 11.2895 mL 14.1119 mL
10 mM 0.2822 mL 1.4112 mL 2.8224 mL 5.6448 mL 7.056 mL
50 mM 0.0564 mL 0.2822 mL 0.5645 mL 1.129 mL 1.4112 mL
100 mM 0.0282 mL 0.1411 mL 0.2822 mL 0.5645 mL 0.7056 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 1-Caffeoylquinic acid

Dietary phytochemicals as potent chemotherapeutic agents against breast cancer: Inhibition of NF-kappaB pathway via molecular interactions in rel homology domain of its precursor protein p105.[Pubmed:23661994]

Pharmacogn Mag. 2013 Jan;9(33):51-7.

BACKGROUND: Dietary phytochemicals consist of a wide variety of biologically active compounds that are ubiquitous in plants, many of which have been reported to have anti-tumor as well as anti-inflammatory properties. OBJECTIVE: In the present study, we aimed to validate these findings by using docking protocols and explicate the possible mechanism of action for a dataset of nine phytochemicals namely boswellic acid, 1-Caffeoylquinic acid, ellagic acid, emodin, genistein, guggulsterone, quercetin, resveratrol, and sylibinin from different plants against the nuclear factor- kappaB (NF-kappaB) precursor protein p105, an important transcription factor reported to be overexpressed in breast cancer. MATERIALS AND METHODS: 2-D structures of all phytochemicals were retrieved from PubChem Compound database and their subsequent conversion into 3-D structures was performed by using online software system CORINA. The X-ray crystallographic structure of the NF-kappaB precursor p105 was extracted from Brookhaven Protein Data Bank. Molecular docking simulation study was carried out by using AutoDock Tools 4.0. RESULTS: Our results showed significant binding affinity of different phytochemicals with the Rel homology domain of the NF-kappaB precursor protein p105. Quercetin and 1-Caffeoylquinic acid were found to be very effective inhibitors against target molecule as they showed binding energy of -12.11 and -11.50 Kcal/mol, respectively. The order of affinity of other ligands with p105 was found as follows: guggulsterone > sylibinin > emodin > resveratrol > genistein > boswellic acid > ellagic acid. CONCLUSION: Our in silico study has explored the possible chemopreventive mechanism of these phytochemicals against the NF-kappaB precursor protein p105 and deciphered that quercetin, 1-Caffeoylquinic acid and guggulsterone were the potent inhibitors against target molecule. In addition, large scale preclinical and clinical trials are needed to explore the role of these chemotherapeutic molecules against the NF-kappaB precursor protein p105 in cure and prevention of breast cancer.

Qualitative and quantitative analysis of phenolics in Tetrastigma hemsleyanum and their antioxidant and antiproliferative activities.[Pubmed:24151872]

J Agric Food Chem. 2013 Nov 6;61(44):10507-15.

The phenolic profiles of Tetrastigma hemsleyanum leaf extracts by different solvents (80% methanol, ethyl acetate and hexane) and their antioxidant and antiproliferative activities were investigated. Thirteen phenolic compounds (3-caffeoylquinic acid, 5-caffeoylquinic acid, 1-Caffeoylquinic acid, 5-p-coumaroylquinic acid, isoorientin-2''-O-rhamnoside, isoorientin, orientin-2''-O-rhamnoside, orientin, 1-p-coumaroylquinic acid, vitexin-2''-O-rhamnoside, isovitexin-2''-O-rhamnoside, vitexin and isovitexin) were identified in T. hemsleyanum leaves for the first time, and six of them were quantified using a combination of LC-QTOF-MS and LC-QqQ-MS techniques. It was found that 80% methanol extract exhibited the highest antioxidant activities (DPPH, 3.32 mmol of Trolox/g DW; ABTS, 1.38 mmol of Trolox/g DW; FRAP, 1.85 mmol of FeSO4/g DW), while the hexane extract had the lowest (1.23, 0.43 and 0.13, respectively). Total phenolic contents (TPC) of various extracts of T. hemsleyanum leaves ranged from 28.95 to 275.71 mg of GAE/g DW. Also, total antioxidant activities as evaluated by ABTS, FRAP and DPPH assays were correlated well with TPC. In addition, 80% methanol extract provided antiproliferative activity on HepG2 cells (IC50 = 524 mug/mL). This paper provides a complete picture of phenolics in T. hemsleyanum leaves and relates them to their antioxidant and antiproliferative activities.

Description

1-Caffeoylquinic acid is an effective NF-κB inhibitor, shows significant binding affinity to the RH domain of p105 with Ki of 0.002 μM and binding energy of 1.50 Kcal/mol. 1-Caffeoylquinic acid has anti-oxidative stress ability. 1-Caffeoylquinic acid inhibits PD-1/PD-L1 interact.

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