Coniferyl ferulate

CAS# 63644-62-2

Coniferyl ferulate

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Quality Control of Coniferyl ferulate

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Chemical structure

Coniferyl ferulate

3D structure

Chemical Properties of Coniferyl ferulate

Cas No. 63644-62-2 SDF Download SDF
PubChem ID 6441913 Appearance Powder
Formula C20H20O6 M.Wt 356.37
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
SMILES COC1=C(C=CC(=C1)C=CCOC(=O)C=CC2=CC(=C(C=C2)O)OC)O
Standard InChIKey PGLIMMMHQDNVRS-YZQQHVNFSA-N
Standard InChI InChI=1S/C20H20O6/c1-24-18-12-14(5-8-16(18)21)4-3-11-26-20(23)10-7-15-6-9-17(22)19(13-15)25-2/h3-10,12-13,21-22H,11H2,1-2H3/b4-3+,10-7+
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 Coniferyl ferulate

The herbs of Ligusticum chuanxiong Hort.

Biological Activity of Coniferyl ferulate

Description1. Coniferyl ferulate can inhibit Glutathione S-transferase activity in a concentration-dependent manner and show a potential MDR reversal effect for antitumour adjuvant therapy.
TargetsP-gp

Coniferyl ferulate Dilution Calculator

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Coniferyl ferulate Molarity Calculator

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Preparing Stock Solutions of Coniferyl ferulate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8061 mL 14.0304 mL 28.0607 mL 56.1214 mL 70.1518 mL
5 mM 0.5612 mL 2.8061 mL 5.6121 mL 11.2243 mL 14.0304 mL
10 mM 0.2806 mL 1.403 mL 2.8061 mL 5.6121 mL 7.0152 mL
50 mM 0.0561 mL 0.2806 mL 0.5612 mL 1.1224 mL 1.403 mL
100 mM 0.0281 mL 0.1403 mL 0.2806 mL 0.5612 mL 0.7015 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 Coniferyl ferulate

Effect of different drying methods on the quality of Angelicae Sinensis Radix evaluated through simultaneously determining four types of major bioactive components by high performance liquid chromatography photodiode array detector and ultra-high performance liquid chromatography quadrupole time-of-flight mass spectrometry.[Pubmed:24561333]

J Pharm Biomed Anal. 2014 Jun;94:77-83.

In the present study, the effect of drying methods on the quality of Angelicae Sinensis Radix (DG), was evaluated by newly developed high performance liquid chromatography photodiode array detector (HPLC-DAD) and ultra-high performance liquid chromatography quadrupole time-of-flight mass spectrometry (UHPLC-QTOF-MS/MS). Ten major bioactive components including two phenolic acids, two hydroxyl phthalides, four alkyl phthalides and two phthalide dimers were selected as evaluation chemical markers and the newly-established method was qualitatively and quantitatively validated. DG slices and whole roots dried in shade, sun light, hot air, vacuum, microwave, far infrared ray and combination of microwave and far infrared ray as well as the fresh DG samples were determined by the established methods. DG slices dried in hot air kept the similar chemical composition to that of fresh DG, while DG whole roots dried in vacuum retained highest contents of the major components. Coniferyl ferulate and ligustilide degraded significantly in DG slices dried by microwave, far infrared ray and their combination. The influence of such chemical changes induced by different drying methods on the bioactivities of DG warrants further investigation, so that the optimal drying method can be obtained for the standardization of DG herb.

Investigation of the inhibitors of histone-lysine N-methyltransferase SETD2 for acute lymphoblastic leukaemia from traditional Chinese medicine.[Pubmed:27218135]

SAR QSAR Environ Res. 2016 Jul;27(7):589-608.

Leukaemia is the leading cause of childhood malignancies. Recent research indicates that the SETD2 gene is associated with acute lymphoblastic leukaemia. This study aims to identify potential lead compounds from traditional Chinese medicine (TCM) using virtual screening for SET domain containing 2 (SETD2) protein against acute lymphoblastic leukaemia. Docking simulation was performed to determine potential candidates which obtain suitable docking poses in the binding domain of the SETD2 protein. We also performed molecular dynamics (MD) simulation to investigate the stability of docking poses of SETD2 protein complexes with the top three TCM candidates and a control. According to the results of docking and MD simulation, coniselin and Coniferyl ferulate have high binding affinity and stable interactions with the SETD2 protein. Coniselin is isolated from the alcoholic extract of Comiselinum vaginatum Thell. Coniferyl ferulate can be isolated from Angelica sinensis, Poria cocos (Schw.) Wolf, and Notopterygium forbesii. Although S-adenosyl-L-homocysteine has more stable interactions with key residues in the binding domain than coniselin and Coniferyl ferulate during MD simulation, the TCM compounds coniselin and Coniferyl ferulate are still potential candidates as lead compounds for further study in the drug development process with the SETD2 protein against acute lymphoblastic leukaemia.

[Establishment and application of HPLC-QAMS for quality evaluation of Chuanxiong Rhizoma].[Pubmed:26521448]

Yao Xue Xue Bao. 2015 Jun;50(6):749-54.

A quantitative analysis method of multi-components with a single marker (QAMS) for simultaneous determination of six marker compounds (one from phenolic acids and five from phthalides) in Chuanxiong Rhizoma was established by applying HPLC and using butylidenephthalide as the internal reference substance. And also the feasibility and accuracy of the established method for quality evaluation and application of Chuanxiong Rhizoma were investigated and validated. The analysis was performed with the mobile phase consisting of acetonitrile - 0.2% aqueous formic acid. The flow rate was 1.0 mL . min-1 and the column temperature was maintained at 30 degrees C. The detection wavelengths were set at 252 nm (for ferulic acid, Z-ligustilide, and butylidenephthalide) and 266 nm (for senkyunolide I, senkyunolide A, and Coniferyl ferulate), separately, and 20 microL was injected for analysis with gradient elution. The results showed that there were no significant differences observed between the HPLC-QAMS method and the external standard method (RSD <5%). The relative correction factors were credible (RSD < 5%) in changed chromatographic conditions. The established HPLC-QAMS method can be accurately used for simultaneously evaluating and controlling the quality of Chuanxiong Rhizoma with multi-components.

Development of a sensitive LC-MS/MS method for quantification of coniferyl ferulate and its metabolite coniferyl alcohol in rat plasma: Application to a pharmacokinetic study.[Pubmed:28886520]

J Pharm Biomed Anal. 2017 Nov 30;146:201-205.

A rapid and simple LC-MS/MS method was developed and validated for the simultaneous determination of Coniferyl ferulate (CF) and its metabolite coniferyl alcohol (CA) using bavachromene as an internal standard (IS). A TSQ Quantum Access mass spectrometer was operated under selected-reaction monitoring mode using negative electrospray ionization. Extraction with ether was used in sample preparation. The plasma samples were prepared and then chromatographed on a Phenomenex Luna C18 column (2.1mmx50mm, 1.7mum; Torrance, USA) at 35 degrees C, using acetonitrile: water (65:35, v/v) in an isocratic mode at a flow rate of 0.3mL/min. Method validation was performed as per the FDA guidelines and calibration curves showed good linearity over the concentration range of 2.5-1000ng/mL for both CF and CA. The intra- and inter-day precision and accuracy were within the acceptable limits. The developed assay was successfully applied to a pharmacokinetic study of CA in rats.

Comparative analysis of Danggui and European Danggui using nuclear magnetic resonance-based metabolic fingerprinting.[Pubmed:25462119]

J Pharm Biomed Anal. 2015 Jan 25;103:44-51.

Danggui is a widely used herbal drug in traditional Chinese medicine, and adulteration with European Danggui is frequently encountered in the market. We compared the chemical compositions and biological effects of Danggui and European Danggui using proton nuclear magnetic resonance spectroscopy coupled with multivariate analysis. Results showed that Danggui and European Danggui differed in both primary and secondary metabolites. Danggui contained higher levels of alanine, gamma-aminobutyrate, adenosine, arginine, sucrose, alpha-glucose, beta-glucose, tryptophan, and cis-Z,Z'-3a.7a',7a.3a'-dihydroxyligustilide than European Danggui. Meanwhile, European Danggui contained higher contents of valine, proline, fumaric acid, phenylalanine, nicotinamide derivative, Z-butylidenephthalide, Coniferyl ferulate, ferulic acid, Z-ligustilide, and Z,Z-6,6'7,3a-diligustilide than Danggui. A blood deficiency model was used to compare the biological effects of the two drugs. Despite its higher levels of Z-ligustilide and ferulic acid, European Danggui showed a weaker blood enriching effect than Danggui. Thus, the bioactive compounds responsible for the blood enriching effect in Danggui and their possible synergistic effects should be further studied.

Coniferyl Ferulate, a Strong Inhibitor of Glutathione S-Transferase Isolated from Radix Angelicae sinensis, Reverses Multidrug Resistance and Downregulates P-Glycoprotein.[Pubmed:24058374]

Evid Based Complement Alternat Med. 2013;2013:639083.

Glutathione S-transferase (GST) is the key enzyme in multidrug resistance (MDR) of tumour. Inhibition of the expression or activity of GST has emerged as a promising therapeutic strategy for the reversal of MDR. Coniferyl ferulate (CF), isolated from the root of Angelica sinensis (Oliv.) Diels (Radix Angelicae sinensis, RAS), showed strong inhibition of human placental GST. Its 50% inhibition concentration (IC50) was 0.3 mu M, which was greater than a known GSTP1-1 inhibitor, ethacrynic acid (EA), using the established high-throughput screening model. Kinetic analysis and computational docking were used to examine the mechanism of GST inhibition by CF. Computational docking found that CF could be fully docked into the gorge of GSTP1-1. The further exploration of the mechanisms showed that CF was a reversible noncompetitive inhibitor with respect to GSH and CDNB, and it has much less cytotoxicity. Apoptosis and the expression of P-gp mRNA were evaluated in the MDR positive B-MD-C1 (ADR+/+) cell line to investigate the MDR reversal effect of CF. Moreover, CF showed strong apoptogenic activity and could markedly decrease the overexpressed P-gp. The results demonstrated that CF could inhibit GST activity in a concentration-dependent manner and showed a potential MDR reversal effect for antitumour adjuvant therapy.

Description

Coniferyl ferulate, a strong inhibitor of glutathione S-transferase (GST) isolated from Radix Angelicae sinensis, reverses multidrug resistance and downregulates P-glycoprotein. Coniferyl ferulate shows strong inhibition of human placental GST with an IC50 of 0.3 μM.

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