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| 5mg |
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| 10mg |
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| Targets |
The primary targets of 5-O-(E)-p-Coumaroylquinic acid include hepatitis B virus, inflammatory pathways, and oxidative stress pathways. It is a potent phytochemical agent against hepatitis B virus. The compound modulates oxidative and signaling pathways affecting viral susceptibility. It has anti-inflammatory activity and potential applications in preventing oxidative stress-related diseases.
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| ln Vitro |
5-O-(E)-p-Coumaroylquinic acid (compound 12) lowers the amounts of HBV DNA in mature HBV particles that are liberated from HepG2.2.15 cells.
In vitro, 5-O-(E)-p-Coumaroylquinic acid demonstrates quantifiable anti-HBV activity by significantly reducing the amount of HBV DNA in mature viral particles released from HepG2.2.15 cell cultures. It is a potent phytochemical agent against hepatitis B virus. The compound's anti-HBV activity is concentration-dependent and has been characterized in cell-based assays. |
| ln Vivo |
In vivo activity of 5-O-(E)-p-Coumaroylquinic acid has not been extensively characterized. As an anti-inflammatory compound with anti-HBV activity, it has potential therapeutic applications in preventing oxidative stress-related diseases such as cardiovascular and neurodegenerative disorders, and may have benefits in traditional medicine. However, detailed in vivo pharmacokinetic and pharmacodynamic studies are limited.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for 5-O-(E)-p-Coumaroylquinic acid are not typically performed, as the compound is primarily studied for its anti-HBV and anti-inflammatory activities in cell-based assays. Quality control assays involve HPLC to verify purity (≥99%) and identity. The compound is tested for solubility and stability under standard storage conditions.
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| Cell Assay |
In vitro cellular assays for 5-O-(E)-p-Coumaroylquinic acid involve testing its anti-HBV activity. HepG2.2.15 cells are treated with serial dilutions of the compound (0.1-100 µM) for 48-72 hours. HBV DNA levels in mature viral particles are measured by qPCR. The compound demonstrates concentration-dependent reduction of HBV DNA in released viral particles.
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| Animal Protocol |
In vivo animal studies for 5-O-(E)-p-Coumaroylquinic acid are limited, as the compound is primarily studied in vitro. For efficacy testing, animal models of HBV infection or inflammation could be used. Animals would be treated with the compound via oral or intraperitoneal administration at various doses, and viral loads or inflammatory markers would be assessed. However, detailed in vivo protocols are not well established in the available literature.
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| ADME/Pharmacokinetics |
5-O-(E)-p-Coumaroylquinic acid has a molecular formula of C16H18O8 and a molecular weight of 338.31. It appears as a solid with a purity of ≥99%. The compound is a quinic acid derivative found in plants. Information concerning product stability, particularly in solution, has rarely been reported and in most cases only a general guide can be offered. It is intended for research use only and is not for human consumption.
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| Toxicity/Toxicokinetics |
The toxicity profile of 5-O-(E)-p-Coumaroylquinic acid has not been extensively characterized. As a natural product, it is generally considered to have low toxicity. Standard toxicity studies would include assessment of acute oral toxicity, dermal irritation, and repeated-dose toxicity in animal models. The compound is intended for research use only and is not approved for clinical use.
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| References | |
| Additional Infomation |
5-Coumaroylquinic acid is a cinnamic ester formed by the condensation of the carboxyl group of 4-coumaric acid with the 5-hydroxyl group of (-)-quinic acid. It is a metabolite. It is a cinnamic ester and a cyclic alcohol carboxylic acid. Its function is related to that of (-)-quinic acid and 4-coumaric acid.
Trans-5-O-(4-coumaryl)-D-quinic acid has been reported in cherry (Prunus cerasus), peach (Prunus persica), and other organisms with relevant data. 5-O-(E)-p-Coumaroylquinic acid (CAS 5746-55-4) is a quinic acid derivative that is a potent phytochemical agent against hepatitis B virus. It has a molecular formula of C16H18O8 and a molecular weight of 338.31. The compound demonstrates quantifiable anti-HBV activity by reducing HBV DNA in mature viral particles from HepG2.2.15 cell cultures. It also has anti-inflammatory activity and potential applications in preventing oxidative stress-related diseases. It is intended for research use only and is not approved for clinical use. |
| Molecular Formula |
C16H18O8
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|---|---|
| Molecular Weight |
338.31
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| Exact Mass |
338.1
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| CAS # |
5746-55-4
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| PubChem CID |
6441280
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
613.2±55.0 °C at 760 mmHg
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| Flash Point |
227.0±25.0 °C
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| Vapour Pressure |
0.0±1.9 mmHg at 25°C
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| Index of Refraction |
1.662
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| LogP |
0.1
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
24
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| Complexity |
496
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC=C(C=C2)O)O)O
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| InChi Key |
BMRSEYFENKXDIS-OTCYKTEZSA-N
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| InChi Code |
InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14-,16+/m1/s1
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| Chemical Name |
(1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9559 mL | 14.7793 mL | 29.5587 mL | |
| 5 mM | 0.5912 mL | 2.9559 mL | 5.9117 mL | |
| 10 mM | 0.2956 mL | 1.4779 mL | 2.9559 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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