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| Targets |
The biological target of (+)-Catechin pentaacetate is primarily related to its parent compound, (+)-catechin. (+)-Catechin inhibits cyclooxygenase-1 (COX-1), an enzyme involved in the production of prostaglandins and thromboxanes, with an IC50 of 1.4 μM. COX-1 is a key enzyme in the arachidonic acid pathway and is a target for non-steroidal anti-inflammatory drugs. As a flavonoid, (+)-catechin and its derivatives may also interact with various other enzymes and signaling pathways, often exhibiting antioxidant properties by scavenging free radicals. The pentaacetate derivative may act as a prodrug, being deacetylated in vivo to release the active (+)-catechin. The compound may also affect iron and zinc transporter expression in the duodenum.
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| ln Vitro |
In vitro, (+)-Catechin pentaacetate is used as a precursor for the production of (+)-catechin. The parent compound (+)-catechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. (+)-Catechin is a useful natural herbicide and antimicrobial agent. As a flavonoid, (+)-catechin also exhibits antioxidant activity, which is typically assessed in cell-free assays such as DPPH, ABTS, or FRAP assays. The pentaacetate derivative may have improved cellular permeability compared to the parent compound due to the acetyl groups, which can be hydrolyzed by cellular esterases to release the active flavonoid. However, specific quantitative activity data for the pentaacetate derivative itself are limited.
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| ln Vivo |
In vivo, (+)-Catechin pentaacetate has the potential to improve gut morphology and function and positively modulate the microbiome. It can reduce duodenal iron and zinc transporter expression. The compound is an esterification derivative of catechin, and the acetyl groups may enhance oral bioavailability by improving lipophilicity and membrane permeability. Once absorbed, the compound is likely deacetylated to release (+)-catechin, which then exerts its biological effects. However, specific animal model studies, dosing regimens, and quantitative outcomes have not been extensively reported in the available literature. Further in vivo studies would be required to fully characterize its efficacy, safety, and pharmacokinetic properties.
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| Enzyme Assay |
In vitro enzyme assay protocols for (+)-Catechin pentaacetate would typically involve assessing the activity of its parent compound, (+)-catechin. For COX-1 inhibition, a standard protocol would involve incubating recombinant COX-1 enzyme with varying concentrations of (+)-catechin (typically 0.1 to 100 μM) and arachidonic acid as substrate. The production of prostaglandins is measured using ELISA or other detection methods, and IC50 values are determined from concentration-response curves. For antioxidant activity, DPPH, ABTS, or FRAP assays can be used. For the pentaacetate derivative, esterase-mediated deacetylation can be assessed by incubating the compound with cellular extracts or purified esterases and monitoring the release of (+)-catechin by HPLC.
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| Cell Assay |
In vitro cell-based assay protocols for (+)-Catechin pentaacetate typically involve treating cultured cells with the compound to assess its biological effects. A standard protocol would involve seeding intestinal epithelial cells or other cell lines in multi-well plates and treating them with varying concentrations of (+)-Catechin pentaacetate (typically 1-100 μM) for 24-72 hours. Cell viability is assessed using MTT or similar assays. The effects on iron and zinc transporter expression can be measured by qPCR or Western blot. For antioxidant studies, cells are treated with the compound and then exposed to oxidative stress (e.g., H2O2), and reactive oxygen species levels are measured using fluorescent probes. Appropriate controls include vehicle-treated cells and cells treated with (+)-catechin for comparison.
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| Animal Protocol |
In vivo animal experimental protocols for (+)-Catechin pentaacetate have not been extensively reported in the available literature. Based on its potential to improve gut morphology and function, potential studies might involve administering the compound orally to rodents and assessing intestinal health parameters. A hypothetical protocol would involve administering (+)-Catechin pentaacetate by oral gavage at doses determined from preliminary studies (e.g., 10-100 mg/kg) daily for 2-4 weeks. Endpoints would include intestinal morphology (villus height, crypt depth), assessment of iron and zinc transporter expression in the duodenum by qPCR or Western blot, analysis of the gut microbiome composition by 16S rRNA sequencing, and assessment of systemic markers of inflammation and oxidative stress. Appropriate controls would include vehicle-treated groups and groups treated with (+)-catechin for comparison.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of (+)-Catechin pentaacetate have not been extensively characterized in published studies. The compound has a molecular weight of 500.45 and a molecular formula of C25H24O11. As a pentaacetate derivative, the compound is more lipophilic than the parent (+)-catechin, which may enhance oral bioavailability and cellular permeability. The acetyl groups are likely hydrolyzed by esterases in the gastrointestinal tract and liver to release the active (+)-catechin. Specific PK parameters such as half-life, Cmax, AUC, bioavailability, volume of distribution, and clearance have not been reported. The compound's metabolism, protein binding, and routes of elimination remain to be characterized. Further pharmacokinetic studies would be required to understand its absorption, distribution, metabolism, and excretion profile.
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| References | |
| Additional Infomation |
According to reports, Begonia glauca, Begonia multiflora, and other organisms with available data contain catechin pentaacetate.
(+)-Catechin pentaacetate is a research-grade compound used as a precursor for the production of (+)-catechin. It is an esterification derivative of catechin with potential to improve gut morphology and function and positively modulate the microbiome. The parent compound (+)-catechin inhibits COX-1 with an IC50 of 1.4 μM and is a useful natural herbicide and antimicrobial agent. (+)-Catechin pentaacetate has not entered clinical trials and is not approved for any therapeutic indication. Its mechanism of action is likely related to the release of (+)-catechin upon deacetylation, which then exerts COX-1 inhibitory, antioxidant, and antimicrobial effects. The compound is available exclusively for research purposes and is not intended for diagnostic, therapeutic, or human applications. |
| Molecular Formula |
C25H24O11
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| Molecular Weight |
500.45
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| Exact Mass |
500.131
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| CAS # |
16198-01-9
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| PubChem CID |
5315742
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
624.2±55.0 °C at 760 mmHg
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| Flash Point |
266.6±31.5 °C
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| Vapour Pressure |
0.0±1.8 mmHg at 25°C
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| Index of Refraction |
1.579
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| LogP |
1.08
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
11
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| Heavy Atom Count |
36
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| Complexity |
855
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CC(=O)O[C@H]1CC2=C(C=C(C=C2OC(=O)C)OC(=O)C)O[C@@H]1C3=CC(=C(C=C3)OC(=O)C)OC(=O)C
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| InChi Key |
BKYWAYNSDFXIPL-LOSJGSFVSA-N
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| InChi Code |
InChI=1S/C25H24O11/c1-12(26)31-18-9-21(33-14(3)28)19-11-24(35-16(5)30)25(36-22(19)10-18)17-6-7-20(32-13(2)27)23(8-17)34-15(4)29/h6-10,24-25H,11H2,1-5H3/t24-,25+/m0/s1
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| Chemical Name |
[(2R,3S)-5,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-3,4-dihydro-2H-chromen-3-yl] acetate
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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) |
Typically soluble in DMSO (e.g. 10 mM)
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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 | 1.9982 mL | 9.9910 mL | 19.9820 mL | |
| 5 mM | 0.3996 mL | 1.9982 mL | 3.9964 mL | |
| 10 mM | 0.1998 mL | 0.9991 mL | 1.9982 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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