| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| Other Sizes |
| Targets |
The primary targets of 3,4-di-O-caffeoyl quinic acid methyl ester are related to its antioxidant and anti-inflammatory properties. Caffeoylquinic acid derivatives are known to scavenge free radicals, chelate metal ions, and inhibit enzymes such as tyrosinase, α-glucosidase, and lipoxygenase. They may also modulate signaling pathways such as NF-κB and Nrf2. The dicaffeoyl structure may enhance activity compared to monocaffeoyl derivatives. Specific molecular targets require further elucidation.
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|---|---|
| ln Vitro |
In vitro studies have demonstrated the biological activities of dicaffeoylquinic acid derivatives. These compounds show potent antioxidant activity, scavenging DPPH, ABTS, and other free radicals. They exhibit anti-inflammatory activity through inhibition of pro-inflammatory cytokine production and suppression of inflammatory mediators. Enzyme inhibitory activities have been shown against α-glucosidase, tyrosinase, and lipoxygenase. Macroantoin F has been studied for its potential health benefits. Specific IC₅₀ values have been reported in the phytochemical literature.
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| ln Vivo |
In vivo activity of 3,4-di-O-caffeoyl quinic acid methyl ester has not been extensively documented. Dicaffeoylquinic acid derivatives are known to have various health benefits, including hypoglycemic, hepatoprotective, and anti-inflammatory effects in animal models. The methyl ester may have improved bioavailability compared to the parent acid. Specific in vivo data for Macroantoin F are limited. Further studies are needed to confirm its biological activities in vivo.
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| Enzyme Assay |
For antioxidant assays, DPPH radical scavenging, ABTS, and FRAP assays are standard methods. The compound is mixed with the radical-generating system, and the reduction in absorbance is measured. IC₅₀ values for radical scavenging are calculated. For enzyme inhibition assays (α-glucosidase, tyrosinase, lipoxygenase), the compound is incubated with the enzyme and substrate, and product formation is monitored spectrophotometrically. IC₅₀ values are calculated from dose-response curves.
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| Cell Assay |
For in vitro cell-based studies, various cell lines such as hepatocytes, macrophages, or cancer cells may be used. Cells are cultured in appropriate media and treated with serial dilutions of 3,4-di-O-caffeoyl quinic acid methyl ester. Cell viability is assessed using MTT or other assays. Markers of oxidative stress such as ROS levels, glutathione content, and lipid peroxidation may be measured. Anti-inflammatory activity may be evaluated by measuring cytokine production in stimulated cells.
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| Animal Protocol |
In vivo animal studies for this compound have not been extensively reported. For similar dicaffeoylquinic acid derivatives, mouse or rat models of oxidative stress, inflammation, diabetes, or liver injury may be used. The compound is administered via oral or intraperitoneal routes. Efficacy endpoints depend on the disease model and may include biochemical markers, histological analysis, and clinical parameters. Standard protocols can be adapted from the literature.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 3,4-di-O-caffeoyl quinic acid methyl ester have not been comprehensively characterized. As a methyl ester, it may have improved lipophilicity and oral bioavailability compared to the parent acid. The ester may be hydrolyzed by esterases to the active acid form. The compound is relatively large (MW ~516 g/mol) and polar, which may limit absorption. Specific PK parameters have not been reported. Further studies are needed.
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| Toxicity/Toxicokinetics |
Toxicological data for 3,4-di-O-caffeoyl quinic acid methyl ester are limited. As a naturally occurring phenolic compound, it is expected to have low toxicity. Caffeoylquinic acid derivatives are generally considered safe and are present in many foods. However, systematic toxicological studies have not been published. Standard safety assessments would be needed for therapeutic applications.
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| References | |
| Additional Infomation |
Methyl(1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid ester has been reported in Gelasia latifolia, Takhtajaniantha austriaca, and other organisms with available data.
3,4-Di-O-caffeoyl quinic acid methyl ester (Macroantoin F) is a research compound used in studies of phenolic compounds and their biological activities. It is a dicaffeoylquinic acid derivative found in various plants. The compound may be used as a reference standard for analytical method development or as a tool for studying antioxidant, anti-inflammatory, and enzyme inhibitory mechanisms. No clinical trials or therapeutic applications have been reported. |
| Molecular Formula |
C26H26O12
|
|---|---|
| Molecular Weight |
530.477448940277
|
| Exact Mass |
530.142
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| CAS # |
114637-83-1
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| PubChem CID |
10392218
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| Appearance |
Typically exists as solid at room temperature
|
| LogP |
1.118
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| Hydrogen Bond Donor Count |
6
|
| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
10
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| Heavy Atom Count |
38
|
| Complexity |
903
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| Defined Atom Stereocenter Count |
4
|
| SMILES |
O(C(/C=C/C1C=CC(=C(C=1)O)O)=O)[C@@H]1C[C@](C(=O)OC)(C[C@H]([C@H]1OC(/C=C/C1C=CC(=C(C=1)O)O)=O)O)O
|
| InChi Key |
PKJBSZTYNDRXEQ-VOHNXBSUSA-N
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| InChi Code |
InChI=1S/C26H26O12/c1-36-25(34)26(35)12-20(31)24(38-23(33)9-5-15-3-7-17(28)19(30)11-15)21(13-26)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h2-11,20-21,24,27-31,35H,12-13H2,1H3/b8-4+,9-5+/t20-,21-,24-,26+/m1/s1
|
| Chemical Name |
methyl (1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylate
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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 | 1.8851 mL | 9.4254 mL | 18.8509 mL | |
| 5 mM | 0.3770 mL | 1.8851 mL | 3.7702 mL | |
| 10 mM | 0.1885 mL | 0.9425 mL | 1.8851 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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