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Eupatilin is a naturally occurring lipophilic flavonoid isolated from Artemisia species, acting as a PPARα agonist, and possessing anti-apoptotic, anti-oxidative and anti-inflammatory activities.
| ln Vitro |
Eupatilin is a PPARα agonist. Eupatilin (10, 30, 100 μM) reduces IL-4 expression and degranulation in RBL-2H3 cells [1]. Eupatilin (50-100 μM) showed a modest reduction in HaCaT cell viability. Eupatilin (10, 30, 50, 100 μM) promotes PPARα transactivation and expression in HaCaT cells. Eupatilin (10, 30, and 50 μM) reduced TNFα-induced MMP-2/-9 expression in HaCaT cells. Eupatilin suppresses TNFα-induced p65 translocation, IκBα phosphorylation, AP-1, and MAPK signaling via PPARα [2]. Eupatilin (10-50 μM) shows no cytotoxic effects on ARPE19 cells. Eupatilin (10, 25, 50 μM) decreases H2O2-induced ROS generation in ARPE19 cells while increasing oxidation-induced cell viability. Eupatilin (50 μM) reduces H2O2-induced cell viability while activating PI3K/Akt receptors in RPE cells [3].
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| ln Vivo |
The oxazolone-induced Balb/c model exhibits improved symptoms similar to atopic dermatitis (AD) when euphemilin (1.5% or 3.0%) is administered. In the model induced by oxazolone, euphemaline significantly decreased serum IgE levels, IL-4 levels, and the mRNA expression of TNFα, IFNγ, IL-1β, TSLP, IL-33, and IL-25 induced by oxazolone. Eupatilin also raises the loricin and filaggrin mRNA expression among the compounds produced by oxazolone [1].
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Eupatilin has known human metabolites that include Jaceosidine. |
| References |
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| Additional Infomation |
Eupatilin is a trimethoxyflavone that is flavone substituted by hydroxy groups at C-5 and C-7 and methoxy groups at C-6, C-3' and C-4' respectively. Isolated from Citrus reticulata and Salvia tomentosa, it exhibits anti-inflammatory, anti-ulcer and antineoplastic activities. It has a role as an anti-ulcer drug, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antineoplastic agent, an anti-inflammatory agent and a metabolite. It is a trimethoxyflavone and a dihydroxyflavone.
Eupatilin has been reported in Artemisia princeps, Achillea setacea, and other organisms with data available. |
| Molecular Formula |
C18H16O7
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|---|---|
| Molecular Weight |
344.3154
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| Exact Mass |
344.089
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| CAS # |
22368-21-4
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| PubChem CID |
5273755
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
583.6±50.0 °C at 760 mmHg
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| Melting Point |
236 °C
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| Flash Point |
214.7±23.6 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.627
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| LogP |
2.46
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
25
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| Complexity |
520
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
DRRWBCNQOKKKOL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H16O7/c1-22-12-5-4-9(6-14(12)23-2)13-7-10(19)16-15(25-13)8-11(20)18(24-3)17(16)21/h4-8,20-21H,1-3H3
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| Chemical Name |
2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
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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) |
DMSO : ~33.33 mg/mL (~96.80 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.26 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.26 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.26 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9043 mL | 14.5214 mL | 29.0428 mL | |
| 5 mM | 0.5809 mL | 2.9043 mL | 5.8086 mL | |
| 10 mM | 0.2904 mL | 1.4521 mL | 2.9043 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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