Physicochemical Properties
| Molecular Formula | C16H12O7 |
| Molecular Weight | 316.265 |
| Exact Mass | 316.058 |
| CAS # | 520-11-6 |
| PubChem CID | 5317284 |
| Appearance | White to yellow solid powder |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 659.1±55.0 °C at 760 mmHg |
| Melting Point | 267ºC |
| Flash Point | 250.9±25.0 °C |
| Vapour Pressure | 0.0±2.1 mmHg at 25°C |
| Index of Refraction | 1.727 |
| LogP | 1.89 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 23 |
| Complexity | 491 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | FHHSEFRSDKWJKJ-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3 |
| Chemical Name | 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | The production of IL-6, IL-8, and MCP-1 is dose-dependently inhibited by a pretreatment of nereptin, with IC50 values of 4.43, 3.42, and 4.17 μM, respectively [1]. The expression of IL-1β-induced cytokine (IL-6, IL-8, and MCP-1) mRNA levels in ARPE-19 cells is inhibited by nereptin (2.5–10 μM; 25 hours) treatment [1]. Nepetin treatment (2.5-10 μM; 1.5 h; ARPE-19 cells) dose-dependently reduced p65's nuclear translocation and the phosphorylation of IKKα/β and IκBα. In activated ARPE-19 cells, napetin lowers the amounts of phosphorylated ERK1/2, JNK, and p38 MAPK [1]. |
| Cell Assay |
RT-PCR[1] Cell Types: ARPE-19 Cell Tested Concentrations: 2.5 μM, 5 μM, 10 μM Incubation Duration: 25 hrs (hours) Experimental Results: Inhibition of the mRNA expression of IL-6, IL-8 and MCP-1 in ARPE-19 cells . Western Blot Analysis[1] Cell Types: ARPE-19 Cell Tested Concentrations: 2.5 μM, 5 μM, 10 μM Incubation Duration: 1.5 hrs (hours) Experimental Results: Dose-dependent inhibition of IKKα/β and IκBα phosphorylation and p65 nuclear translocation. Reduces the levels of phosphorylated ERK1/2, JNK and p38 MAPK in activated ARPE-19 cells. |
| ADME/Pharmacokinetics |
Metabolism / Metabolites 6-Methoxyluteolin has known human metabolites that include (2S,3S,4S,5R)-6-[2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid. |
| References |
[1]. Nepetin inhibits IL-1β induced inflammation via NF-κB and MAPKs signaling pathways in ARPE-19 cells. Biomed Pharmacother. 2018 May;101:87-93. [2]. Cytotoxic activity of nepetin, a flavonoid from Eupatorium ballotaefolium HBK. Pharmazie. 2004 Dec;59(12):965-6. |
| Additional Infomation |
6-Methoxyluteolin has been reported in Salvia plebeia, Coreopsis lanceolata, and other organisms with data available. See also: Arnica montana Flower (has part). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~125 mg/mL (~395.24 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.58 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 20.8 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1619 mL | 15.8093 mL | 31.6186 mL | |
| 5 mM | 0.6324 mL | 3.1619 mL | 6.3237 mL | |
| 10 mM | 0.3162 mL | 1.5809 mL | 3.1619 mL |