7,4'-Dihydroxyflavone (7,4'-DHF) is a naturally occurring flavonoid isolated from Glycyrrhiza uralensis with various bioactivity. It acts as an eotaxin/CCL11 inhibitor, has the ability to consistently suppress eotaxin production and prevent dexamethasone (Dex)‐paradoxical adverse effects on eotaxin production.
Physicochemical Properties
| Molecular Formula | C15H10O4 |
| Molecular Weight | 254.2375 |
| Exact Mass | 254.057 |
| CAS # | 2196-14-7 |
| PubChem CID | 5282073 |
| Appearance | Light yellow to yellow solid powder |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 512.8±50.0 °C at 760 mmHg |
| Melting Point | 324-325ºC |
| Flash Point | 201.2±23.6 °C |
| Vapour Pressure | 0.0±1.4 mmHg at 25°C |
| Index of Refraction | 1.699 |
| LogP | 2.54 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 19 |
| Complexity | 382 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | LCAWNFIFMLXZPQ-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-8,16-17H |
| Chemical Name | 7-hydroxy-2-(4-hydroxyphenyl)chromen-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 |
| 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
| Targets |
7,4'-Dihydroxyflavone targets carbonyl reductase 1 (CBR1) with an IC50 of 1.2 μM [2] |
| ln Vitro |
7,4'-Dihydroxyflavone (10 μM–50 μM) dose-dependently inhibited dexamethasone (100 nM)-induced eotaxin (CCL11) production in human dermal fibroblasts: 10 μM reduced eotaxin protein levels by 32%, 25 μM by 58%, and 50 μM by 72% compared to the dexamethasone-only group [1] 7,4'-Dihydroxyflavone (50 μM) downregulated IL-4 (10 ng/mL) + dexamethasone (100 nM)-induced eotaxin mRNA expression by 65% in human fibroblasts after 24 hours of treatment [1] 7,4'-Dihydroxyflavone (1 μM–10 μM) dose-dependently inhibited CBR1 enzyme activity: 10 μM achieved 89% inhibition, and kinetic analysis revealed it acts as a competitive inhibitor (increased Km value, unchanged Vmax) [2] |
| Enzyme Assay |
CBR1 inhibitory activity assay: Recombinant human CBR1 enzyme was incubated with different concentrations of 7,4'-Dihydroxyflavone (0.1 μM–20 μM) in assay buffer containing NADPH and 4-nitrobenzaldehyde (substrate) at 37°C for 20 minutes. The reaction product was detected by measuring absorbance at 340 nm (NADPH oxidation). Inhibition rate was calculated relative to the control group, and IC50 was obtained by fitting dose-response curves. For kinetic analysis, the enzyme was incubated with fixed drug concentrations and varying substrate concentrations, and Lineweaver-Burk plots were generated to determine the inhibition type [2] |
| Cell Assay |
Eotaxin production inhibition assay: Human dermal fibroblasts were seeded in 96-well plates (1 × 10⁴ cells/well) and cultured for 24 hours. The cells were treated with 7,4'-Dihydroxyflavone (10 μM–50 μM) simultaneously with dexamethasone (100 nM) and IL-4 (10 ng/mL) for another 24 hours. Eotaxin protein levels in the supernatant were quantified by ELISA. For mRNA detection, cells were seeded in 6-well plates (2 × 10⁵ cells/well) and treated under the same conditions; total RNA was extracted for qPCR to measure eotaxin mRNA expression [1] |
| References |
[1]. The Flavonoid 7,4'-Dihydroxyflavone Prevents Dexamethasone Paradoxical Adverse Effect on Eotaxin Production by Human Fibroblasts. Phytother Res. 2017 Mar;31(3):449-458. [2]. Structure-activity relationship of flavonoids as potent inhibitors of carbonyl reductase 1 (CBR1). Fitoterapia. 2015 Mar;101:51-6. |
| Additional Infomation |
4',7-dihydroxyflavone is a dihydroxyflavone in which the two hydroxy substituents are located at positions 4' and 7. It has a role as a metabolite. 7,4'-Dihydroxyflavone has been reported in Glycyrrhiza yunnanensis, Glycyrrhiza pallidiflora, and other organisms with data available. See also: Glycyrrhiza uralensis Root (part of); Glycyrrhiza inflata root (part of). 7,4'-Dihydroxyflavone is a naturally occurring flavonoid compound found in various plants [1,2] Its mechanism in inhibiting eotaxin production involves modulating the dexamethasone/IL-4 signaling pathway in fibroblasts, preventing the paradoxical pro-inflammatory effect of dexamethasone [1] As a competitive CBR1 inhibitor, 7,4'-Dihydroxyflavone exhibits structural-activity relationship characteristics: the presence of hydroxyl groups at the 7- and 4'-positions of the flavonoid scaffold is critical for its CBR1 inhibitory activity [2] 7,4'-Dihydroxyflavone holds potential for the treatment of inflammatory diseases associated with excessive eotaxin production (e.g., allergic inflammation, asthma) and conditions involving abnormal CBR1 activity [1,2] |
Solubility Data
| Solubility (In Vitro) | DMSO : ~125 mg/mL (~491.66 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.18 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 20.8 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: ≥ 2.08 mg/mL (8.18 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. Solubility in Formulation 3: ≥ 2.08 mg/mL (8.18 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9333 mL | 19.6665 mL | 39.3329 mL | |
| 5 mM | 0.7867 mL | 3.9333 mL | 7.8666 mL | |
| 10 mM | 0.3933 mL | 1.9666 mL | 3.9333 mL |