Physicochemical Properties
| Molecular Formula | C15H10O5 |
| Molecular Weight | 270.2369 |
| Exact Mass | 270.053 |
| CAS # | 2034-65-3 |
| PubChem CID | 5281611 |
| Appearance | Light yellow to yellow solid powder |
| Density | 1.579g/cm3 |
| Boiling Point | 539.7ºC at 760mmHg |
| Melting Point | 310-311ºC |
| Flash Point | 210.6ºC |
| Vapour Pressure | 1.76E-12mmHg at 25°C |
| Index of Refraction | 1.747 |
| LogP | 2.576 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 20 |
| Complexity | 422 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | OBWHQJYOOCRPST-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)15-14(19)13(18)11-6-5-10(17)7-12(11)20-15/h1-7,16-17,19H |
| Chemical Name | 3,7-dihydroxy-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 | DNA |
| ln Vitro |
In the presence of Cu(II), 3,7,4'-Trihydroxyflavone induced breakage of supercoiled plasmid pBR322 DNA. [1] Cu(I) was confirmed as an essential intermediate in the DNA strand-scission process mediated by 3,7,4'-Trihydroxyflavone and Cu(II), which was verified using the Cu(I)-specific sequestering reagent neocuproine. [1] The Cu(II)-mediated DNA scission induced by 3,7,4'-Trihydroxyflavone was inhibited by the addition of catalase, while DNA strand breakage was observed upon the addition of KI and superoxide dismutase (SOD). [1] 3,7,4'-Trihydroxyflavone could induce the production of H₂O₂ and superoxide anion in the presence of Cu(II), leading to subsequent oxidative damage of DNA. [1] |
| Cell Assay |
DNA strand-scission activity assay: Supercoiled plasmid pBR322 DNA was incubated with 3,7,4'-Trihydroxyflavone in the presence of Cu(II) to detect whether the drug could cause DNA breakage. [1] Cu(I) intermediate verification assay: The Cu(I)-specific sequestering reagent neocuproine was added to the reaction system of 3,7,4'-Trihydroxyflavone, Cu(II), and pBR322 DNA to confirm the role of Cu(I) as an essential intermediate in the DNA strand-scission process. [1] Reactive oxygen species (ROS) related assay: Catalase, KI, and superoxide dismutase (SOD) were separately added to the reaction system of 3,7,4'-Trihydroxyflavone, Cu(II), and pBR322 DNA to investigate the types of ROS involved in the DNA oxidative damage induced by the drug. [1] |
| ADME/Pharmacokinetics |
Metabolism / Metabolites Resokaempferol has known human metabolites that include (2S,3S,4S,5R)-6-[4-(3,7-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid. |
| References |
[1]. Flavonoids with DNA strand-scission activity from Rhus javanica var. roxburghiana. Fitoterapia. 2008 Jan;79(1):32-6. Epub 2007 Aug 9. |
| Additional Infomation |
3,4',7-Trihydroxyflavone is a hydroxyflavan. 3,7,4'-Trihydroxyflavone has been reported in Erythrina fusca, Anthyllis vulneraria, and other organisms with data available. 3,7,4'-Trihydroxyflavone is a flavonoid isolated from the stems of Rhus javanica var. roxburghiana. [1] |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~370.04 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.25 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 (9.25 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (9.25 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 25.0 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 | 3.7004 mL | 18.5021 mL | 37.0041 mL | |
| 5 mM | 0.7401 mL | 3.7004 mL | 7.4008 mL | |
| 10 mM | 0.3700 mL | 1.8502 mL | 3.7004 mL |