Physicochemical Properties
| Molecular Formula | C34H26O10 |
| Molecular Weight | 594.58032 |
| Exact Mass | 594.152 |
| CAS # | 3778-25-4 |
| PubChem CID | 5490003 |
| Appearance | Off-white to yellow solid powder |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 813.5±65.0 °C at 760 mmHg |
| Melting Point | 292-294℃ |
| Flash Point | 264.5±27.8 °C |
| Vapour Pressure | 0.0±3.0 mmHg at 25°C |
| Index of Refraction | 1.657 |
| Source | Cryptomeria japonica, Selaginella moellendorffii |
| LogP | 5.8 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 44 |
| Complexity | 1110 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | VXQYICLHHMETFH-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C34H26O10/c1-39-19-8-5-17(6-9-19)27-15-24(37)33-25(38)16-29(42-4)31(34(33)44-27)21-11-18(7-10-26(21)41-3)28-14-23(36)32-22(35)12-20(40-2)13-30(32)43-28/h5-16,35,38H,1-4H3 |
| Chemical Name | 5-hydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-7-methoxy-2-(4-methoxyphenyl)chromen-4-one |
| Synonyms | 7''-O-Methylsciadopitysin; 3778-25-4; 22783-08-0; W 13; Amentoflavone 7,4',7'',4'''-tetramethyl ether; 4H-1-Benzopyran-4-one, 5-hydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-7-methoxy-2-(4-methoxyphenyl)-, (+)-; 5-hydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-7-methoxy-2-(4-methoxyphenyl)chromen-4-one; 5-hydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl)-7-methoxy-2-(4-methoxyphenyl)-4H-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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | Natural biflavonoid; antioxidative; anti-inflammatory; anti-viral; anti-tumor |
| ln Vitro | Bioassay-directed fractionation of an ethanolic extract of Selaginella moellendorffii has led to the isolation of a known biflavone, ginkgetin (1). A dose-dependent inhibition was observed with 1 on the growth of OVCAR-3 (human ovarian adenocarcinoma) cells with 50% inhibition occurring at 1.8 micrograms/mL. Nonbioactive fractions yielded four additional known biflavones, amentoflavone 7,4',7",4"'-tetramethyl ether, kayaflavone, podocarpusflavone A, and amentoflavone[1]. |
| Cell Assay | Biological Assays. OVCAR-3 cells were obtained from the American Type Culture Collection (ATCC: HTB-161). HEK, HeLa, and HepG2 cells were kindly provided by the Cell Bank, Veterans General Hospital, Taipei, Taiwan. Cells were grown in RPMI 1640 medium supplemented with glutamine and 10% fetal calf serum. To perform the growth inhibition assays, cells were seeded into 12-well tissue culture plates at a density of 0.2−1 × 105 cells in 1 mL medium per well. Prior to each assay, the seeded cells were preincubated overnight at 37 °C in a humidified incubator containing 5% CO2. Each experiment was carried out in triplicate. At time zero, the spent medium was replaced with 1 mL of fresh medium containing 0.5−10 μg of test compound dissolved in DMSO. Cells were harvested for viability counting subsequent to incubation at timed intervals. The medium was removed, and the wells were rinsed with 1 mL of phosphate-buffered saline. The cells were harvested with trypsin-EDTA, suspended in culture media, and microscopically counted after the trypan blue exclusion staining. Cytotoxicity of the compounds at various concentrations was calculated as the net growth inhibition (%) of the cells relative to that of controls containing an equivalent amount of DMSO only[1]. |
| References |
[1]. Selective cytotoxicity of ginkgetin from Selaginella moellendorffii. J Nat Prod. 1997 Apr;60(4):382-4. |
| Additional Infomation | 4H-1-Benzopyran-4-one, 5-hydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-7-methoxy-2-(4-methoxyphenyl)-, (+)- has been reported in Cryptomeria japonica, Selaginella moellendorffii, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~1 mg/mL (~1.68 mM) |
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.6819 mL | 8.4093 mL | 16.8186 mL | |
| 5 mM | 0.3364 mL | 1.6819 mL | 3.3637 mL | |
| 10 mM | 0.1682 mL | 0.8409 mL | 1.6819 mL |