Physicochemical Properties
| Molecular Formula | C17H14O7 |
| Molecular Weight | 330.29 |
| Exact Mass | 330.073 |
| CAS # | 552-54-5 |
| PubChem CID | 5320945 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 591.6±50.0 °C at 760 mmHg |
| Melting Point | 214-215℃ |
| Flash Point | 221.2±23.6 °C |
| Vapour Pressure | 0.0±1.7 mmHg at 25°C |
| Index of Refraction | 1.681 |
| LogP | 2.26 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 24 |
| Complexity | 517 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | COC1=CC(=C2C(=C1)OC(=C(C2=O)O)C3=CC(=C(C=C3)O)OC)O |
| InChi Key | MYMGKIQXYXSRIJ-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C17H14O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-10(18)12(5-8)23-2/h3-7,18-19,21H,1-2H3 |
| Chemical Name | 3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-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 |
| 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 | VEGFR2 4.68 μM (IC50) |
| ln Vitro | HUVECs' VEGF-induced proliferation, migration, and tube formation are inhibited by rhamnazin (5–40 μM) [1]. Rhamnazin (0–20 μM) inhibits the VEGFR-2 signaling pathway and VEGFR-2 tyrosine kinase activity[1]. Rhamnazin (0–40 μM; 24 h) inhibits the VEGFR2 signaling pathway and the proliferation of breast cancer cells[1]. |
| ln Vivo | Mice treated with rhamnazin (200 mg/kg; ig; daily for 25 days) do not develop breast cancer or angiogenesis[1]. In a rat model of acute lung injury, rhamnazin (5–20 mg/kg; ip; once) exhibits potent anti-inflammatory and antioxidant properties[2]. |
| Cell Assay |
Cell Migration Assay [1] Cell Types: HUVECs Tested Concentrations: 0, 10, 15 and 20 μM Incubation Duration: 6 h Experimental Results: Strongly inhibited the migration of HUVECs. Western Blot Analysis[1] Cell Types: HUVECs Tested Concentrations: 0, 10, 15 and 20 μM Incubation Duration: 24 h Experimental Results: diminished VEGF binding to VEGFR2. diminished VEGF-stimulated phosphorylation of VEGFR2 and its downstream MAPK, AKT, and STAT3 in HUVECs in a concentrationdependent manner. Cell Proliferation Assay[1] Cell Types: HCC1937 , T-47D, SK-BR-3, MCF-7 and MDA-MB-231 Tested Concentrations: 0, 10, 15, 20, 30 and 40 μM Incubation Duration: 24 h Experimental Results: Inhibited cell growth with IC50s of 19, 27 , 32, 41 and 64 μM against MDA-MB-231, MCF-7, SK-BR-3, T-47D and HCC1937 in the presence of VEGF, respectively. |
| Animal Protocol |
Animal/Disease Models: BALB/c nude mice, breast cancer xenograft model[1] Doses: 200 mg/kg Route of Administration: intragastric (po) administration, daily for 25 days Experimental Results: Dramatically suppressed tumor volumes by 47% compared with the vehicle group. demonstrated a significant reduction of pVEGFR2Tyr951-positive cells in tumors. Resulted in downregulation of VEGFR2 downstream molecules phosphorylation including MAPK, AKT and STAT3. |
| References |
[1]. Rhamnazin, a novel inhibitor of VEGFR2 signaling with potent antiangiogenic activity and antitumor efficacy. Biochem Biophys Res Commun. 2015 Mar 20;458(4):913-9. [2]. ANTIOXIDANT AND ANTI-INFLAMMATORY EFFECTS OF RHAMNAZIN ON LIPOPOLYSACCHARIDE-INDUCED ACUTE LUNG INJURY AND INFLAMMATION IN RATS. Afr J Tradit Complement Altern Med. 2017 Jun 5;14(4):201-212. |
| Additional Infomation |
Rhamnacene is a dimethoxyflavone that is quercetin in which the hydroxy groups at the 3' and 7 positions have been replaced by methoxy groups. It has a role as a plant metabolite and an antineoplastic agent. It is a dimethoxyflavone, a trihydroxyflavone, an aromatic ether and a member of phenols. It is functionally related to a quercetin. It is a conjugate acid of a rhamnacene-3-olate. Rhamnazin has been reported in Callicarpa kwangtungensis, Halocnemum strobilaceum, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| 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 | 3.0276 mL | 15.1382 mL | 30.2764 mL | |
| 5 mM | 0.6055 mL | 3.0276 mL | 6.0553 mL | |
| 10 mM | 0.3028 mL | 1.5138 mL | 3.0276 mL |