Physicochemical Properties
| Molecular Formula | C26H30O11 |
| Molecular Weight | 518.51 |
| Exact Mass | 518.178 |
| CAS # | 52589-11-4 |
| PubChem CID | 193876 |
| Appearance | Light yellow to yellow solid powder |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 861.5±65.0 °C at 760 mmHg |
| Flash Point | 290.7±27.8 °C |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| Index of Refraction | 1.672 |
| LogP | 2.14 |
| Hydrogen Bond Donor Count | 7 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 37 |
| Complexity | 808 |
| Defined Atom Stereocenter Count | 7 |
| SMILES | CC(=CCC1=C(C=C(C2=C1O[C@@H]([C@H](C2=O)O)C3=CC=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C |
| InChi Key | GRDZTDZJQRPNCN-YIANMRPHSA-N |
| InChi Code | InChI=1S/C26H30O11/c1-11(2)3-8-14-16(35-26-23(34)21(32)19(30)17(10-27)36-26)9-15(29)18-20(31)22(33)24(37-25(14)18)12-4-6-13(28)7-5-12/h3-7,9,17,19,21-24,26-30,32-34H,8,10H2,1-2H3/t17-,19-,21+,22+,23-,24-,26-/m1/s1 |
| Chemical Name | (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-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
| ln Vitro | In U2OS and Saos-2 cells, pellamurin (0–10 μg/mL; 48 hours) treatment reduces cell viability in a dose-dependent way[1]. Phellamurin treatment (0-10 μg/mL; 48 hours; U2OS and Saos-2 cells) concentration-dependently promotes apoptosis in U2OS and Saos-2 cells[1]. Phellamurin treatment (0-10 μg/mL; 48 hours; U2OS and Saos-2 cells) reduces the ratios of p-mTOR/mTOR, p-AKT/AKT, and p-PI3K/PI3K in U2OS and Saos-2 cells[1]. |
| ln Vivo | Osteosarcoma tumor growth is inhibited in vivo by phenellamurin (50 mg/kg/day; intraperitoneal injection; daily; for 21 days; female BALB/c nude mice). Phellamurin-treated animals have lower ratios of p-PI3K/PI3K, p-AKT/AKT, and p-mTOR/mTOR in xenografts[1]. |
| Cell Assay |
Cell Viability Assay[1] Cell Types: U2OS and Saos-2 cells Tested Concentrations: 0 μg/mL, 2.5 μg/mL, 5 μg/mL, and 10 μg/mL Incubation Duration: 48 hrs (hours) Experimental Results: Suppressed the viability of U2OS and Saos-2 cells in a concentration-dependent manner. Apoptosis Analysis[1] Cell Types: U2OS and Saos-2 cells Tested Concentrations: 0 μg/mL, 2.5 μg/mL, 5 μg/mL, and 10 μg /mL Incubation Duration: 48 hrs (hours) Experimental Results: Induced apoptosis of U2OS and Saos-2 cells in a concentration-dependent manner. Western Blot Analysis[1] Cell Types: U2OS and Saos-2 cells Tested Concentrations: 0 μg/mL and 10 μg/ mL Incubation Duration: 48 hrs (hours) Experimental Results: Repressed the PI3K/AKT/mTOR pathway in U2OS and Saos-2 cells. |
| Animal Protocol |
Animal/Disease Models: Athymic female BALB/c nude mice (6 weeks old ) injected with U2OS cells[1] Doses: 50 mg/kg/day Route of Administration: intraperitoneal (ip)injection; daily; for 21 days Experimental Results: Repressed osteosarcoma tumor growth in vivo. |
| References |
[1]. Anti-tumor Efficacy of Phellamurin in Osteosarcoma Cells: Involvement of the PI3K/AKT/mTOR Pathway. Eur J Pharmacol. 2019 Sep 5;858:172477. [2]. Marked Decrease of Cyclosporin Absorption Caused by Phellamurin in Rats. Planta Med. 2002 Feb;68(2):138-41. [3]. Synergistic or Antagonistic Modulation of Oviposition Response of Two Swallowtail Butterflies, Papilio Maackii and P. Protenor, to Phellodendron Amurense by Its Constitutive Prenylated Flavonoid, Phellamurin. J Chem Ecol. 2011 Jun;37(6):575-81. |
| Additional Infomation |
Phellamurin is a member of the class of dihydroflavonols that is (+)-dihydrokaempferol substituted by a prenyl group at position 8 and a beta-D-glucopyranosyl group at position 7 via a glycosidic linkage. Isolated from Phellodendron amurense and Commiphora africana, it exhibits inhibition of intestinal P-glycoprotein. It has a role as a metabolite. It is a member of dihydroflavonols, a flavanone glycoside, a trihydroxyflavanone, a monosaccharide derivative, a beta-D-glucoside and a member of 4'-hydroxyflavanones. It is functionally related to a (+)-dihydrokaempferol. Phellamurin has been reported in Phellodendron chinense var. glabriusculum, Phellodendron amurense var. wilsonii, 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 | 1.9286 mL | 9.6430 mL | 19.2860 mL | |
| 5 mM | 0.3857 mL | 1.9286 mL | 3.8572 mL | |
| 10 mM | 0.1929 mL | 0.9643 mL | 1.9286 mL |