Phillygenin (Phillygenol, Phillygenol; Epipinoresinol methyl ether, Sylvatesmin, Forsythigenol) is a naturally occurringa bioactive intergradient isolated from Osmanthus fragrans, showing diverse bioactivities such as anti-inflammatory, anti-obesity and antipyretic activities. It may also reduce blood lipid levels and low density lipoprotein.
Physicochemical Properties
| Molecular Formula | C₂₁H₂₄O₆ |
| Molecular Weight | 372.41 |
| Exact Mass | 372.157 |
| CAS # | 487-39-8 |
| PubChem CID | 3083590 |
| Appearance | White to off-white solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 534.9±50.0 °C at 760 mmHg |
| Melting Point | 133ºC |
| Flash Point | 277.3±30.1 °C |
| Vapour Pressure | 0.0±1.5 mmHg at 25°C |
| Index of Refraction | 1.570 |
| LogP | 2.31 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 27 |
| Complexity | 487 |
| Defined Atom Stereocenter Count | 4 |
| SMILES | COC1=C(C=C(C=C1)[C@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C=C4)O)OC)OC |
| InChi Key | CPJKKWDCUOOTEW-YJPXFSGGSA-N |
| InChi Code | InChI=1S/C21H24O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-26-20(14(15)10-27-21)12-4-6-16(22)18(8-12)24-2/h4-9,14-15,20-22H,10-11H2,1-3H3/t14-,15-,20+,21-/m0/s1 |
| Chemical Name | 4-[(3S,3aR,6R,6aR)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol |
| Synonyms | Phillygenol,PhillygenolEpipinoresinol methyl ether, Sylvatesmin, Forsythigenol |
| 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: (1). This product requires protection from light (avoid light exposure) during transportation and storage.(2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 | 1) Compared to vincristine, phillygenin exhibits a greater inhibitory impact on mouse B16 melanoma cells [1]. 2) In the FRAP experiment, phillygenin effectively reduces free radicals and demonstrates strong scavenging activity against DPPH and ABTS. |
| ln Vivo | Intravenous injection at 5.6 mg/ml is the reference value for rats. |
| References |
[1]. Determination of phillygenin in rat plasma by high-performance liquid chromatography and its application to pharmacokinetic studies. Eur J Drug Metab Pharmacokinet, 2013 Sep, 38(3):201-7. [2]. Interaction between phillygenin and human serum albumin based on spectroscopic and molecular docking. Spectrochim Acta A Mol Biomol Spectrosc, 2012 Jan, 85(1):120-6. |
| Additional Infomation | Sylvatesmin has been reported in Lindera praecox, Forsythia koreana, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~25 mg/mL (~67.13 mM) H2O : ~0.67 mg/mL (~1.80 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3.25 mg/mL (8.73 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 32.5 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of 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: ≥ 3.25 mg/mL (8.73 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 32.5 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: ≥ 3.25 mg/mL (8.73 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 32.5 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 | 2.6852 mL | 13.4261 mL | 26.8521 mL | |
| 5 mM | 0.5370 mL | 2.6852 mL | 5.3704 mL | |
| 10 mM | 0.2685 mL | 1.3426 mL | 2.6852 mL |