Physicochemical Properties
| Molecular Formula | C20H20O5 |
| Molecular Weight | 340.38 |
| Exact Mass | 340.131 |
| CAS # | 68236-13-5 |
| Related CAS # | (2R/S)-6-PNG;68682-01-9 |
| PubChem CID | 155094 |
| Appearance | White to off-white solid powder |
| Density | 1.314±0.06 g/cm3 |
| LogP | 4.018 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 25 |
| Complexity | 504 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | CC(=CCC1=C(C2=C(C=C1O)O[C@@H](CC2=O)C3=CC=C(C=C3)O)O)C |
| InChi Key | YHWNASRGLKJRJJ-KRWDZBQOSA-N |
| InChi Code | InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-18-19(20(14)24)16(23)10-17(25-18)12-4-6-13(21)7-5-12/h3-7,9,17,21-22,24H,8,10H2,1-2H3/t17-/m0/s1 |
| Chemical Name | (2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one |
| Synonyms | 6-PNYS03 6-Prenylnaringenin 6Prenylnaringenin6 Prenylnaringenin |
| 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
| ln Vitro | (2S)-6-Prenylnaringenin (6-Prenylnaringenin) demonstrates low micromolar doses of regulatory action. (2S)With an IC50 value of 3.7 μM in native GABAA receptors, -6-prenylnaringenin increases GABA-induced [3H]EBOB binding displacement in a concentration-dependent manner [1]. |
| References |
[1]. Hops Compounds Modulatory Effects and 6-prenylnaringenin Dual Mode of Action on GABA AReceptors. Eur J Pharmacol. 2020 Apr 15;873:172962. |
| Additional Infomation |
6-prenylnaringenin is a trihydroxyflavanone having a structure of naringenin prenylated at C-6. It has a role as a T-type calcium channel blocker. It is a trihydroxyflavanone, a member of 4'-hydroxyflavanones and a (2S)-flavan-4-one. It is functionally related to a (S)-naringenin. 6-Prenylnaringenin has been reported in Humulus lupulus, Macaranga denticulata, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~293.80 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (7.34 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. 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 (7.34 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 (7.34 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 | 2.9379 mL | 14.6895 mL | 29.3789 mL | |
| 5 mM | 0.5876 mL | 2.9379 mL | 5.8758 mL | |
| 10 mM | 0.2938 mL | 1.4689 mL | 2.9379 mL |