-Ferruginol) Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C20H30O |
| Exact Mass | 286.229 |
| CAS # | 514-62-5 |
| PubChem CID | 442027 |
| Appearance | White to off-white solid powder |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 388.1±31.0 °C at 760 mmHg |
| Melting Point | 56-57℃ |
| Flash Point | 175.1±14.5 °C |
| Vapour Pressure | 0.0±0.9 mmHg at 25°C |
| Index of Refraction | 1.530 |
| LogP | 7.57 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 21 |
| Complexity | 385 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | CC(C)C1=C(C=C2C(=C1)CC[C@H]3C(C)(C)CCC[C@]23C)O |
| InChi Key | QXNWVJOHUAQHLM-AZUAARDMSA-N |
| InChi Code | InChI=1S/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1 |
| Chemical Name | (4bS,8aS)-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-3-ol |
| 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 | Ferruginol (0-160 μM) has potent antiproliferative actions on thyroid cancer cells, with a 24 hour half-life of 12 μM against the MDA-T32 cell line. It is less evident how harmful Ferruginol is to normal cells [1]. In MDA-T32 cells, ferruginol (0-24 μM; 24 hours) causes apoptotic cell death. Bcl-2 expression is downregulated and Bax expression is upregulated in a dose-dependent manner by ferruginol [1]. In MDA-T32 cells, ferruginol (0–24 μM; 24 hours) suppresses the PI3K/AKT and MAPK signaling pathways [1]. Additionally, in MDA-T32 cells, ferruginol (0–24 μM; 24 hours) induces ROS-mediated alterations in matrix metalloproteinases [1]. |
| ln Vivo | Over the course of four weeks, ferruginol (20 mg/kg; oral; daily) exhibits cardioprotective effects that include reduced apoptosis and structural damage and improved heart function. By increasing PGC-1α expression and simultaneously promoting SIRT1, enhancing deacetylase SIRT1 deacetylation, and activating the expression of PGC-1α (MB and FAO), ferruginol promotes PGC-1α-mediated mitochondrial biogenesis and fatty acid oxidation, according to transcriptome and other results[3]. |
| Cell Assay |
Cell Viability Assay[1] Cell Types: MDA-T32 cells Tested Concentrations: 0-160 μM Incubation Duration: 24 hrs (hours) Experimental Results: Exerted potent antiproliferative action against thyroid cancer cells. Apoptosis Analysis[1] Cell Types: MDA-T32 cells Tested Concentrations: 0 μM, 6 μM, 12 μM, and 24 μM Incubation Duration: 24 hrs (hours) Experimental Results: Induced apoptotic cell death of MDA-T32 cells Western Blot Analysis[1] Cell Types: MDA-T32 cells Tested Concentrations: 0 μM, 6 μM, 12 μM, and 24 μM Incubation Duration: 24 hrs (hours) Experimental Results: Blocked the MAPK and PI3K/AKT signaling pathway. |
| Animal Protocol |
Animal/Disease Models: Male C57BL/6 mice (20 g, 8-10 weeks old) with Doxorubicin (DOX)-induced cardiotoxicity (DIC)[3]. Doses: 20 mg/kg Route of Administration: Administered intragastrically (po); daily; for 4 weeks Experimental Results: Relieved Doxorubicin-induced cardiac structural and functional lesion. |
| References |
[1]. Ferruginol Diterpenoid Selectively Inhibits Human Thyroid Cancer Growth by Inducing Mitochondrial Dependent Apoptosis, Endogenous Reactive Oxygen Species (ROS) Production, Mitochondrial Membrane Potential Loss and Suppression of Mitogen-Activated Protein Kinase (MAPK) and PI3K/AKT Signaling Pathways. Med Sci Monit. 2019 Apr 21;25:2935-2942. [2]. Ferruginol Restores SIRT1-PGC-1α-Mediated Mitochondrial Biogenesis and Fatty Acid Oxidation for the Treatment of DOX-Induced Cardiotoxicity. Front Pharmacol. 2021 Nov 24;12:773834. [3]. Potential antitumor promoting diterpenoids from the stem bark of Thuja standishii. Planta Med. 2003 Jan;69(1):69-72. |
| Additional Infomation |
Ferruginol is an abietane diterpenoid that is abieta-8,11,13-triene substituted by a hydroxy group at positions 12. It has a role as an antineoplastic agent, an antibacterial agent, a protective agent and a plant metabolite. It is an abietane diterpenoid, a member of phenols, a carbotricyclic compound and a meroterpenoid. Ferruginol has been reported in Salvia miltiorrhiza, Salvia amplexicaulis, 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.) |