|
|
| | Ferruginol Basic information |
| Product Name: | Ferruginol | | Synonyms: | 3-Phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-(1-methylethyl)-, (4bS,8aS)-;(+)-8,11,13-Abietatrien-12-ol;(4aS)-1,1,4aβ-Trimethyl-7-isopropyl-1,2,3,4,4a,9,10,10aα-octahydrophenanthrene-6-ol;(4bS)-4b,5,6,7,8,8aβ,9,10-Octahydro-4b,8,8-trimethyl-2-isopropylphenanthren-3-ol;8,11,13-Abietatriene-12-ol;abieta-8,11,13-triene-12-ol;ferruginol | | CAS: | 514-62-5 | | MF: | C20H30O | | MW: | 286.45 | | EINECS: | | | Product Categories: | | | Mol File: | 514-62-5.mol |  |
| | Ferruginol Chemical Properties |
| Melting point | 56-57℃ | | Boiling point | 388.1±31.0 °C(Predicted) | | density | 0.988±0.06 g/cm3 (20 ºC 760 Torr) | | solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | | form | Powder | | pka | 10.89±0.60(Predicted) | | color | White to off-white | | Optical Rotation | +40.616 (c4, ethanol) | | InChI | 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 | | InChIKey | QXNWVJOHUAQHLM-AZUAARDMSA-N | | SMILES | C1=C2C([C@]3(C)[C@@]([H])(CC2)C(C)(C)CCC3)=CC(O)=C1C(C)C |
| | Ferruginol Usage And Synthesis |
| Uses | Ferruginol can be used for its antibacterial activities. | | Definition | ChEBI: 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. | | Synthesis | Stereospecific syntheses of (±)-ferruginol and (±)-hinokione were achieved in which the tricyclic ring system was assembled in the order C - BC - ABC. The key features of the approach involve: (1) the utilization of a lactone bridge as part of an enone protecting group in ring A; (2) the installation of an isopropyl group by the regioselective addition of lithium dimethylcuprate to a cross-conjugated dienone; (3) the elimination of the lactone bridge with concomitant aromatization of ring C; and (4) the reductive methylation of the enone in ring A to install the C-4 geminal dimethyl group and to guarantee the trans fusion of the AB rings.
 | | in vivo | Ferruginol (20 mg/kg; p.o.; daily; for 4 weeks) exerts cardioprotection manifested as enhanced cardiac function and reduced structural damage and apoptosis. The transcriptome and other results revealed that Ferruginol facilitates PGC-1α-mediated mitochondrial biogenesis and fatty acid oxidation (MB and FAO) by increasing the expression of PGC-1α and concurrently promoting the expression of SIRT1-enhancing deacetylase SIRT1 deacetylating and activating PGC-1α[3]. | Animal Model: | Male C57BL/6 mice (20 g, 8-10 weeks old) with Doxorubicin (DOX)-induced cardiotoxicity (DIC)[3]. | | Dosage: | 20 mg/kg | | Administration: | Administered intragastrically; daily; for 4 weeks | | Result: | Relieved Doxorubicin-induced cardiac structural and functional lesion. |
| | target | PARP | Bcl-2/Bax | Caspase | Antifection | | References | [1] DAVID L. SNITMAN David S W Richard J Himmelsbach. Total synthesis of (.+-.)-ferruginol and (.+-.)-hinokione[J]. The Journal of Organic Chemistry, 1978, 43 25: 4758-4762. DOI:10.1021/jo00419a011. |
| | Ferruginol Preparation Products And Raw materials |
|