Ferruginol
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
- 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 activity
- +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.
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