| Identification | Back Directory | [Name]
FERULENOL | [CAS]
6805-34-1 | [Synonyms]
FERULENOL
FERULENOL USP/EP/BP
4-Hydroxy-3-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-coumarin
4-Hydroxy-3-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]-2H-1-benzopyran-2-one
2H-1-Benzopyran-2-one, 4-hydroxy-3-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]- | [Molecular Formula]
C10H10O3 | [MDL Number]
MFCD02183471 | [MOL File]
6805-34-1.mol | [Molecular Weight]
178.185 |
| Chemical Properties | Back Directory | [Melting point ]
55-56℃ | [Boiling point ]
525.3±50.0 °C(Predicted) | [density ]
1.070±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
Off-white solid. | [pka]
4.50±1.00(Predicted) | [color ]
White to off-white | [LogP]
7.730 (est) |
| Hazard Information | Back Directory | [Uses]
Prenylated 4-hydroxycoumarin. Antitubercular antibiotic with potent activity against Mycobacteria. Exerts taxol-like and dose-dependent cytotoxicity against various human tumor cell lines. Stimulator of tubulin polymerisation in vitro and inhibitor of colchicine binding to tubulin. Antithrombotic, depressing the activity of all vitamin K-dependent coagulation factors. Shows lower acute toxicity and higher activity than warfarin. Shows hepatocyte toxicity. | [Biological Activity]
ferulenol is a prenylated 4-hydroxycoumarin derivative from ferula communis var. genuine with haemorrhagic action [1]. it has been demonstrated that ferulenol exihibits potent antimycobacterial activity [2]. | [in vitro]
ferulenol stimulated tubulin polymerization in the absence of gtp, with a less extensive polymerization profile at 100 pm concentration. ferulenol decreased radiolabeled colchicine bound by tubulin in a dose-dependent manner. ferulenol altered the normal nuclear morphology of mcf-7 cells. treatment with ferulenol (100 nm and 1 μm) for 24h induced a dose-dependent reduction of cell viability [3] | [in vivo]
in albino mice, the acute ld50s of ferulenol by single po or ip were 2,100 and 319 mg/kg bw, respectively. three days after ferulenol administration, dosed animals showed hypoprothrombinemia with internal and external hemorrhages. male mice were more sensitive to intoxication than females [4]. | [storage]
+4°C | [References]
[1] lamnaouer d, bodo b, martin m t, et al. ferulenol and ω-hydroxyferulenol, toxic coumarins from ferula communis var. genuina[j]. phytochemistry, 1987, 26(6): 1613-1615.
[2] e. mamoci, i. cavoski, v. simone, et al. chemical composition and in vitro activity of plant extracts from ferula communis and dittrichia viscosa against postharvest fungi. molecules 16(3), 2609-2625 (2011).
[3] bocca c, gabriel l, bozzo f, et al. microtubule-interacting activity and cytotoxicity of the prenylated coumarin ferulenol[j]. planta medica, 2002, 68(12): 1135-1137.
[4] fraigui o, lamnaouer d, faouzi m y. acute toxicity of ferulenol, a 4-hydroxycoumarin isolated from ferula communis l[j]. veterinary and human toxicology, 2002, 44(1): 5-7. |
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