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Ferulenol

Names

[ CAS No. ]:
6805-34-1

[ Name ]:
Ferulenol

[Synonym ]:
4-hydroxy-3-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-2H-1-benzopyran-2-one
Ferulenol
prenylated 4-hydroxycoumarin
E,E-3-farnesyl-4-hydroxycoumarin

Biological Activity

[Description]:

Ferulenol, a sesquiterpene prenylated coumarin derivative, specifically inhibits succinate ubiquinone reductase at the level of the ubiquinonecycle. Ferulenol shows good antimycobacterial activity and haemorrhagic action[1][2][3].

[Related Catalog]:

Research Areas >> Infection

[In Vitro]

Ferulenol inhibits the oxidative phosphorylation process by interacting with adenine nucleotide translocase (ANT) and the complex II of the respiratory chain. At low concentrations, ferulenol inhibited ATP synthesis by inhibition of the adenine nucleotide translocase without limitation of mitochondrial respiration. At higher concentrations, ferulenol inhibited oxygen consumption. Ferulenol caused specific inhibition of succinate ubiquinone reductase without altering succinate dehydrogenase activity of the complex II[1]. Ferulenol inhibits succinate ubiquinone reductase(SQR) activity in a concentration-dependent manner and is as effective as thenoyltrifluoroacetone (TTFA)[1].

[References]

[1]. Lahouel M, et al. Ferulenol specifically inhibits succinate ubiquinone reductase at the level of the ubiquinonecycle. Biochem Biophys Res Commun. 2007 Mar 30;355(1):252-7.

[2]. Mamoci E, et al. Chemical composition and in vitro activity of plant extracts from Ferula communis and Dittrichia viscosa against postharvest fungi. Molecules. 2011 Mar 22;16(3):2609-25.

[3]. DrissLamnaouer, et al. Ferulenol and ω-hydroxyferulenol, toxic coumarins from Ferula communis var. genuine. Volume 26, Issue 6, 1987, Pages 1613-1615.

Chemical & Physical Properties

[ Density]:
1.07g/cm3

[ Boiling Point ]:
492.8ºC at 760 mmHg

[ Molecular Formula ]:
C24H30O3

[ Molecular Weight ]:
366.49300

[ Flash Point ]:
161.7ºC

[ Exact Mass ]:
366.21900

[ PSA ]:
50.44000

[ LogP ]:
6.46030

[ Index of Refraction ]:
1.559

Safety Information

[ HS Code ]:
2932209090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2932209090

[ Summary ]:
2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%


Related Compounds