Ferutinin

Modify Date: 2024-01-08 19:14:10

Ferutinin Structure
Ferutinin structure
Common Name Ferutinin
CAS Number 41743-44-6 Molecular Weight 358.47
Density 1.2±0.1 g/cm3 Boiling Point 489.0±45.0 °C at 760 mmHg
Molecular Formula C22H30O4 Melting Point N/A
MSDS N/A Flash Point 164.4±22.2 °C

 Use of Ferutinin


Ferutinin, a natural terpenoid compound, is an estrogen receptor ERα agonist and estrogen ERβ-receptor agonist/antagonist with IC50s of 33.1 nM and 180.5 nM, respectively. Ferutinin acts as an electrogenic Ca2+-ionophore that increases calcium permeability of lipid bilayer membranes, mitochondria. Ferutinin possesses estrogenic, antitumor, antibacterial and antiinflammatory activities[1][2].

 Names

Name ferutinin
Synonym More Synonyms

 Ferutinin Biological Activity

Description Ferutinin, a natural terpenoid compound, is an estrogen receptor ERα agonist and estrogen ERβ-receptor agonist/antagonist with IC50s of 33.1 nM and 180.5 nM, respectively. Ferutinin acts as an electrogenic Ca2+-ionophore that increases calcium permeability of lipid bilayer membranes, mitochondria. Ferutinin possesses estrogenic, antitumor, antibacterial and antiinflammatory activities[1][2].
Related Catalog
Target

ERα:33.1 nM (IC50)

ERβ:180.5 nM (IC50)

In Vitro Ferutinin manifested antiproliferative activity, inducing apoptosis in several cell types: MCF-7 estrogen-dependent cancer cells, leukemia T-cell line (Jurkat), human and mouse colon carcinoma cells (Caco-2, CT26, HT29), as well as bladder (TCC) cancer cells. Ferutinin potentiates bone mineralization, and is proposed to be used as an antiosteoporosis phytoestrogen[2]. Ferutinin considerably increases the permeability of artificial and cellular membranes to Ca2+-ions and produces apoptotic cell death in different cell lines in a mitochondria-dependent manner. Ferutinin alone (10-60 µM) also dose-dependently dissipated membrane potential. In the presence of Ca2+-ions, Ferutinin (10-60 µM) induces considerable depolarization of the inner mitochondrial membrane[2].
References

[1]. Kazuhiro Ikeda, et al. Terpenoids found in the umbelliferae family act as agonists/antagonists for ER(alpha) and ERbeta: differential transcription activity between ferutinine-liganded ER(alpha) and ERbeta. Biochem Biophys Res Commun. 2002 Feb 22;291(2):354-60.

[2]. Tatsiana Ilyich, et al. Ferutinin Induces Membrane Depolarization, Permeability Transition Pore Formation, and Respiration Uncoupling in Isolated Rat Liver Mitochondria by Stimulation of Ca 2+-Permeability. J Membr Biol. 2018 Aug;251(4):563-572.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 489.0±45.0 °C at 760 mmHg
Molecular Formula C22H30O4
Molecular Weight 358.47
Flash Point 164.4±22.2 °C
Exact Mass 358.214417
PSA 66.76000
LogP 5.72
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.573

 Synthetic Route

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Ferutinin Structure

Ferutinin

CAS#:41743-44-6

Literature: Tolstikov, G. A.; Akbutina, F. A.; Dembitskii, A. D.; Valeev, F. A.; Miftakhov, M. S. Journal of Organic Chemistry USSR (English Translation), 1992 , vol. 28, # 10 p. 1666 - 1673 Zhurnal Organicheskoi Khimii, 1992 , vol. 28, # 10 p. 2081 - 2090

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Ferutinin Structure

Ferutinin

CAS#:41743-44-6

Literature: Tolstikov, G. A.; Akbutina, F. A.; Dembitskii, A. D.; Valeev, F. A.; Miftakhov, M. S. Journal of Organic Chemistry USSR (English Translation), 1992 , vol. 28, # 10 p. 1666 - 1673 Zhurnal Organicheskoi Khimii, 1992 , vol. 28, # 10 p. 2081 - 2090

~%

Ferutinin Structure

Ferutinin

CAS#:41743-44-6

Literature: Tolstikov, G. A.; Akbutina, F. A.; Dembitskii, A. D.; Valeev, F. A.; Miftakhov, M. S. Journal of Organic Chemistry USSR (English Translation), 1992 , vol. 28, # 10 p. 1666 - 1673 Zhurnal Organicheskoi Khimii, 1992 , vol. 28, # 10 p. 2081 - 2090

 Synonyms

jaeschkeanadiol p-hydroxybenzoate
L57 GUTJ BY1&1 BQ E1 H1 JOVR DQ &&Stereoisomer
jaeschkeanadiol o-hydroxybenzoate
Benzoic acid, 4-hydroxy-, (3R,3aS,4S,8aR)-1,2,3,3a,4,5,8,8a-octahydro-3-hydroxy-6,8a-dimethyl-3-(1-methylethyl)-4-azulenyl ester
ferutinol p-hydroxybenzoate
(3R,3aS,4S,8aR)-3-Hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3,3a,4,5,8,8a-octahydro-4-azulenyl 4-hydroxybenzoate
Hecameg