Tephrosin

Names

[ CAS No. ]:
76-80-2

[ Name ]:
Tephrosin

[Synonym ]:
Tephrosin
Toxicarol
(7aR,13aR)-7a-Hydroxy-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one
3H-Bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-7a-hydroxy-9,10-dimethoxy-3,3-dimethyl-, (7aR,13aR)-
3H-Bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-7a-hydroxy-9,10-dimethoxy-3,3-dimethyl-, (7aR-cis)-
Hydroxydeguelin
(7aR-cis)-13,13a-Dihydro-7a-hydroxy-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one
3H-[1]Benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aH)-one, 13,13a-dihydro-7a-hydroxy-9,10-dimethoxy-3,3-dimethyl-, (7aR,13aR)-

Biological Activity

[Description]:

Tephrosin is a natural rotenoid which has potent antitumor activities. Tephrosin induces degradation of of EGFR and ErbB2 by inducing internalization of the receptors[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vitro]

Treatment of HT-29 cells with tephrosin (0-10μM) inhibits both the ligand-induced and constitutive phosphorylation of EGFR, ErbB2 and ErbB3, and concomitantly suppresses the activation of the downstream signaling molecules such as Akt and Erk1/2 mitogen-activated protein kinase (MAPK) [1].

[References]

[1]. Choi S, et al. Tephrosin induces internalization and degradation of EGFR and ErbB2 in HT-29 human colon cancer cells. Cancer Lett. 2010 Jul 1;293(1):23-30.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
623.4±55.0 °C at 760 mmHg

[ Melting Point ]:
198° (218-220°)

[ Molecular Formula ]:
C₂₃H₂₂O₇

[ Molecular Weight ]:
410.417

[ Flash Point ]:
219.3±25.0 °C

[ Exact Mass ]:
410.136566

[ PSA ]:
83.45000

[ LogP ]:
4.48

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.614

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H410

[ Precautionary Statements ]:
P273-P501

[ Hazard Codes ]:
N

[ Risk Phrases ]:
50

[ Safety Phrases ]:
61

[ RIDADR ]:
UN 3077 9 / PGIII

[ Hazard Class ]:
9.0

Precursor & DownStream

Precursor

DownStream

Articles

[Rotenoids from Derris trifoliata].

Zhong Yao Cai 30(6) , 660-2, (2007)

Five rotenoids named dehydrodeguelin, dehydrorotenone, 12a-hydroxy rotenone, tephrosin and 12alphabeta-hydroxyrot-2'-enonic acid were isolated from aerial parts of Derris trifoliata. All these compoun...

Preparative isolation and purification of three rotenoids and one isoflavone from the seeds of Millettia pachycarpa Benth by high-speed counter-current chromatography.

J. Chromatogr. A. 1178(1-2) , 101-7, (2008)

Both analytical and preparative high-speed counter-current chromatography (HSCCC) were used to isolate and separate chemical bioactive constituents from the seeds of Millettia pachycarpa Benth, a famo...

Effect of rotenoids from the seeds of Millettia dura on larvae of Aedes aegypti.

Pest Manag. Sci. 59(10) , 1159-61, (2003)

A crude chloroform extract of seeds of Millettia dura Dunn (Leguminosae) showed high activity (LC50 = 3.5 microg ml(-1) at 24 h) against second-instar larvae of the mosquito, Aedes aegypti L (Diptera:...