alpha-Cyperone

Names

[ CAS No. ]:
473-08-5

[ Name ]:
alpha-Cyperone

[Synonym ]:
Eudesma-4,11-dien-3-one
Eudesma-4,11-dien-3-on
2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-1,4a-dimethyl-7-(1-methylethenyl)-, (4aS,7R)-
a-Cyperone
(4aS-cis)-4,4a,5,6,7,8-Hexahydro-1,4a-dimethyl-7-(1-methylethenyl)-2(3H)-naphthalenone
(4aS,7R)-1,4a-Dimethyl-7-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-1,4a-dimethyl-7-(1-methylethenyl)-, (4aS-cis)-
Alpha-Cyperone
(4aS,7R)-7-Isopropenyl-1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone
Cyperone, α-

Biological Activity

[Description]:

Alpha-cyperone is associated with the down-regulation of COX-2,IL-6,Nck-2,Cdc42 and Rac1, resulting in reduction of inflammation. which would be highly beneficial for treatment of inflammatory diseases such as AD.In vitro: The anti-inflammatory activity of alpha-cyperone is associated with the down-regulation of COX-2 and IL-6 via the negative regulation of the NFκB pathway in LPS-stimulated RAW 264.7 cells.[1]Alpha-Cyperone binds and interacts with tubulin and is capable of distinctly destabilizing microtubule polymerization. The effect of this interaction could result in reduction of inflammation which would be highly beneficial for treatment of inflammatory diseases such as AD. One microliter of alpha-Cyperone was dissolved in DMSO (1:1 v/v) and it was further diluted in double distilled water (ddH2O) to a final volume of 20 microliter. [2]

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

Natural Products >> Terpenoids and Glycosides

[References]

[1]. Jung, S. H. et al. alpha-Cyperone, isolated from the rhizomes of Cyperus rotundus, inhibits LPS-induced COX-2 expression and PGE2 production through the negative regulation of NFkappaB signalling in RAW 264.7 cells. Journal of ethnopharmacology 147, 208-2

[2]. Azimi, A. et al. alpha-Cyperone of Cyperus rotundus is an effective candidate for reduction of inflammation by destabilization of microtubule fibers in brain. Journal of ethnopharmacology, doi:10.1016/j.jep.2016.06.058 (2016).

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
320.4±22.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₅H₂₂O

[ Molecular Weight ]:
218.335

[ Flash Point ]:
142.8±13.2 °C

[ Exact Mass ]:
218.167068

[ PSA ]:
17.07000

[ LogP ]:
4.22

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.504

[ Storage condition ]:
-20°C

Safety Information

[ Safety Phrases ]:
24/25

[ HS Code ]:
2914190090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914190090

[ Summary ]:
2914190090 other acyclic ketones without other oxygen function。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%