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Taraxeryl acetate

Names

[ CAS No. ]:
2189-80-2

[ Name ]:
Taraxeryl acetate

[Synonym ]:
Taraxerol monoacetate
3-Picenol, 1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-eicosahydro-4,4,6a,8a,11,11,12b,14b-octamethyl-, acetate, (3S,4aR,6aR,8aR,12aR,12bS,14aR,14bR)-
Friedoolean-14-en-3-yl acetate
D-Friedoolean-14-en-3beta-yl acetate
Acetyl taraxerol
Taraxerol Acetate
Taraxenol acetate
(3S,4aR,6aR,8aR,12aR,12bS,14aR,14bR)-4,4,6a,8a,11,11,12b,14b-Octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydro-3-picenyl acetate
(3S,4aR,6aR,8aR,12aR,12bS,14aR,14bR)-4,4,6a,8a,11,11,12b,14b-Octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicen-3-yl acetate
taraxeryl acetate

Biological Activity

[Description]:

Taraxerol acetate is a COX-1 and COX-2 inhibitor with IC50 values of 116.3 μM and 94.7 μM, respectively. Taraxerol acetate the has the anticancer potential and induces cell apoptosis[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> Immunology/Inflammation >> COX

[Target]

COX-1:116.3 μM (IC50)

COX-2:94.7 μM (IC50)


[In Vitro]

Taraxerol acetate(10-150 µM; 24 or 48 hours) induces a dose- and time-dependent cytotoxic effects in the U87 cells, exhibits IC50 values of 34.2 and 28.4 µM, at 24 and 48 h, respectively[2]. Taraxerol acetate(10, 50 and 150 µM; 24 hours) induces cell apoptosis, the percentage of apoptotic cells increased from 7.3% in the control cells, to 16.1, 44.1 and in the 10, 50 and 150 µM taraxerol acetate-treated cells, respectively. Furthermore, taraxerol acetate treatment led to sub-G1 cell cycle arrest with a corresponding decrease in the number of S-phase cells[2].

[References]

[1]. Ubaid Ur Rehman1 A, et al. Molecular docking of taraxerol acetate as a new COX inhibitor. Journal of the Bangladesh Pharmacological Society

[2]. Hong JF, et al. Anticancer activity of taraxerol acetate in human glioblastoma cells and a mouse xenograft model via induction of autophagy and apoptotic cell death, cell cycle arrest and inhibition of cell migration.Mol Med Rep. 2016 Jun;13(6):4541-8.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
505.1±49.0 °C at 760 mmHg

[ Melting Point ]:
303-305ºC

[ Molecular Formula ]:
C32H52O2

[ Molecular Weight ]:
468.754

[ Flash Point ]:
256.2±17.4 °C

[ Exact Mass ]:
468.396729

[ PSA ]:
26.30000

[ LogP ]:
11.95

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.529

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds