Taraxerol

Names

[ CAS No. ]:
127-22-0

[ Name ]:
Taraxerol

[Synonym ]:
UNII-A32778O852
D-Friedoolean-14-en-3beta-ol
Isoolean-14-en-3b-ol
alnulin
(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-picenol
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-, (3S,4aR,6aR,8aR,12aR,12bS,14aR,14bR)-
Skimmiol
D-friedoolean-14-en-3β-ol
Taraxerol
Tiliadin
(3S,4aR,6aR,6aS,8aR,12aR,14aR,14bR)-4,4,6a,6a,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,12a,13,14,14a-tetradecahydropicen-3-ol
D-Friedoolean-14-en-3b-ol

Biological Activity

[Description]:

Taraxerol is isolated from Abroma augusta L, and has anti-inflammtory and anti-cancer effects. Taraxerol attenuates acute inlammation through inhibition of NF-κB signaling pathway. Taraxerol induces cell apoptosis[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[Target]

IC50: apoptosis[1]

[In Vitro]

Taraxerol (0-100 μM; 24 or 48 hours)significantly reduces cell viability to 95% (20 μM), 89.8% (40 μM), 82.6 % (60 μM), 72.9 % (80 μM), and 63.6% (100 μM).And this compound has cell viability of 90.7% at a concentration of 20 μM and 53.6% at the 100 μM concentration at 48 hours in Hela cells[1]. Taraxerol (80 μM; 24 or 48 hours) induces Hela cells apoptosis and cell death in a dose-dependent manner.Taraxerol can induce a significant apoptosis of cells by annexin V/ PI double staining, significant increase in both the early (24.2%) and late (16.2%) stages of apoptotic cells compared with the control group at the early (6.5%) and late (0.5%) stages[1].

[In Vivo]

Taraxerol (5 and 10mg/kg; i.p.) attenuates carrageenan induced paw edema 2h onward. The effect of taraxerol at the dose of 5mg/kg is found to be significant (p<0.05) only after 4h of carrageenan treatment[2].

[References]

[1]. Yaoi X, et al. Taraxerol Induces Cell Apoptosis through A Mitochondria-Mediated Pathway in HeLa Cells.Cell J. 2017 Oct;19(3):512-519.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
490.7±44.0 °C at 760 mmHg

[ Melting Point ]:
282-285°

[ Molecular Formula ]:
C₃₀H₅₀O

[ Molecular Weight ]:
426.717

[ Flash Point ]:
217.7±20.7 °C

[ Exact Mass ]:
426.386169

[ PSA ]:
20.23000

[ LogP ]:
11.06

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.539

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Precursor & DownStream

Precursor

DownStream

Articles

A new taraxerol derivative from the roots of Microcos tomentosa.

Nat. Prod. Commun. 8(10) , 1371-2, (2013)

A new 3beta-O-vanilloyl-taraxerol, microcisin (1) and eight known compounds, 3beta-taraxerol acetate (2), 3beta-taraxerol (3), cholest-4-en-3-one (4), cholest-4-en-6beta-ol-3-one (5), beta-sitosterol ...

[Chemical constituents in the leave of Rhizophora stylosa L and their biological activities].

Yao Xue Xue Bao 43(9) , 974-8, (2008)

Ten compounds were isolated from the leaves of Rhizophora stylosa, one kind of mangrove plants distributed in the tropical and subtropical areas of the world. Their structures were identified as tarax...

Taraxerol inhibits LPS-induced inflammatory responses through suppression of TAK1 and Akt activation.

Int. Immunopharmacol. 15(2) , 316-24, (2013)

Taraxerol, a triterpenoid compound, has potent anti-inflammatory effects. However, the molecular mechanisms are not clear. In the study, taraxerol concentration dependently inhibited nitric-oxide synt...