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8-Shogaol

Names

[ CAS No. ]:
36700-45-5

[ Name ]:
8-Shogaol

[Synonym ]:
4-Dodecen-3-one, 1-(4-hydroxy-3-methoxyphenyl)-, (4E)-
(4E)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
8-Shogaol
(4E)-1-(4-Hydroxy-3-methoxyphenyl)-4-dodecen-3-one

Biological Activity

[Description]:

[8]-Shogaol, one of the pungent phenolic compounds in ginger, exhibits anti-platelet activity (IC50=5 μM) and inhibits COX-2 (IC50=17.5 μM). [8]-Shogaol induces apoptosis in human leukemia cells[1][2][3][4].

[Related Catalog]:

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

[Target]

COX-2:17.5 μM (IC50)


[References]

[1]. Shieh PC, et al. Induction of apoptosis by [8]-shogaol via reactive oxygen species generation, glutathione depletion, and caspase activation in human leukemia cells. J Agric Food Chem. 2010 Mar 24;58(6):3847-54.

[2]. van Breemen RB, et al. Cyclooxygenase-2 inhibitors in ginger (Zingiber officinale). Fitoterapia. 2011 Jan;82(1):38-43.

[3]. Nurtjahja-Tjendraputra E, et al. Effective anti-platelet and COX-1 enzyme inhibitors from pungent constituents of ginger. Thromb Res. 2003;111(4-5):259-65.

[4]. Shieh PC, et al. Induction of apoptosis by [8]-shogaol via reactive oxygen species generation, glutathione depletion, and caspase activation in human leukemia cells. J Agric Food Chem. 2010 Mar 24;58(6):3847-54.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
452.3±35.0 °C at 760 mmHg

[ Molecular Formula ]:
C19H28O3

[ Molecular Weight ]:
304.424

[ Flash Point ]:
154.6±19.4 °C

[ Exact Mass ]:
304.203857

[ PSA ]:
46.53000

[ LogP ]:
4.91

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.516

Related Compounds