zerumbone

Names

[ CAS No. ]:
471-05-6

[ Name ]:
zerumbone

[Synonym ]:
(2E,6E,10E)-2,6,9,9-Tetramethyl-2,6,10-cycloundecatrien-1-one
(2E,6E,10E)-2,6,9,9-Tetramethylcycloundeca-2,6,10-trien-1-one
2,6,10-Cycloundecatrien-1-one, 2,6,9,9-tetramethyl-, (2E,6E,10E)-
ZERUMBONE ((2E,6E,10E)-2,6,9,9-TETRAMETHYLCYCLOUNDECA-2,6,10-TRIEN-1-ONE)
zerumbone

Biological Activity

[Description]:

Zerumbone is a monocyclic sesquiterpene compound isolated from the rhizomes of Zingiber zerumbet Smith. Zerumbone potently inhibits the activation of Epstein-Barr virus with an IC50 of 0.14 mM. Zerumbone has anti-cancer, antioxidant, anti-inflammatory and anti-proliferative activity[1][2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HSV

Research Areas >> Infection

[References]

[1]. Murakami A, et al. Identification of zerumbone in Zingiber zerumbet Smith as a potent inhibitor of 12-O-tetradecanoylphorbol-13-acetate-induced Epstein-Barr virus activation. Biosci Biotechnol Biochem. 1999 Oct;63(10):1811-2.

[2]. Kalantari K, et al. A Review of the Biomedical Applications of Zerumbone and the Techniques for Its Extractionfrom Ginger Rhizomes. Molecules. 2017 Sep 30;22(10).

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
321.6±42.0 °C at 760 mmHg

[ Melting Point ]:
67-69℃

[ Molecular Formula ]:
C₁₅H₂₂O

[ Molecular Weight ]:
218.335

[ Flash Point ]:
133.9±22.8 °C

[ Exact Mass ]:
218.167068

[ PSA ]:
17.07000

[ LogP ]:
5.34

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

[ Index of Refraction ]:
1.468

[ Storage condition ]:
2-8℃

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H317-H400

[ Precautionary Statements ]:
P273-P280

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
43-50

[ Safety Phrases ]:
36/37-60-61

[ RIDADR ]:
UN 3077 9 / PGIII

Articles

Zingiber zerumbet CYP71BA1 catalyzes the conversion of α-humulene to 8-hydroxy-α-humulene in zerumbone biosynthesis.

Cell. Mol. Life Sci. 68(6) , 1033-40, (2011)

Plant cytochrome P450s are involved in the biosynthesis of various classes of secondary metabolites. To elucidate the biosynthesis of zerumbone, a sesquiterpenoid with multiple potential anticancer pr...

Altered cross-linking of HSP27 by zerumbone as a novel strategy for overcoming HSP27-mediated radioresistance.

Int. J. Radiat. Oncol. Biol. Phys. 79(4) , 1196-205, (2011)

HSP27 or HSP25 negatively regulates apoptosis pathways after radiation or chemotherapeutic agents. Abrogation of HSP27 function may be a candidate target for overcoming radio- and chemoresistance.Zeru...

Effects of selected food phytochemicals in reducing the toxic actions of TCDD and p,p'-DDT in U937 macrophages.

Arch. Toxicol. 84(12) , 957-66, (2010)

To assess the effectiveness of selected food phytochemicals in reducing the toxic effects of the environmental toxicants, 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and p,p'-DDT (DDT), we tested the p...