Z3902
Zerumbone
≥98% (HPLC), TRAIL-induced apoptosis potentiator, powder
Synonym(s):
(2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one, Zerumbone (6CI,7CI)
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About This Item
Empirical Formula (Hill Notation):
C15H22O
CAS Number:
Molecular Weight:
218.33
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
Zerumbone, ≥98% (HPLC)
Quality Level
assay
≥98% (HPLC)
form
powder
color
white to off-white
solubility
DMSO: ≥10 mg/mL
storage temp.
2-8°C
SMILES string
C\C1=C/CC(C)(C)\C=C\C(=O)\C(C)=C\CC1
InChI
1S/C15H22O/c1-12-6-5-7-13(2)14(16)9-11-15(3,4)10-8-12/h7-9,11H,5-6,10H2,1-4H3/b11-9+,12-8+,13-7+
InChI key
GIHNTRQPEMKFKO-SKTNYSRSSA-N
General description
Zerumbone is a monocyclic sesquiterpene compound, which is extracted from the essential oil of Zingiber zerumbet rhizomes. It has antimicrobial, antinociceptive, antiatherosclerotic, hepatoprotective and antioxidant properties. Zerumbone also has anti-inflammatory and anticancer effects.
Application
Zerumbone has been used:
- for liquid chromatography with mass spectrometry (LC-MS-MS)
- to investigate its potential application in the prevention
- treatment of esophageal squamous cell carcinomas (ESCC)
Biochem/physiol Actions
TRAIL-induced apoptosis potentiator; DR4 and DR5 inducer
Zerumbone is a TRAIL-induced apoptosis potentiator. It potentiates TRAIL-induced apoptosis through the up-regulation of DR4 and DR5 expression and the down-regulation of cFLIP. Zerumbone has very little or no cytotoxic effect on the normal human endothelial cells and dermal fibroblasts. Zerumbone is a sesquiterpene isolated from in Zingiber zerumbet Smith (wild ginger).
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signalword
Warning
hcodes
Hazard Classifications
Aquatic Acute 1 - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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The ethanol extract of Zingiber zerumbet Smith attenuates non-alcoholic fatty liver disease in hamsters fed on high-fat diet
Chang CJ, et al.
Food And Chemical Toxicology, 65, 33-42 (2014)
Bo-Yie Chen et al.
Molecular vision, 17, 854-863 (2011-04-30)
Ultraviolet B (UVB) irradiation activates nuclear factor-kappa B (NF-κB) and inducible nitric oxide synthase (iNOS) in the cornea, resulting in inflammatory responses and malondialdehyde (MDA) accumulation. This study aims to determine the effect of zerumbone, a potent NF-κB inhibitor and
Eltayeb E M Eid et al.
Journal of mass spectrometry : JMS, 46(8), 772-781 (2011-08-13)
A rapid, sensitive, specific and selective LC-MS/MS method for the determination of zerumbone (ZER) in human plasma using 2,4-diamino-6-(4-methoxyphenyl)-1,3,5-triazine (DMTZ) as an internal standard (IS) has been developed and validated. ZER was chromatographed on C8 column using a mobile phase