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Z3902

Sigma-Aldrich

Zerumbone

≥98% (HPLC)

Sinónimos:

(2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one, Zerumbone (6CI,7CI)

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About This Item

Fórmula empírica (notación de Hill):
C15H22O
Número de CAS:
471-05-6
Peso molecular:
218.33
MDL number:
MFCD03700769
UNSPSC Code:
12352200
PubChem Substance ID:
329831611
NACRES:
NA.77

Quality Level

100

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

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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

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).

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H317,H400

Hazard Classifications

Aquatic Acute 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
Zerumbone inhibits migration in ESCC via promoting Rac1 ubiquitination
Wang M, et al.
Biomedicine and Pharmacotherapy, 109, 2447-2455 (2019)
John H Beattie et al.
Molecular nutrition & food research, 55 Suppl 2, S203-S213 (2011-10-05)
Natural dietary anti-obesogenic phytochemicals may help combat the rising global incidence of obesity. We aimed to identify key hepatic pathways targeted by anti-obsogenic ginger phytochemicals fed to mice. Weaning mice were fed a high-fat diet containing 6-gingerol (HFG), zerumbone (HFZ)
Anuradha Sehrawat et al.
Breast cancer research and treatment, 136(2), 429-441 (2012-10-12)
The present study was undertaken to determine the anticancer efficacy of zerumbone (ZER), a sesquiterpene from subtropical ginger, against human breast cancer cells in vitro and in vivo. ZER treatment caused a dose-dependent decrease in viability of MCF-7 and MDA-MB-231
Siddig Ibrahim Abdelwahab et al.
International immunopharmacology, 12(4), 594-602 (2012-02-15)
Interleukin-6 is one of the factors affecting sensitivity to cytotoxic agents. Therefore, the current study was designed to investigate the role of IL-6 and IL6 receptors in the cytotoxic effects of zerumbone in ovarian and cervical cancer cell lines (Caov-3
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