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Z3902

Sigma-Aldrich

Zerumbone

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C15H22O
Numéro CAS:
Poids moléculaire :
218.33
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Niveau de qualité

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to off-white

Solubilité

DMSO: ≥10 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

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+

Clé InChI

GIHNTRQPEMKFKO-SKTNYSRSSA-N

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Description générale

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)

Actions biochimiques/physiologiques

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).

Pictogrammes

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Mention d'avertissement

Warning

Mentions de danger

Conseils de prudence

Classification des risques

Aquatic Acute 1 - Skin Sens. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


Certificats d'analyse (COA)

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Les clients ont également consulté

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Zerumbone inhibits migration in ESCC via promoting Rac1 ubiquitination
Wang M, et al.
Biomedicine and Pharmacotherapy, 109, 2447-2455 (2019)
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
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
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)

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