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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:
471-05-6
Poids moléculaire :
218.33
Numéro MDL:
MFCD03700769
Code UNSPSC :
12352200
ID de substance PubChem :
329831611
Nomenclature NACRES :
NA.77

Niveau de qualité

100

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

Exclamation markEnvironment
GHS07,GHS09

Mention d'avertissement

Warning

Mentions de danger

H317,H400

Conseils de prudence

P273 - P280 - P302 + P352

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)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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
Sho Okamoto et al.
The FEBS journal, 278(16), 2892-2900 (2011-06-15)
The rhizome oil of Zingiber zerumbet Smith contains an exceptionally high content of sesquiterpenoids with zerumbone, a predominating potential multi-anticancer agent. Biosynthetic pathways of zerumbone have been proposed, and two genes ZSS1 and CYP71BA1 that encode the enzymes catalyzing the
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
Behnam Kamalidehghan et al.
Iranian biomedical journal, 16(4), 226-226 (2012-11-28)
Zerumbone is a cytotoxic compound isolated from the herbal plant, Zingiber zerumbet Smith, which exhibits antitumor activity [1-2], anti-inflammatory effects and possesses anti-proliferative potentials in a variety of cell lines [3-4]. DNA fragmentation indicates an early event of apoptosis leading
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