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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

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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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
Biomedical properties of a natural dietary plant metabolite, zerumbone, in cancer therapy and chemoprevention trials
Rahman HS, et al.
BioMed Research International, 2014 (2014)
Remya Prasannan et al.
Biochemical pharmacology, 84(10), 1268-1276 (2012-07-31)
Phytochemicals and their synthetic derivatives are making a significant contribution in modern drug discovery programs by targeting several human diseases, including cancer. Most of these natural compounds are often multitargeted in nature, which is generally a very desirable property for
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)
Zerumbone from Zingiber zerumbet (L.) smith: a potential prophylactic and therapeutic agent against the cariogenic bacterium Streptococcus mutans
da Silva TM, et al.
BMC Complementary and Alternative Medicine, 18(1), 301-301 (2018)
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