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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

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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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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