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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
Número MDL:
MFCD03700769
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
329831611
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

color

white to off-white

solubilidad

DMSO: ≥10 mg/mL

temp. de almacenamiento

2-8°C

cadena 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+

Clave InChI

GIHNTRQPEMKFKO-SKTNYSRSSA-N

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Descripción general

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.

Aplicación

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)

Acciones bioquímicas o fisiológicas

TRAIL-induced apoptosis potentiator; DR4 and DR5 inducer
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).

Pictogramas

Exclamation markEnvironment
GHS07,GHS09

Palabra de señalización

Warning

Frases de peligro

H317,H400

Consejos de prudencia

P273 - P280 - P302 + P352

Clasificaciones de peligro

Aquatic Acute 1 - Skin Sens. 1

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
096M4768V
026M4703V
113M4738V
013M4719V
010M47241

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Sigma-Aldrich

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Quercetin ≥95% (HPLC), solid

Sigma-Aldrich

Q4951

Quercetin

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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