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Z3902

Zerumbone

Name: Zerumbone
Brand: SIGMA

≥98% (HPLC), TRAIL-induced apoptosis potentiator, powder

Synonym(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

Empirical Formula (Hill Notation):

C₁₅H₂₂O

CAS Number:

471-05-6

Molecular Weight:

218.33

UNSPSC Code:

12352200

PubChem Substance ID:

329831611

NACRES:

NA.77

MDL number:

MFCD03700769

Assay:

≥98% (HPLC)

Form:

powder

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Properties

Product Name

Zerumbone, ≥98% (HPLC)

Quality Segment

100

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

Description

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

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).

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Pictograms

GHS07,GHS09

Signal Word

Warning

Hazard Codes

H317,H400

Precautionary Statements

P273 - P280 - P302 + P352

Hazard Classifications

Aquatic Acute 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)