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Z3902

Sigma-Aldrich

Zerumbone

≥98% (HPLC)

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
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

Signal Word

Warning

Hazard Statements

H317,H400

Precautionary Statements

P273 - P280 - P302 + P352

Hazard Classifications

Aquatic Acute 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Eltayeb E M Eid et al.
Journal of mass spectrometry : JMS, 46(8), 772-781 (2011-08-13)
A rapid, sensitive, specific and selective LC-MS/MS method for the determination of zerumbone (ZER) in human plasma using 2,4-diamino-6-(4-methoxyphenyl)-1,3,5-triazine (DMTZ) as an internal standard (IS) has been developed and validated. ZER was chromatographed on C8 column using a mobile phase
Anuradha Sehrawat et al.
Breast cancer research and treatment, 136(2), 429-441 (2012-10-12)
The present study was undertaken to determine the anticancer efficacy of zerumbone (ZER), a sesquiterpene from subtropical ginger, against human breast cancer cells in vitro and in vivo. ZER treatment caused a dose-dependent decrease in viability of MCF-7 and MDA-MB-231
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
John H Beattie et al.
Molecular nutrition & food research, 55 Suppl 2, S203-S213 (2011-10-05)
Natural dietary anti-obesogenic phytochemicals may help combat the rising global incidence of obesity. We aimed to identify key hepatic pathways targeted by anti-obsogenic ginger phytochemicals fed to mice. Weaning mice were fed a high-fat diet containing 6-gingerol (HFG), zerumbone (HFZ)
Zerumbone inhibits migration in ESCC via promoting Rac1 ubiquitination
Wang M, et al.
Biomedicine and Pharmacotherapy, 109, 2447-2455 (2019)
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