Z3902

Zerumbone

≥98% (HPLC)

• Synonym(s): (2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one, Zerumbone (6CI,7CI)
• 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

Properties

• 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

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).

Safety Information

• Pictograms: 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