2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one

• ChemBase ID: 154624
• Molecular Formular: C15H22O
• Molecular Mass: 218.33458
• Monoisotopic Mass: 218.16706532
• SMILES: CC1=CCC(C=CC(=O)C(=CCC1)C)(C)C
• Canonical SMILES: CC1=CCC(C)(C)C=CC(=O)C(=CCC1)C
• InChI: 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
• InChIKey: GIHNTRQPEMKFKO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one
• IUPAC Traditional name: 2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one
• Synonyms: (2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one; Zerumbone (6CI,7CI); Zerumbone

Database IDs

• CAS Number: 471-05-6
• MDL Number: MFCD03700769
• PubChem SID: 162248762
• PubChem CID: 71311914

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.5707407
• LogD (pH = 7.4): 4.5707407
• Log P: 4.5707407
• Molar Refractivity: 72.2184 cm^3
• Polarizability: 27.021826 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 43-50
• Safety Statements: 36/37-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H400
• GHS Precautionary statements: P273-P280
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H22O

DETAILS

Sigma Aldrich - Z3902

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).