(1S,2S,5S,8R,9S)-2-methyl-6-methylidene-9-(propan-2-yl)-11-oxatricyclo[6.2.1.0^{1,5}]undecan-8-ol

• ChemBase ID: 73026
• Molecular Formular: C15H24O2
• Molecular Mass: 236.34986
• Monoisotopic Mass: 236.17763001
• SMILES: C1(=C)[C@H]2[C@]3(C[C@H]([C@](C1)(O)O3)C(C)C)[C@H](CC2)C
• Canonical SMILES: CC([C@@H]1C[C@]23O[C@]1(O)CC(=C)[C@@H]3CC[C@@H]2C)C
• InChI: InChI=1S/C15H24O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h9,11-13,16H,3,5-8H2,1-2,4H3/t11-,12-,13-,14-,15+/m0/s1
• InChIKey: QRMPRVXWPCLVNI-YYFQZIEXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5S,8R,9S)-2-methyl-6-methylidene-9-(propan-2-yl)-11-oxatricyclo[6.2.1.0^{1,5}]undecan-8-ol
• IUPAC Traditional name: (1S,2S,5S,8R,9S)-9-isopropyl-2-methyl-6-methylidene-11-oxatricyclo[6.2.1.0^{1,5}]undecan-8-ol
• Synonyms: Curcumol

Database IDs

• CAS Number: 4871-97-0
• PubChem SID: 162037946
• PubChem CID: 14240392

CALCULATED PROPERTIES

• Acid pKa: 11.751473
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.0727634
• LogD (pH = 7.4): 3.0727444
• Log P: 3.0727637
• Molar Refractivity: 67.9193 cm^3
• Polarizability: 27.240015 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2407

Research Area: Metabolic Disease
Biological Activity:
Curcumol is a common traditional Chinese medicine with antitumor activities. Curcumol is isolated from Rhizoma Curcumae. Curcumol is one of the major components of the essential oil of Curcuma wenyujin with the structure of a guaiane-type sesquiterpenoid hemiketal. Curcumol exhibits clear antitumor, antihepatic fibrosis, antioxidant, and antimicrobial activities. Curcumol is one of the representative index components in the quality standard of the essential oil which is currently used as an anti-cancer and anti-virus remedy,and embodied in the Pharmacopoeia of the P.R.China(2005). Curcumol induced a rapid translocation of Bax from cytosol into mitochondria within 6 h, leading to a rapid dissipation of mitochondrial membrane potential (?Ψm), implying that mitochondria play an important role in the curcumol-induced apoptosis. The fact that Z-VAD-fmk, a broad-spectrum inhibitor of caspases, did not reduce the curcumol-induced apoptosis showed that caspases were not involved in curcumol-induced apoptosis, which was further verified by monitoring the caspase-3 activation inside living cells stably expressing SCAT3, a FRET plasmid. curcumol induced cell death in a dominant apoptotic fashion via the caspases-independent mitochondrial pathway in ASTC-a-1 cells. [1][2][3]

REFERENCES

• Zhang W et al. Med Oncol. 2011 Mar; 28(1):307-14.