(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编号: 73026
• 分子式: C15H24O2
• 平均质量: 236.34986
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: (1S,2S,5S,8R,9S)-9-isopropyl-2-methyl-6-methylidene-11-oxatricyclo[6.2.1.0^{1,5}]undecan-8-ol
• 别名: Curcumol

登记号

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

理论计算性质

• Acid pKa: 11.751473
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.0727634
• LogD (pH = 7.4): 3.0727444
• Log P: 3.0727637
• 摩尔折射率: 67.9193 cm^3
• 极化性: 27.240015 Å^3
• 极化表面积: 29.46 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

安全信息

• 保存条件: -20°C

产品相关信息

• 成盐信息: Free Base

详细说明

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]

参考文献

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