(3R,4R,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid

• ChemBase编号: 162702
• 分子式: C30H48O3
• 平均质量: 456.70032
• 单一同位素质量: 456.3603454
• SMILES: C1C[C@H]([C@](C2[C@]1([C@@H]1[C@@](CC2)([C@]2(C(=CC1)[C@H]1[C@@](CC2)(CC[C@H]([C@@H]1C)C)C)C)C)C)(C)C(=O)O)O
• Canonical SMILES: C[C@@H]1CC[C@]2([C@@H]([C@H]1C)C1=CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CCC1[C@]3(C)CC[C@H]([C@]1(C)C(=O)O)O)C
• InChI: InChI=1S/C30H48O3/c1-18-10-13-26(3)16-17-28(5)20(24(26)19(18)2)8-9-21-27(4)14-12-23(31)30(7,25(32)33)22(27)11-15-29(21,28)6/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21-,22?,23-,24+,26-,27-,28-,29-,30-/m1/s1
• InChIKey: NBGQZFQREPIKMG-AKOQEMLPSA-N

名称和登记号

名称

• IUPAC标准名: (3R,4R,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid
• IUPAC传统名: (3R,4R,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-4-carboxylic acid
• 别名: (3α,4β)-3-Hydroxyurs-12-en-23-oic Acid; β-Boswellic Acid

登记号

• CAS号: 631-69-6
• PubChem SID: 162256837
• PubChem CID: 46783539

理论计算性质

• Acid pKa: 4.5676003
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 5.6025105
• LogD (pH = 7.4): 3.8282661
• Log P: 6.581805
• 摩尔折射率: 133.698 cm^3
• 极化性: 53.23124 Å^3
• 极化表面积: 57.53 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform; Ethyl Acetate; Methanol
• 外观: Off-White Solid
• 熔点: 220-223°C

安全信息

• 保存条件: -20°C Freezer

详细说明

Toronto Research Chemicals - B676500

The principal constitutents of frankincense (olibanum). A specific, nonredox inhibitor of 5-lipoxygenase used to treat inflammation.

参考文献

• Zhang, Y., et al.: Bioorg. Med. Chem., 16, 8697 (2008)
• Siemoneit, U., et al.: Eur. J. Pharmacol., 606, 246 (2008)