(1R,4aR,4bR,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid

• ChemBase编号: 107695
• 分子式: C20H30O2
• 平均质量: 302.451
• 单一同位素质量: 302.2245802
• SMILES: CC(C)C1=CC2=CC[C@@H]3[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1
• Canonical SMILES: CC(C1=CC2=CC[C@@H]3[C@]([C@H]2CC1)(C)CCC[C@@]3(C)C(=O)O)C
• InChI: InChI=1S/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1
• InChIKey: RSWGJHLUYNHPMX-ONCXSQPRSA-N

名称和登记号

名称

• IUPAC标准名: (1R,4aR,4bR,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid
• IUPAC传统名: abietic acid
• 别名: 松香酸; (1R,4aR,4bR,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid; Abietinic acid; Sylvic acid; Abietic acid; (1R,4aR,4bR,10aR)-1,2,3,4,4a,4b,5,6,10,10a-Decahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylic Acid; 13-Isopropylpodocarpa-7,13-dien-15-oic Acid; (-)-Abietic Acid; 7,13-Abietadien-18-oic Acid; Abietic Acid; NSC 25149; Odomit B 10; ZAO; l-Abietic Acid; Abietic Acid, 75%; Abietic acid; ABIETIC ACID PRACTICAL GRADE

登记号

• CAS号: 514-10-3
• EC号: 208-178-3; 208-173-3
• MDL号: MFCD03423567
• Beilstein号: 2221451
• PubChem SID: 24891449; 24844957; 162093761
• PubChem CID: 10569
• CHEBI ID: 28987
• CHEMBL: 71893
• Chemspider ID: 10127
• KEGG ID: C06087
• 美国药典/FDA物质标识码: V3DHX33184
• 维基百科标题: Abietic_acid

理论计算性质

• Acid pKa: 4.589813
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.9930508
• LogD (pH = 7.4): 2.2175677
• Log P: 4.952565
• 摩尔折射率: 91.2142 cm^3
• 极化性: 35.413227 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Very soluble in acetone, petroleum ether, Et₂O, and ethanol.
• 外观: Powder; yellow resinous powder, crystals or chunks. Monoclinic plates (from EtOH/water).
• 熔点: ~155 °C; 139-142 °C(lit.); 139-142°C; 140°C
• 沸点: 439.5°C
• 密度: 1.06 g/mL
• 比旋光度: [α]20/D -85±10°, c = 1% in ethanol

安全信息

• RTECS编号: TP8580000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 3077
• 德国WGK号: 3
• 联合国危险货物等级: 9
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 36/37/38-50/53; R36/37/38
• 安全公开号: 26-36; S26 S36
• GHS危险品标识: GHS07; GHS09
• GHS警示词: Warning
• 主要危害: Irritant, Not Good For Nature
• NFPA704:
  

  0

  1

  0
• GHS危险声明: H315-H319-H335-H400
• GHS警示性声明: P261-P273-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... TNF(7124)

产品相关信息

• 纯度: ~75% (GC); ≥65% (GC); 93.0
• 级别: PRACTICAL; technical
• Empirical Formula (Hill Notation): C20H30O2

详细说明

MP Biomedicals - 05204616

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 00010

Other Notes
天然产物合成的原料1,2,3；可与 MCPBA 发生环氧化作用4

Toronto Research Chemicals - A108200

Abietic Acid is the primary component of resin acid found commonly in rosin. Abietic Acid exhibited potent testosterone 5α-reductase inhibitory activity in vitro.

参考文献

• Roh, S.-S. et al.: J. Health Sci., 56, 451 (2010)
• Harris, G.C. et al.: Org. Synth., 32, 1 (2010)