9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

• ChemBase编号: 72641
• 分子式: C21H26O3
• 平均质量: 326.42934
• 单一同位素质量: 326.18819469
• SMILES: c1c(c(c(c(c1C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)C)C)OC
• Canonical SMILES: COc1cc(C)c(c(c1C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
• InChI: InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+
• InChIKey: IHUNBGSDBOWDMA-AQFIFDHZSA-N

名称和登记号

名称

• IUPAC标准名: 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid; (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• IUPAC传统名: acitretin; (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• 别名: 9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid; Acitretin; Soriatane; Acitretin; (all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid; Neotigason, Soriatane; Neotigason; Etretin

登记号

• CAS号: 55079-83-9
• EC号: 259-474-4
• MDL号: MFCD00866632
• PubChem SID: 24868318; 162037566
• PubChem CID: 5284513

理论计算性质

• Acid pKa: 5.011076
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 4.976502
• LogD (pH = 7.4): 3.2266924
• Log P: 5.5870485
• 摩尔折射率: 104.1665 cm^3
• 极化性: 38.030373 Å^3
• 极化表面积: 46.53 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform; DMSO; Methanol
• 外观: Yellow Solid
• 熔点: 215-218°C (dec.)

安全信息

• 保存条件: -20°C; Amber Vial, -20°C Freezer, Under Inert Atmosphere
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 有毒(Toxic) (T)
• 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: 61-36/38-50/53
• 安全公开号: 53-26-45-60-61
• GHS危险品标识: GHS07; GHS08; GHS09
• GHS警示词: Danger
• GHS危险声明: H315-H319-H360-H410
• GHS警示性声明: P201-P273-P305 + P351 + P338-P308 + P313-P501
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3077 9/PG 3

药理学性质

• 生物活性机理: Second generation retinoid

产品相关信息

• 纯度: ≥98.0% (HPLC)
• 成盐信息: Free Base
• 应用领域: Active against epithelial tumours; Used for treatment of psoriasis, antineoplastic agent
• Empirical Formula (Hill Notation): C21H26O3

详细说明

Selleck Chemicals - S1368

Research Area: Inflammation
Biological Activity:
Acitretin is a second generation retinoid. It is taken orally, and is typically used for psoriasis. It is a metabolite of etretinate, which was used prior to the introduction of acitretin. Etretinate was discontinued because it had a narrow therapeutic index as well as a long elimination half-life (t1/2=120 days), making dosing difficult. In contrast, acitretin’s half-life is approximately 2 days. [1]

Sigma Aldrich - 44707

Biochem/physiol Actions
Synthetic retinoid that is a metabolite of etretinate. Preferentially binds to cellular retinoic acid binding proteins (CRABPs).

Toronto Research Chemicals - A189900

A synthetic retinoid which is the major metabolite of etretinate (E938000).

参考文献

• http://en.wikipedia.org/wiki/Acitretin
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