4-[(2R,3S)-3-[(3,4-dimethoxyphenyl)methyl]-2-methylbutyl]-1,2-dimethoxybenzene

• ChemBase编号: 153218
• 分子式: C22H30O4
• 平均质量: 358.4712
• 单一同位素质量: 358.21440944
• SMILES: C[C@H](Cc1ccc(c(c1)OC)OC)[C@@H](C)Cc1ccc(c(c1)OC)OC
• Canonical SMILES: COc1cc(ccc1OC)C[C@H]([C@H](Cc1ccc(c(c1)OC)OC)C)C
• InChI: InChI=1S/C22H30O4/c1-15(11-17-7-9-19(23-3)21(13-17)25-5)16(2)12-18-8-10-20(24-4)22(14-18)26-6/h7-10,13-16H,11-12H2,1-6H3/t15-,16+
• InChIKey: ORQFDHFZSMXRLM-IYBDPMFKSA-N

名称和登记号

名称

• IUPAC标准名: 4-[(2R,3S)-3-[(3,4-dimethoxyphenyl)methyl]-2-methylbutyl]-1,2-dimethoxybenzene
• IUPAC传统名: 4-[(2R,3S)-3-[(3,4-dimethoxyphenyl)methyl]-2-methylbutyl]-1,2-dimethoxybenzene
• 别名: 2,3-Dimethyl-1,4-bis-(3,4-dimethoxyphenyl)butane; EM-1421; M4N; TMNDGA; Tetra-O-methyl nordihydroguaiaretic acid; rel-4-[(2R,3S)-4-(3,4-Dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene; tetra-O-methyl-NDGA; tetramethyl NDGA; tetramethyl Nordihydroguaiaretic Acid; Terameprocol

登记号

• CAS号: 24150-24-1
• MDL号: MFCD11113155
• PubChem SID: 162247357
• PubChem CID: 476861

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 5.342099
• LogD (pH = 7.4): 5.342099
• Log P: 5.342099
• 摩尔折射率: 104.5482 cm^3
• 极化性: 40.89223 Å^3
• 极化表面积: 36.92 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: ≥10 mg/mL
• 外观: white to off-white powder

安全信息

• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N)
• 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: 50/53
• 安全公开号: 60-61
• GHS危险品标识: GHS09
• GHS警示词: Warning
• GHS危险声明: H410
• GHS警示性声明: P273-P501
• RID/ADR: UN 3077 9/PG 3
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H30O4

详细说明

Sigma Aldrich - T3455

Biochem/physiol Actions
Terameprocol is a synthetic derivative of NDGA, a non-selective lipoxygenase inhibitor. It inhibits Sp1 transcription factor binding at the HIV long terminal repeat promoter and at the α-ICP4 promoter, a gene essential for HSV replication, with IC50 values of 11 and 43.5 μM respectively. TMNDGA induces growth arrest and apoptosis by suppressing Sp1-dependent Cdc2 and survivin gene expression giving rise to its antitumorigenic activity. The in vivo growth of xenografts in numerous human tumor types was suppressed upon treatment with TMNDGA It also inhibits the growth of murine and human melanomas and human colon cancer in vivo without causing other tissue toxicity.