2-(2,4-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one

• ChemBase编号: 154635
• 分子式: C18H16O5
• 平均质量: 312.31664
• 单一同位素质量: 312.09977361
• SMILES: COc1ccc2c(c1)c(=O)cc(o2)c1ccc(cc1OC)OC
• Canonical SMILES: COc1ccc(c(c1)OC)c1cc(=O)c2c(o1)ccc(c2)OC
• InChI: InChI=1S/C18H16O5/c1-20-11-5-7-16-14(8-11)15(19)10-18(23-16)13-6-4-12(21-2)9-17(13)22-3/h4-10H,1-3H3
• InChIKey: WUWFDVDASNSUKP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(2,4-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one
• IUPAC传统名: 2-(2,4-dimethoxyphenyl)-6-methoxychromen-4-one
• 别名: 2-(2,4-Dimethoxyphenyl)-2,3-dihydro-6-methoxy-4H-1-benzopyran-4-one; TMF; Trimethoxyflavone; 6, 2′, 4′-trimethoxyflavone

登记号

• CAS号: 720675-90-1
• MDL号: MFCD03412381
• PubChem SID: 162248773
• PubChem CID: 688802

理论计算性质

• Acid pKa: 15.155552
• 质子受体: 5
• 质子供体: 0
• LogD (pH = 5.5): 2.4943714
• LogD (pH = 7.4): 2.4943712
• Log P: 2.4943714
• 摩尔折射率: 86.3608 cm^3
• 极化性: 32.825787 Å^3
• 极化表面积: 53.99 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >5 mg/mL
• 外观: yellow powder

安全信息

• 保存条件: desiccated; protect from light
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 25
• 安全公开号: 45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: room temp

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H16O5

详细说明

Sigma Aldrich - T4080

Biochem/physiol Actions
6, 2′, 4′-trimethoxyflavone is a selective aryl hydrocarbon receptor (AHR) antagonist with no partial agonist activity. The role of the transcription factor aryl hydrocarbon receptor (AHR) in biology is still under evaluation and has expanded beyond that of a xenobiotic sensor and regulator of detoxification. Inhibition of AHR activity by antagonists could result in anti-inflammatory actions. 6, 2′, 4′-trimethoxyflavone (TMF) is a pure AHR antagonist. The compound compete with agonists, such as 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD) and benzo[a]pyrene (B[a]P), thus effectively inhibiting AHRmediated transactivation of a heterologous reporter and endogenous targets e.g. CYP1A1. TMF also exhibits no species or promoter dependency with regard to AHR antagonism. Thus it represents an improved tool allowing for more precise dissection of AHR function.