1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one

• ChemBase编号: 154822
• 分子式: C16H14O4
• 平均质量: 270.27996
• 单一同位素质量: 270.08920893
• SMILES: COc1cc(cc(c1C(=O)/C=C/c1ccccc1)O)O
• Canonical SMILES: COc1cc(O)cc(c1C(=O)/C=C/c1ccccc1)O
• InChI: InChI=1S/C16H14O4/c1-20-15-10-12(17)9-14(19)16(15)13(18)8-7-11-5-3-2-4-6-11/h2-10,17,19H,1H3
• InChIKey: NYSZJNUIVUBQMM-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one; (2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one
• IUPAC传统名: cardamomin; cardamonin
• 别名: (2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-phenyl-2-propen-1-one; (8CI); Alpinetin chalcone; (E)-2′,4′-Dihydroxy-6′-methoxy-chalcone; Cardamonin; 2',4'-Dihydroxy-6'-methoxychalcone

登记号

• CAS号: 19309-14-9
• MDL号: MFCD00238554
• PubChem SID: 162248960
• PubChem CID: 641785

理论计算性质

• Acid pKa: 7.1982746
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 3.7669728
• LogD (pH = 7.4): 3.3569512
• Log P: 3.7755234
• 摩尔折射率: 77.302 cm^3
• 极化性: 29.05835 Å^3
• 极化表面积: 66.76 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: ≥20 mg/mL
• 外观: Orange powder; yellow 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
• 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: 61
• GHS危险品标识: GHS09
• GHS警示词: Warning
• GHS危险声明: H400
• GHS警示性声明: P273
• RID/ADR: UN 3077 9/PG 3
• 保存温度: room temp

产品相关信息

• 纯度: ≥98% (HPLC); 99.0
• Empirical Formula (Hill Notation): C16 H14 O4

详细说明

Sigma Aldrich - C8249

Biochem/physiol Actions
Cardamonin is a calchone from Aplinia species (zingiberaceous plant species). Cardamonin inhibits pigmentation in melanocytes through suppression of Wnt/b-catenin signaling pathway. Cardamonin suppressed Wnt/b-catenin signaling by a mechanism involving proteasome-mediated degradation of b-catenin (GSK-3b-independent pathway). Research has shown that Cardamonin possesses anti-inflammatory activity via suppression of NF-kB nuclear translocation and Ik-Ba phosphorylation.