3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

• ChemBase编号: 127918
• 分子式: C16H12O7
• 平均质量: 316.26228
• 单一同位素质量: 316.05830272
• SMILES: COc1c(ccc(c1)c1c(c(=O)c2c(cc(cc2o1)O)O)O)O
• Canonical SMILES: COc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1O)O
• InChI: InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
• InChIKey: IZQSVPBOUDKVDZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
• IUPAC传统名: isorhamnetin
• 别名: 3′-Methoxy-3,4′,5,7-tetrahydroxyflavone; Isorhamnetin; 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one; 3,3',5,7-Tetrahydroxy-3'-methoxyflavone; 3'-Methylquercetin; C.I. 75680; Isorhamnetin; Quercetin 3'-Methyl Ether; 3'-O-Methyl Quercetin; 3-methylquercetin; Isorhamnetol; isorhamentin; isorhamnetine; iso-rhamnetin; 3'-Methoxyquercetin; Tamarixetin; Isorhamnetin

登记号

• CAS号: 480-19-3
• EC号: 207-545-5
• MDL号: MFCD00017310
• Beilstein号: 44723
• PubChem SID: 162222235; 24850701
• PubChem CID: 5281654
• CHEMBL: 379064
• 美国药典/FDA物质标识码: 73WRA8Z8M8
• 维基百科标题: Isorhamnetin

理论计算性质

• 摩尔折射率: 81.3445 cm^3
• 极化性: 30.311304 Å^3
• 极化表面积: 116.45 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true
• Acid pKa: 6.381414
• 质子受体: 7
• 质子供体: 4
• LogD (pH = 5.5): 2.2488089
• LogD (pH = 7.4): 1.1663433
• Log P: 2.3021934

分子性质

理化性质

• 外观: Yellow powder
• 熔点: 307 °C

安全信息

• RTECS编号: LK9275450
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 40
• 安全公开号: 36/37
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H351
• GHS警示性声明: P281
• 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
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95.0% (HPLC); ≥99% (HPLC)
• 级别: analytical standard
• 有效期: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C16H12O7

详细说明

Sigma Aldrich - 17794

Biochem/physiol Actions
Isorhamnetin inhibits adipogenesis by interfering with differentiation of adipose stem cells, by a mechanism involving stabilization of β-catenin and up-regulating the Wnt signaling pathway.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 17794.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Sigma Aldrich - 38907

Biochem/physiol Actions
Isorhamnetin inhibits adipogenesis by interfering with differentiation of adipose stem cells, by a mechanism involving stabilization of β-catenin and up-regulating the Wnt signaling pathway.1

Toronto Research Chemicals - M326575

A metabolite of the flavanoid Quercetin (Q509500) with antioxidant properties. It helps to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress via the modulation of PI3K/Akt and ERK1/2 signaling pathways.

参考文献

• Duenas, M. et al.: Eur. Food Res. Technol., 232, 103 (2011)
• Ameho, C.K. et al.: J. Nutrit. Biochem., 19, 467 (2011)
• Angeloni, C. et al.: Biochimie, 89, 73 (2011)