CAS Number480-19-3
Synonyms3 4' 5 7-tetrahydroxy-3'-methoxy flavone; MFCD00017310; 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one; isorhamnetine; 3,4',5,7-tetrahydroxy-3'-methoxyflavone; EINECS 207-545-5; 3-methylquercetin; 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one; quercetin-3'-methyl ether; ISOHAMNETIN; 3'-O-Methyl Quercetin; Isorhanetin; Isorhamnetin; 3'-methylquercetin; iso-rhamnetin; 3'-Methoxy-3,4',5,7-tetrahydroxyflavone; Isorhamnetol; 3'-methoxykaempferol
Molecular FormulaC16H12O7
Molecular Weight316.26
Purity≥95.0 (HPLC)%
Density1.6±0.1 g/cm3
Boiling Point599.4±50.0 °C at 760 mmHg
Melting Point307°C
AppearanceSolid;Light yellow to Amber to Dark green powder to crystal
EINECS207-545-5
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 480-19-3 |
| Catalog No. | 2A-9011058 |
| Chinese Name | 异鼠李素 |
| Synonyms | 3 4' 5 7-tetrahydroxy-3'-methoxy flavone; MFCD00017310; 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one; isorhamnetine; 3,4',5,7-tetrahydroxy-3'-methoxyflavone; EINECS 207-545-5; 3-methylquercetin; 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one; quercetin-3'-methyl ether; ISOHAMNETIN; 3'-O-Methyl Quercetin; Isorhanetin; Isorhamnetin; 3'-methylquercetin; iso-rhamnetin; 3'-Methoxy-3,4',5,7-tetrahydroxyflavone; Isorhamnetol; 3'-methoxykaempferol |
| Molecular Formula | C16H12O7 |
| Molecular Weight | 316.26 |
| Purity | ≥95.0 (HPLC) |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 599.4±50.0 °C at 760 mmHg |
| Melting Point | 307°C |
| Appearance | Solid;Light yellow to Amber to Dark green powder to crystal |
| Storage Condition | Sealed and stored in a cool, dry warehouse. |
| Application | Isorhamnetin is a flavonoid compound extracted from the Chinese herb sea buckthorn (Hippophae rhamnoides L.). Isorhamnetin inhibits skin cancer by directly inhibiting MEK1 and PI3K. |
| EINECS | 207-545-5 |
| PubChem ID | 57647674 |
| MDL Number | MFCD00017310 |
| SMILES | COc1cc(ccc1O)C2=C(O)C(=O)c3c(O)cc(O)cc3O2 |
| 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 |
| InChI Key | IZQSVPBOUDKVDZ-UHFFFAOYSA-N |
| Beilstein/REAXYS | 44723 |
| NACRES Code | NA.47 |
| UNSPSC | 12352205 |
| Hazard Symbols | Transport |
| MSDS | msds/11058_1_480_19_3.pdf |
| Bioactivity | Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K. Related Catalog Signaling Pathways >> MAPK/ERK Pathway >> MEK Research Areas >> Cardiovascular Disease Research Areas >> Cancer Natural Products >> Flavonoids Research Areas >> Inflammation/Immunology Target MEK1 PI3-K In Vitro Isorhamnetin is a plant flavonoid that occurs in fruits and medicinal herbs. Isorhamnetin binds directly to MEK1 in an ATP-noncompetitive manner and to PI3-K in an ATP-competitive manner. In vitro and ex vivo kinase assay data show that Isorhamnetin inhibits the kinase activity of MAP/ERK kinase (MEK) 1 and PI3-K and the inhibition is due to direct binding with Isorhamnetin[1]. Isorhamnetin inhibits the Akt/mTOR and MEK/ERK signaling pathways, and promotes the activity of the mitochondrial apoptosis signaling pathway. The inhibitory effects of Isorhamnetin on breast cancer cells are determined using the CCK-8 method. Isorhamnetin inhibits the proliferation of numerous breast cancer cells (IC50, ~10 µM), including MCF7, T47D, BT474, BT-549, MDA-MB-231 and MDA-MB-468, whereas less inhibitory activity is observed in the MCF10A normal breast epithelial cell line (IC50, 38 µM)[2]. In Vivo Photographic data shows that Isorhamnetin treatment suppresses tumor development in mice. The average volume of tumors in untreated mice increases over time and reaches a volume of 623 mm3 at 4 weeks post-inoculation; however, at this time, in mice treated with 1 or 5 mg/kg Isorhamnetin, the average tumor volume is only 280 or 198 mm3, respectively. At the end of the study, Isorhamnetin treatment (1 or 5 mg/kg) reduces tumor weight compared with the untreated control group[1]. Cell Assay MCF7, T47D, BT474, BT-549, MDA-MB-231 and MDA-MB-468 breast cancer cell lines, as well as a MCF10A normal breast epithelial cell line (control) are seeded into 96-well plates at a density of 5×103 cells/well in 100 µL DMEM and placed in cell incubator for 12 h at 37°C in an atmosphere containing 5% CO2. The cells are then treated with various concentrations of Isorhamnetin (100, 33.3, 11.1, 3.7, 1.2, 0.4 and 0 µM) for 48 h, and cell proliferation rates are determined by adding 10 µL CCK-8 solution prior to incubation at 37°C for 2 h. The absorbance is measured at a wavelength of 450 nm using a SpectraMax 190 Microplate Reader. For each assay, four parallel wells are included, and the half maximal inhibitory concentration (IC50) is measured using the inhibition curve and presented as the mean of three independent experiments[2]. Animal Admin Mice[1] Female athymic nude mice are injected subcutaneously in the flank with A431 cells (1×106 cells in 50 μL of medium and 50 μL of Matrigel). Cells are allowed to form tumors, and once the tumors reach a size of 40 mm3, the mice are randomly assigned into groups (6 mice/group) and treated with (1 or 5 mg/kg body weight) or without Isorhamnetin in 40% DMSO/PBS buffer, administered intraperitoneally every other day for 28 days. Tumor size is measured every week with calipers, and the tumor volume is calculated. Mice are sacrificed after 28 days of treatment when the control tumors reach approximately 600 mm3. The tumors are harvested, photographed, and weighed. Tumor tissues are used for western blot analysis and immunohistochemical analysis. References [1]. Kim JE, et al. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3-K. Cancer Prev Res (Phila). 2011 Apr;4(4):582-91. [2]. Hu S, et al. Isorhamnetin inhibits cell proliferation and induces apoptosis in breast cancer via Akt and mitogen activated protein kinase kinase signaling pathways. Mol Med Rep. 2015 Nov;12(5):6745-51. Chemical & Physical Properties Density 1.6±0.1 g/cm3 Boiling Point 599.4±50.0 °C at 760 mmHg Melting Point 307°C Molecular Formula C16H12O7 Molecular Weight 316.262 Flash Point 227.8±23.6 °C Exact Mass 316.058289 PSA 120.36000 LogP 1.76 Vapour Pressure 0.0±1.8 mmHg at 25°C Index of Refraction 1.741 InChIKey IZQSVPBOUDKVDZ-UHFFFAOYSA-N SMILES COc1cc(-c2oc3cc(O)cc(O)c3c(=O)c2O)ccc1O Storage condition 2-8°C |
| Use of | Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K. Properties Articles54 Name isorhamnetin Synonym More Synonyms Isorhamnetin Biological Activity Description Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K. Related Catalog Signaling Pathways >> MAPK/ERK Pathway >> MEK Research Areas >> Cardiovascular Disease Research Areas >> Cancer Natural Products >> Flavonoids Research Areas >> Inflammation/Immunology References [1]. Kim JE, et al. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3-K. Cancer Prev Res (Phila). 2011 Apr;4(4):582-91. [2]. Hu S, et al. Isorhamnetin inhibits cell proliferation and induces apoptosis in breast cancer via Akt and mitogen activated protein kinase kinase signaling pathways. Mol Med Rep. 2015 Nov;12(5):6745-51. Chemical & Physical Properties Molecular Formula C16H12O7 Exact Mass 316.058289 PSA 120.36000 Index of Refraction 1.741 InChIKey IZQSVPBOUDKVDZ-UHFFFAOYSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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