| Identification | More | [Name]
Scutellarin | [CAS]
27740-01-8 | [Synonyms]
7-(beta-d-glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one
SCUTELLAREIN 7-O-GLUCURONIDE
SCUTELLARIN
SCUTELLARIN, 98+% BY HPLC
(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl
β-D-Glucopyranosiduronicacid,5,6-dihydroxy-2-
4',5,6-Trihydroxy-7-[(β-D-glucopyranuronosyl)oxy]flavone
4',5,6-Trihydroxyflavon-7-yl β-D-glucopyranosiduronic acid
5,6-Dihydroxy-4-oxo-2-(4-hydroxyphenyl)-4H-1-benzopyran-7-yl β-D-glucopyranosiduronic acid
Scutellarein 4'-methyl ether 7-glucuronide
Scutellarein 7-glucuronide | [EINECS(EC#)]
1806241-263-5 | [Molecular Formula]
C21H18O12 | [MDL Number]
MFCD01861503 | [Molecular Weight]
462.36 | [MOL File]
27740-01-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
300～301℃ | [Boiling point ]
891.6±65.0 °C(Predicted) | [density ]
1.810±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Very Slightly, Sonicated) | [form ]
neat | [pka]
2.72±0.70(Predicted) | [color ]
Light Yellow to Yellow | [BRN ]
71779 | [Major Application]
food and beverages | [InChIKey]
DJSISFGPUUYILV-ZWDBVKRXNA-N | [SMILES]
O=C1C=C(C2C=CC(O)=CC=2)OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](C(=O)O)O3)O)=C(O)C(O)=C12 |&1:16,17,18,20,22,r| | [CAS DataBase Reference]
27740-01-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Scutellarin is a flavone that has been found in S. barbata and has diverse biological activities, including anticancer, lipid lowering, antioxidative, and neurocognitive properties.1,2,3 It inhibits proliferation of PC-9 and H1975 non-small cell lung cancer (NSCLC) cells in a concentration-dependent manner and induces apoptosis and autophagy when used at a concentration of 160 μM, effects that can be blocked by the autophagy inhibitor HCQ (Item No. 17911).1 Scutellarin (30 and 60 mg/kg per day) reduces tumor growth in an H1975 mouse xenograft model. It decreases serum total cholesterol and LDL-cholesterol and increases HDL-cholesterol in a high-fat diet-induced mouse model of non-alcoholic fatty liver disease (NAFLD) when administered at doses of 25 and 50 mg/kg.2 It decreases hepatic malondialdehyde (MDA), glutamic-oxalacetic transaminase (GOT), and glutamic-pyruvic transaminase (GPT) activity, increases catalase (CAT) and total antioxidative capacity (T-AOC) activity, and increases the hepatic expression of PPARγ, PGC-1α, and Nrf2 in the same model. Scutellarin (5, 25, and 50 mg/kg per day) also prevents deficits in spatial and novel object memory in rats in the Y maze and novel object recognition test, respectively.3 | [Chemical Properties]
Soluble in alkali, acetic acid, pyridine, slightly soluble in general organic solvents, insoluble in water. It is recommended to use DMSO to dissolve the leaves of Scutellaria altissima L., a plant of the Labiatae family. | [Uses]
Scutellarin is an active flavonoid component from the medical plant Erigeron breviscapus (Vant) Hand-Mazz. Scutellarin is used as a micrpcirculation promoter for the treatment of cardio-cerebrovascula
r diseases. Studies suggest that Scutellarin has anti-cancer properties and has been shown to enhance apoptosis of tumor cells. | [Definition]
ChEBI: The glycosyloxyflavone which is the 7-O-glucuronide of scutellarein. | [Synthesis]
General procedure: 20 g (42 mmol) of methyl (2S,3S,4S,5R,6S)-6-((5,6-dihydroxy-2-(4-hydroxyphenyl)-4-yloxy-4H-benzopyran-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate was dissolved in a mixed solvent of 300 mL of water and 300 mL of acetone at 0 °C Stirring. Under the protection of nitrogen, 70 mL of 10% aqueous sodium hydroxide solution was slowly added dropwise, and the reaction temperature was maintained at 0 °C with continuous stirring for about 2 h. The reaction process was monitored by HPLC. After the reaction was completed, 10% hydrochloric acid aqueous solution was slowly added dropwise under stirring to adjust the pH of the reaction solution to 2.0-3.0, and stirring was continued for 1 hour. Subsequently, the reaction system was gradually brought to room temperature and a large amount of yellow solid 5,6,4'-trihydroxyflavone-7-yloxy-glucuronic acid was observed to precipitate gradually. The reaction mixture was allowed to stand at room temperature overnight, followed by diafiltration and the filter cake was washed with appropriate amount of water and acetone and dried. Finally, purification by ethanol recrystallization afforded 17.3 g of pure 5,6,4'-trihydroxyflavone-7-yloxy-glucuronic acid in 89% yield. The purity of the product was 98.74% by HPLC, and its HPLC chromatogram is shown in Fig. 1, and the statistical results are shown in Table 1.1H-NMR (400 MHz, DMSO) data were as follows: δ 10.41 (1H, s), 8.63 (1H, s), 7.94 (2H, d, J = 8.8Hz), 6.99 (1H, s), 6.94 (2H, d, J = 8.8Hz), 6.99 (1H, s), 6.94 (2H, d, J = 8.8Hz). d, J = 8.8 Hz), 6.86 (1H, s), 5.51-5.31 (3H, br), 5.28 (1H, d, J = 7.5 Hz), 4.11 (2H, d, J = 9.6 Hz), 3.43 (4H, m). | [in vivo]
Scutellarin (50 mg/kg/day) significantly mitigates the lung and intrahepatic metastasis of HCC tumors in vivo. The numbers of the lung and intrahepatic metastatic tumors in the scutellarin-treated group are significantly less than that in the controls[1]. The rats treated with Scutellarin display a significant alleviation in neurobehavioral deficits compared to the SAH group. Scutellarin enhanced eNOS expression compared with SAH rats[4]. | [IC 50]
STAT3; HIV-1 | [References]
[1] Patent: EP2840088, 2015, A1. Location in patent: Paragraph 0042 |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Adamas Reagent, Ltd.
|
| Telephone: |
4006009262 13023226327 |
| Website: |
http://www.tansoole.com |
| Company Name: |
China Langchem Inc.
|
| Telephone: |
0086-21-58956006 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList19141/0_EN.htm |
|