Scutellarin

Base Information

• Chemical Name: Scutellarin
• CAS No.: 27740-01-8
• Deprecated CAS: 1329-06-2,32647-60-2,676536-34-8
• Molecular Formula: C21H18O12
• Molecular Weight: 462.367
• Hs Code.: 29389090
• UNII: 16IGP0ML9A
• DSSTox Substance ID: DTXSID101336184
• Nikkaji Number: J94.485H
• Wikipedia: Scutellarin
• Wikidata: Q410712
• Metabolomics Workbench ID: 61563
• ChEMBL ID: CHEMBL487805
• Mol file: 27740-01-8.mol

Synonyms:beta-D-glucopyranosiduronic acid, 5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl;flavone, 4',5,6,7-tetrahydroxy-, 7-beta-D-glucopyranuronoside;scutellarein 7-beta-D-glucuronide;scutellarein 7-beta-D-glucuronoside;scutellarein 7-glucuronide;scutellarein 7-O-beta-D-glucuronide;scutellarein-7-O-beta-glucuronide;scutellarein-7-O-glucuronide;scutellarin;scutellarin B

Chemical Property of Scutellarin

Chemical Property:

• Melting Point: 300～301℃
• Boiling Point: 891.6 °C at 760 mmHg
• PKA: 2.72±0.70(Predicted)
• Flash Point: 314.9 °C
• PSA: 207.35000
• Density: 1.81 g/cm³
• LogP: -0.15220
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Sonicated)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 4
• Exact Mass: 462.07982601
• Heavy Atom Count: 33
• Complexity: 777

Purity/Quality:

99% ^*data from raw suppliers

Scutellarin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O)O)O
• 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. 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 . 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. 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.
• 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-cerebrovascular diseases. Studies suggest that Scutellarin has anti-cancer properties and has been shown to enhance apoptosis of tumor cells. 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.

Technology Process of Scutellarin

There total 17 articles about Scutellarin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

scutellarein 7-O-β-D-glucuronopyranoside methyl ester (119262-68-9) → scutellarin (27740-01-8,676536-34-8)

Guidance literature:

scutellarein 7-O-β-D-glucuronopyranoside methyl ester; With water; sodium hydroxide; In acetone; at 0 ℃; for 0.2h; Inert atmosphere;

With hydrogenchloride; In water; acetone; for 1h; pH=2-3; Reagent/catalyst; Temperature; Time; Concentration;

Reference yield:

C56H48O12 → scutellarin (27740-01-8,676536-34-8)

Guidance literature:

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; methanol; at 20 ℃;

DOI:10.1016/j.carres.2019.02.005

Reference yield:

scutellarein (529-53-3) → scutellarin (27740-01-8,676536-34-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 0.9 h / 180 °C

2.1: potassium carbonate; potassium iodide / acetone / 0.18 h / 20 °C

3.1: nitric acid / methanol / 0.8 h / Reflux

4.1: water; sodium hydroxide / acetone / 0.2 h / 0 °C / Inert atmosphere

4.2: 1 h / pH 2-3

With pyridine; water; nitric acid; potassium carbonate; potassium iodide; sodium hydroxide; In methanol; acetone;

upstream raw materials:

scutellarein

UDP-glucuronic acid

C₂₆H₂₅NO₁₅

C₂₈H₂₉NO₁₅

Downstream raw materials:

scutellarein 7-O-β-D-glucuronopyranoside methyl ester

4,5,6,7-tetra-O-acetylflavone

5,6,4'-triacetoxy-3-chloro-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester)

5,6,7,4'-tetraacetoxy-8-chloroflavone

Refernces

• 1、 -. "METHOD FOR PREPARING 5,6,4'-TRIHYDROXYFLAVONE-7-0-D-GLUCURONIC ACID". . . Retrieved 2015/03/13.
• 2、 Ono, Eiichiro,Ruike, Miho,Iwashita, Takashi,Nomoto, Kyosuke,Fukui, Yuko. "Co-pigmentation and flavonoid glycosyltransferases in blue Veronica persica flowers". experimental part. p. 726 - 735. Retrieved 2010/07/02.