27740-01-8

Basic information

• Product Name: Scutellarin
• Synonyms: 7-(beta-d-glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one;SCUTELLARIN;SCUTELLAREIN 7-O-GLUCURONIDE;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
• CAS NO: 27740-01-8
• Molecular Formula: C₂₁H₁₈O₁₂
• Molecular Weight: 462.36
• EINECS: 1806241-263-5
• Product Categories: Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 27740-01-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 300～301℃
• Boiling Point: 891.6 °C at 760 mmHg
• Flash Point: 314.9 °C
• Appearance: /
• Density: 1.81 g/cm³
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Very Slightly, Sonicated)
• PKA: 2.72±0.70(Predicted)
• BRN: 71779
• CAS DataBase Reference: Scutellarin(CAS DataBase Reference)
• NIST Chemistry Reference: Scutellarin(27740-01-8)
• EPA Substance Registry System: Scutellarin(27740-01-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 27740-01-8(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 27740-01-8 differently. You can refer to the following data:
1. 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.
2. 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.

InChI:InChI=1/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1

Synthetic route

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

Conditions	Yield
Stage #1: scutellarein 7-O-β-D-glucuronopyranoside methyl ester With water; sodium hydroxide In acetone at 0℃; for 0.2h; Inert atmosphere; Stage #2: With hydrogenchloride In water; acetone for 1h; pH=2-3; Reagent/catalyst; Temperature; Time; Concentration;	89%

scutellarein (529-53-3) + UDP-glucuronic acid (2616-64-0) → scutellarin (27740-01-8)

Conditions	Yield
With Tris-HCl buffer; UDP-glucuronate: baicalein 7-O-glucuronosyltransferase In water at 37℃; pH=7.5; Enzyme kinetics; Esterification; Enzymatic reaction;
With Veronica persica UDP-dependent glycosyl transferase 88D8 In potassium phosphate buffer at 30℃; pH=7.5;

Upstream product

• 529-53-3 scutellarein 
• 119262-68-9 scutellarein 7-O-β-D-glucuronopyranoside methyl ester 
• 54917-66-7 5,6,4'-triacetoxy-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester) 
• 1180-46-7 4,5,6,7-tetra-O-acetylflavone 
• 1432474-30-0 C₂₇H₂₅NO₁₇ 
• 1432474-29-7 C₂₈H₂₇NO₁₇ 
• 1432474-28-6 C₃₂H₂₉NO₁₅ 
• 1432474-27-5 C₂₈H₂₉NO₁₅ 
• 1432474-26-4 C₂₆H₂₅NO₁₅ 
• 2616-64-0 UDP-glucuronic acid 

Downstream Products

• 1424769-70-9 mono[6-(scutellarin)amino-6-deoxy]-β-cyclodextrin 
• 1424769-72-1 mono[6-(scutellarin)ethyleneamino-6-deoxy]-β-cyclodextrin 
• 1424769-75-4 C₆₇H₉₇N₃O₄₅ 
• 54917-66-7 5,6,4'-triacetoxy-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester) 

Relevant articles and documents

Total synthesis of scutellarin and apigenin 7-O-β-d-glucuronide

A general protocol for direct glucuronic linkages formation featuring Au(I)-catalyzed appropriately protected glucuronyl o-alkynylbenzoate-involved glycosylation reaction, as well as a concise approach for easy access of scutellarein prominent for the mild and efficient hydroxyl group installation via borylation-oxidation sequence from flavanone derivative, has been established, based on which a novel route for scutellarin derivatives preparation has been devised. The developed strategies, among which the stepwise deprotection process was also included, guarantee the high whole synthetic efficiency, and definitely will find broad application in diversity-oriented synthesis of bioactive flavonoid glycosides.

Synthesis and physiochemical property evaluation of carbamate derivatives of scutellarin methyl ester

A series of carbamate prodrugs of scutellarin methyl ester (4a-4e) were prepared in the presence of bis(trichloromethyl) carbonate (BTC) with scutellarin methyl esters and l-amino acid tert-butyl ester hydrochloride as starting materials. In vitro stability and aqueous solubility of target compounds were evaluated. The results indicated that compounds 4d and 4e have higher solubility and in vitro stability than scutellarin respectively.

Purification and characterization of UDP-glucuronate: Baicalein 7-O- glucuronosyltransferase from Scutellaria baicalensis Georgi. cell suspension cultures

UDP-glucuronate: baicalein 7-O-glucuronosyltransferase (UBGAT) catalyzes the transfer of glucuronic acid from UDP-glucuronic acid to the 7-OH of baicalein. UBGAT was purified from cultured cells of Scutellaria baicalensis Georgi (Lamiaceae). It was purified 95-fold using various chromatography and chromatofocusing procedures to apparent homogeneity. The M(r) was estimated to be 110 kDa by gel filtration chromatography with a 52 kDa subunit by SDS- PAGE. The isoelectric point was pH 4.8. UBGAT was specific to UDP-glucuronic acid as a sugar donor and flavones with substitution ortho- to the 7-OH group such as baicalein (6-OH), scutellarein (6-OH) and wogonin (8-OMe). (C) 2000 Elsevier Science Ltd.