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, also known as the 7-O-glucuronide of scutellarein, is a flavone with diverse biological activities. It is an active flavonoid component found in the medical plant Erigeron breviscapus (Vant) Hand-Mazz. Scutellarin possesses anticancer, lipid-lowering, antioxidative, and neurocognitive properties. It inhibits the proliferation of non-small cell lung cancer (NSCLC) cells and induces apoptosis and autophagy. Scutellarin also has beneficial effects on cholesterol levels and liver health, as well as improving cognitive function in rats.

Uses

Used in Cardio-cerebrovascular Applications:
Scutellarin is used as a microcirculation promoter for the treatment of cardio-cerebrovascular diseases. It helps improve blood flow and circulation in the heart and brain, which can be beneficial for patients with these conditions.
Used in Anticancer Applications:
Scutellarin is used as an anticancer agent, particularly for non-small cell lung cancer (NSCLC). It has been shown to inhibit the proliferation of cancer cells in a concentration-dependent manner and enhance apoptosis of tumor cells. Scutellarin has the potential to be a promising pharmaceutical candidate for cancer treatment.
Used in Lipid-Lowering Applications:
Scutellarin is used as a lipid-lowering agent in a high-fat diet-induced mouse model of non-alcoholic fatty liver disease (NAFLD). It decreases serum total cholesterol and LDL-cholesterol while increasing HDL-cholesterol, which can help improve overall lipid profile and reduce the risk of cardiovascular diseases.
Used in Antioxidative Applications:
Scutellarin is used as an antioxidant, reducing hepatic malondialdehyde (MDA) levels and increasing the activity of catalase (CAT) and total antioxidative capacity (T-AOC). This helps protect the liver from oxidative stress and damage.
Used in Neurocognitive Applications:
Scutellarin is used to prevent deficits in spatial and novel object memory in rats, as demonstrated in the Y maze and novel object recognition test. This suggests that Scutellarin may have potential applications in improving cognitive function and treating neurocognitive disorders.

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

Downstream Products

• 119262-68-9 scutellarein 7-O-β-D-glucuronopyranoside methyl ester 
• 1180-46-7 4,5,6,7-tetra-O-acetylflavone 
• 1374218-48-0 5,6,4'-triacetoxy-3-chloro-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester) 
• 1373921-90-4 5,6,7,4'-tetraacetoxy-8-chloroflavone 
• 1374218-50-4 5,6,4'-triacetoxy-8-bromo-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester) 
• 1373922-27-0 5,6,7,4'-tetraacetoxy-3-bromoflavone 
• 1373922-21-4 5,6,7,4'-tetraacetoxy-8-bromoflavone 
• 1374218-52-6 5,6,7,4'-tetraacetoxy-8-iodoflavone 
• 1374218-61-7 6,4'-diacetoxy-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester) 
• 1374218-54-8 6,4'-diacetoxy-7-hydroxyflavon-8-nitro-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester) 
• 1374218-56-0 5,6,7,4'-tetraacetoxy-8-nitroflavone 
• 1374218-62-8 6,4'-diacetoxy-7-hydroxyflavon-8-amino-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester) 
• 1374218-58-2 C₁₉H₁₅NO₈ 
• 1374218-60-6 6,4'-diacetoxy-5-hydroxy-3-oxa-1,2-diaza-cyclopenta[α]flavone 

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.