578-74-5

Basic information

• Product Name: Apigenin 7-glucoside
• Synonyms: COSMETIN;COSMIIN;COSMOSIIN;APIGENIN-7-O-GLUCOSIDE;APIGENIN-7-GLUCOSIDE;APIGETRIN;7-O-BETA-D-GLUCOPYRANOSYLOXY-4',5-DIHYDROXYFLAVONE;7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• CAS NO: 578-74-5
• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.38
• EINECS: 209-430-5
• Product Categories: Tri-substituted Flavones;Flavones;Pharmaceutical intermediate;chemical reagent;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 578-74-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 230-237°C
• Boiling Point: 788.9 °C at 760 mmHg
• Flash Point: 280.7 °C
• Appearance: /
• Density: 1.642 g/cm³
• Vapor Pressure: 3.14E-26mmHg at 25°C
• Refractive Index: 1.717
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly, Sonicated), Methanol (Slightly)
• PKA: 6.13±0.40(Predicted)
• BRN: 65669
• CAS DataBase Reference: Apigenin 7-glucoside(CAS DataBase Reference)
• NIST Chemistry Reference: Apigenin 7-glucoside(578-74-5)
• EPA Substance Registry System: Apigenin 7-glucoside(578-74-5)

Safety Data

• Safety Statements: 34/35
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 578-74-5(Hazardous Substances Data)

Usage

Uses

Apigenin 7-Glucoside is a by-product during the synthesis of Isorhoifolin (I819700), a naturally occurring flavonoid that was shown to exhibit potential antidiabetic, antihyperlipidemic and antioxidant effects.

Definition

ChEBI: A glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.

InChI:InChI=1/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18+,19+,20-,21-/m1/s1

Upstream product

• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 123656-62-2 crotonoylcosmosiin 
• 83529-71-9 anisofolin-A 
• 26544-34-3 apiin 
• 119249-30-8 7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin 
• 31087-58-8 7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 23598-19-8 4'-O-benzylapigenin-7-O-β-D-tetra-O-acetylglucoside 
• 52309-82-7 4′-O-benzylapigenin 
• 10236-47-2 naringin 
• 17306-46-6 rhoifolin 
• 133-89-1 UDP-glucose 
• 2196-14-7 7,4'-Dihydroxyflavon 

Downstream Products

• 70522-70-2 5-methoxy-2-(4-methoxy-phenyl)-7-(tetra-O-methyl-β-D-glucopyranosyloxy)-chromen-4-one 
• 2280-44-6 D-Glucose 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 50-99-7 D-glucose 
• 26544-34-3 apiin 

Relevant articles and documents

AN ACYLATED FLAVONE APIGENIN 7-O-β-D-(4''-CIS-p-COUMAROYL)GLUCOSIDE FROM ECHINOPS ECHINATUS

Besides apigenin 7-O-glucoside, a new acylated flavone has been identified in Echinops echinatus as apigenin 7-O-β-D-(4''-cis-p-coumaroyl)glucoside from spectral and chemical analysis. Key Word Index - Echinops echinatus; Compositae; glycosylflavones; apigenin 7-O-glucoside; apigenin 7-O-β-D-(4''-cis-p-coumaroyl)glucopyranoside; FD-MS; 13C NMR.

Identification of a flavonoid 7-O-glucosyltransferase from Andrographis paniculata

Andrographis paniculata is an important traditional medicinal herb in which flavonoids are part of the primary specialized metabolites. A flavonoid glucosyltransferase with broad substrate spectrum (named ApUGT3) was successfully identified by screening homologous glycosyltransferase genes from A. paniculata. The enzyme displayed glycosylation activity toward multiple flavonoids in?vitro, and the major products were identified as 7-O-glucosides. Phylogenetic analysis revealed that ApUGT3 is the first reported glycosyltransferase from the Acanthaceae family that belongs to cluster I, suggesting that ApUGT3 is a new flavonoid glycosyltransferase of this subcluster. This enzyme is potentially useful as powerful glycosylation catalysts to modify flavonoid-like compounds and improve their biological activities. (Figure presented.).

Highly regioselective dehexanoylation in fully hexanoylated flavonoids

Highly selective removal of the 7-O-hexanoyl group in fully hexanoylated flavones, isoflavones, flavanone, and flavonol was achieved under mild conditions using K2CO3 in a 1:1 mixture of CH3OH–CH2Cl2. The resulting 7-OH flavonoids are valuable intermediates for the synthesis of flavonoid 7-O-glycosides via phase-transfer-catalyzed (PTC) glycosylation.

Preparation method of flavone aglycone or monoglycoside from aluminum-salt-flavonoid-glycoside complex through hydrolysis

Disclosed is a preparation method of flavone aglycone or monoglycoside from aluminum-salt-flavonoid-glycoside complex through hydrolysis. The problems that flavonoid glycosides neither dissolve in water nor are hard to dissolve in a common organic alcohol solution, and flavone aglycone prepared from hydrolysis has slow hydrolysis speed, needs a large amount of an organic solvent, and cannot be totally hydrolyzed are solved. A complex product from complexation of aluminum salt and flavonoid glycosides is easy to dissolve in alcohol, hydrogen chloride generated by the complex product is utilized with addition of hydrochloric acid or sulfuric acid, and hydrolysis is carried out at a certain temperature to prepare aglycone or a mixture of aglycone and monoglycoside. After the reaction is over, phosphoric acid or phosphate is added to break complexation of aluminum ions and flavone to obtain flavone aglycone, or the mixture of flavone aglycone and flavone monoglycoside, or a mixture of flavone aglycone, flavone monoglycoside, and flavonoid glycoside. The method is simple and easy to operate, relatively high in yield and purity, and extremely low in cost, and is suitable for massive industrial production of flavone aglycone or the mixture of flavone aglycone and flavone monoglycoside.