51938-32-0

Basic information

• Product Name: APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE
• Synonyms: 8-(α-L-Arabinopyranosyl)-6-(β-D-glucopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;Shaftoside;6-C-beta-D-Glucosyl-8-C-alpha-L-arabinosylapigenin;Apigenin 8-C-α-L-arabinoside 6-C-β-D-glucoside;4',5,7-Trihydroxy-6-(β-D-glucopyranosyl)-8-(α-L-arabinopyranosyl)flavone;Schaftoside, 98%, from Desmodium styracifolium (Osbeck) Merr.
• CAS NO: 51938-32-0
• Molecular Formula: C₂₆H₂₈O₁₄
• Molecular Weight: 564.5
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;plant extract;Tri-substituted Flavones
• Mol File: 51938-32-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 228℃
• Boiling Point: 935°Cat760mmHg
• Flash Point: 314.3°C
• Appearance: /
• Density: 1.766
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.758
• Storage Temp.: 2-8°C
• PKA: 5.70±0.40(Predicted)
• CAS DataBase Reference: APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE(51938-32-0)
• EPA Substance Registry System: APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE(51938-32-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: DJ2977250
• Hazardous Substances Data: 51938-32-0(Hazardous Substances Data)

Usage

Description

APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE, also known as Schaftoside, is a C-glycosyl compound derived from apigenin, a naturally occurring flavone found in various plants. It is characterized by the presence of beta-D-glucopyranosyl and an alpha-L-arabinopyranosyl moieties at positions 6 and 8, respectively, which are connected to the apigenin molecule through C-glycosidic linkages. This unique structure endows Schaftoside with specific biological activities and potential applications in various fields.

Uses

Used in Pharmaceutical Applications:
APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE is used as an inhibitor of cholesterol gallstone formation, a condition characterized by the presence of solid stones in the gallbladder. APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE exhibits this effect by interfering with the processes that lead to gallstone formation, thereby providing a potential therapeutic option for patients suffering from this condition.
Used in Hepatoprotective Applications:
In the field of hepatoprotection, APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE is used to prevent hepatic fatty degeneration in mice. Hepatic fatty degeneration is a pathological condition where fat accumulates in the liver cells, leading to liver damage and dysfunction. By preventing this process, Schaftoside can help maintain liver health and function, making it a valuable compound for the development of hepatoprotective drugs.
Used in Nutraceutical Industry:
APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE is used as a bioactive compound in the nutraceutical industry for its potential health benefits. Its presence in various plant sources makes it a valuable ingredient for the development of dietary supplements and functional foods that promote overall health and well-being.
Used in Cosmetics Industry:
In the cosmetics industry, APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE is used as an active ingredient in skincare products due to its potential anti-inflammatory, antioxidant, and anti-aging properties. Its incorporation into cosmetic formulations can help improve skin health, reduce signs of aging, and provide protection against environmental stressors.

InChI:InChI=1/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)15-19(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-24(14)16(20(15)34)25-22(36)17(31)11(30)7-38-25/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2/t11-,13+,17-,18+,21-,22+,23+,25-,26-/m0/s1

Upstream product

• 480-41-1 naringenin 
• 1253227-74-5 4'-acetoxy-6-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5,7-dihydroxyflavan 
• 869848-87-3 2,3,4-tri-O-acetyl-α/β-L-arabinopyranosyl trichloroacetimidate 
• 679398-75-5 2-(4-hydroxyphenyl)-5-hydroxy-7-(tert-butyldimethylsiloxy)chroman-4-one 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 

Relevant articles and documents

Efficient total synthesis method and application of natural product schaftoside

The invention belongs to the technical field of chemistry and medicine, and discloses an efficient total synthesis method and application of a natural product schaftoside. The method comprises the steps of subjecting naringenin, tert-butyldimethylsilyl chloride and acetyl chloride to reaction to obtain an intermediate compound 2, and conducting deoxidation reaction to obtain an intermediate compound 3; carrying out rearrangement reaction on the intermediate compound 3 to obtain an intermediate compound 5, and removing a silicon-based protecting group to obtain an intermediate compound 6; carrying out rearrangement reaction on the intermediate compound 6 to obtain an intermediate compound 8; reacting the intermediate compound 8 with benzyl bromide in potassium carbonate to obtain an intermediate compound 9; oxidizing the intermediate compound 9 by ceric ammonium nitrate and pyridinium dichromate to obtain an intermediate compound 10; removing benzyl from the intermediate compound 10 to obtain an intermediate compound 11; and catalyzing the intermediate compound 11 to obtain an intermediate compound 12, and removing acetyl to obtain a target product compound. The method is mild in reaction condition, convenient to operate, economical in raw materials and capable of being used for industrial preparation.

New C,O-Glycosylflavones from the Genus Silene

Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (s