104669-02-5

Basic information

• Product Name: Iriflophene 3-C-beta-D-glucopyraside
• Synonyms: Iriflophene 3-C-beta-D-glucopyraside;Iriflophenone 3-C-beta-D-glucopyranoside;Iriflophenone 3-C-glucoside;Iriflophenone 3-C-β-D-glucopyranoside;(3-β-D-Glucopyranosyl-2,4,6-trihydroxyphenyl)(4-hydroxyphenyl)methanone;Iriflophenone 3-C-β-D-glucoside;Iriophenone 3-C-glucoside
• CAS NO: 104669-02-5
• Molecular Formula: C₁₉H₂₀O₁₀
• Molecular Weight: 408.3561
• Mol File: 104669-02-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 669.9°Cat760mmHg
• Flash Point: 239.9°C
• Appearance: /
• Density: 1.68g/cm³
• Vapor Pressure: 7.34E-19mmHg at 25°C
• Refractive Index: 1.734
• PKA: 7.04±0.50(Predicted)
• BRN: 5659115
• CAS DataBase Reference: Iriflophene 3-C-beta-D-glucopyraside(CAS DataBase Reference)
• NIST Chemistry Reference: Iriflophene 3-C-beta-D-glucopyraside(104669-02-5)
• EPA Substance Registry System: Iriflophene 3-C-beta-D-glucopyraside(104669-02-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 104669-02-5(Hazardous Substances Data)

Usage

Uses

Iriflophenone 3-C-b-D-Glucopyranoside is a compound of Mangifera indica leaves extract for preventing and treating oxygen free radical-associated diseases.

InChI:InChI=1/C19H20O10/c20-6-11-15(25)17(27)18(28)19(29-11)13-10(23)5-9(22)12(16(13)26)14(24)7-1-3-8(21)4-2-7/h1-5,11,15,17-23,25-28H,6H2/t11-,15-,17+,18-,19+/m1/s1

Upstream product

• 92631-87-3 iriflophenone 3-C-(2′,6′-di-O-galloyl)-glucoside 
• 92631-88-4 iriflophenone 3-C-(2′,3′,6′-tri-O-galloyl)-glucoside 
• 133-89-1 UDP-glucose 
• 52591-10-3 4,2',4',6'-tetrahydroxybenzophenone 

Relevant articles and documents

Benzophenone C - And O -glucosides from Cyclopia genistoides (Honeybush) inhibit mammalian α-glucosidase

An enriched fraction of an aqueous extract prepared from the aerial parts of Cyclopia genistoides Vent. yielded a new benzophenone di-C,O-glucoside, 3-C-β-d-glucopyranosyl-4-O-β-d-glucopyranosyliriflophenone (1), together with small quantities of a known benzophenone C-glucoside, 3-C-β-d-glucopyranosylmaclurin (2). The isolated compounds showed α-glucosidase inhibitory activity against an enzyme mixture extracted from rat intestinal acetone powder. Compound 2 exhibited significantly (p 0.05) higher inhibitory activity (54%) than 1 (43%) at 200 μM. In vitro tests in several cell models showed that 1 and its 3-C-monoglucosylated derivative (3-C-β-d-glucopyranosyliriflophenone) were marginally effective (p ≥ 0.05) in increasing glucose uptake.

Tannins and Related Compounds. XXI. Isolation and Characterization of Galloyl and p-Hydroxybenzoyl Esters of Benzophenone and Xanthone C-glucosides from Mangifera indica L.

Six new galloyl and p-hydroxybenzoyl esters (2-7) of benzophenone C-glucosides have been isolated, together with a new benzophenone C-glucoside (1), from the leaves of Mangifera indica L. (Anacardiaceae).On the basis of chemical and spectroscopic evidence, the structures of these compounds have been established as maclurin 3-C-β-D-glucoside (1), maclurin 3-C-(6''-O-p-hydroxybenzoyl)-β-D-glucoside (2), maclurin 3-C-(2''-O-galloyl-6''-O-p-hydroxybenzoyl)-β-D-glucoside (3), maclurin 3-C-(2''-O-p-hydroxybenzoyl-6''-O-galloyl)-β-D-glucoside (4), maclurin 3-C-(2'',3'',6''-tri-O-galloyl)-β-D-glucoside (5), iriflophenone 3-C(2'',6''-di-O-galloyl)-β-D-glucoside (6) and iriflophenone 3-C-(2'',3'',6''-tri-O-galloyl)-β-D-glucoside (7). (-)-Epicatechin 3-O-gallate (9), mangiferin (10), isomangiferin (11) and a new xanthone C-glucoside gallate, mangiferin 6'-O-gallate (8), have also been isolated and their structures have been similarly characterized.Furthermore, the above plant source contained polygalloylglucoses which were characterized on the basis of chemical and high performance liquid chromatographic analyses as a mixture of penta- to undecagalloylglucoses based on a 1,2,3,4,6-penta-O-galloyl-β-D-glucose core.Maclurin 3-C-glucoside (1) has been transformed enzymatically to mangiferin (10) and isomangiferin (11), and it has become clear that 1 is a key intermediate in the biosynthesis of 10 and 11. Keywords - Mangifera indica; Anacardiaceae; galloyl maclurin 3-C-glucoside p-hydroxybenzoate; galloyl iriflopenone 3-C-glucoside; galloyl mangiferin; benzophenone C-glucoside; biosynthesys; mangiferin; isomangiferin; galloylglucose