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

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

Used in Pharmaceutical Industry:
Iriflophene 3-C-beta-D-glucopyranoside is used as a therapeutic agent for preventing and treating oxygen free radical-associated diseases. Its antioxidant properties help in neutralizing harmful free radicals, thereby reducing the risk of oxidative stress-related disorders.
Used in Nutraceutical Industry:
Iriflophene 3-C-beta-D-glucopyranoside can be used as a functional ingredient in nutraceutical products, such as dietary supplements and health drinks, to provide antioxidant support and promote overall health.
Used in Cosmetic Industry:
Due to its antioxidant properties, Iriflophene 3-C-beta-D-glucopyranoside can be utilized in cosmetic products to protect the skin from oxidative damage, reduce the signs of aging, and maintain skin health.
Used in Agricultural Industry:
Iriflophene 3-C-beta-D-glucopyranoside can be employed as a natural antioxidant in the agricultural sector to enhance the shelf life of fruits and vegetables, as well as to improve the overall quality of agricultural products.

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

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

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.

Enzymatic Synthesis of Acylphloroglucinol 3-C-Glucosides from 2-O-Glucosides using a C-Glycosyltransferase from Mangifera indica

A green and cost-effective process for the convenient synthesis of acylphloroglucinol 3-C-glucosides from 2-O-glucosides was exploited using a novel C-glycosyltransferase (MiCGTb) from Mangifera indica. Compared with previously characterized CGTs, MiCGTb exhibited unique de-O-glucosylation promiscuity and high regioselectivity toward structurally diverse 2-O-glucosides of acylphloroglucinol and achieved high yields of C-glucosides even with a catalytic amount of uridine 5′-diphosphate (UDP). These findings demonstrate for the first time the significant potential of a single-enzyme approach to the synthesis of bioactive C-glucosides from both natural and unnatural acylphloroglucinol 2-O-glucosides. One enzyme, one product: A novel C-glycosyltransferase from Mangifera indica is reported, which is a promiscuous catalyst that synthesizes bioactive C-glucosides from natural and unnatural acylphloroglucinol 2-O-gulcosides in one-pot reactions. High yields of C-glucosides were achieved even with a catalytic amount of uridine 5′-diphosphate. This study demonstrates for the first time the significant potential of a single-enzyme approach for the C-glycodiversification.

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