29838-67-3

Basic information

• Product Name: TAXIFOLIN 3-O-RHAMNOSIDE
• Synonyms: (2S,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-chroman-4-one;(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-chroman-4-one;Taxifolin 3-o-rhamnoside;Astilbin;Astilbin Taxifolin 3-O-rhaMnoside;(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chroMen-3-yl 6-deoxy-alpha-L-Mannopyranoside;Taxifolin 3-rhaMnoside;Astilbin froM Engelhardtia roxburghiana
• CAS NO: 29838-67-3
• Molecular Formula: C₂₁H₂₂O₁₁
• Molecular Weight: 450.4
• EINECS: 300-009-0
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Astilbin ada@tuskwei.com
• Mol File: 29838-67-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 180 °C (decomp)
• Boiling Point: 801.1 °C at 760 mmHg
• Flash Point: 282.9 °C
• Appearance: /
• Density: 1.74
• Vapor Pressure: 4.42E-27mmHg at 25°C
• Refractive Index: 1.748
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble1mg/mL, clear, colorless
• PKA: 7.34±0.60(Predicted)
• CAS DataBase Reference: TAXIFOLIN 3-O-RHAMNOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TAXIFOLIN 3-O-RHAMNOSIDE(29838-67-3)
• EPA Substance Registry System: TAXIFOLIN 3-O-RHAMNOSIDE(29838-67-3)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 29838-67-3(Hazardous Substances Data)

Usage

Description

TAXIFOLIN 3-O-RHAMNOSIDE, also known as a flavanone glycoside, is a compound in which (+)-taxifolin is substituted by an alpha-L-rhamnosyl moiety at position 3 through a glycosidic linkage. It is a naturally occurring compound with potential biological activities and applications in various fields.

Uses

Used in Pharmaceutical Industry:
TAXIFOLIN 3-O-RHAMNOSIDE is used as a pharmaceutical compound for its potential therapeutic effects. It has been found to possess diverse biological activities, including anti-depressant, anti-oxidant, and anti-cancer properties. TAXIFOLIN 3-O-RHAMNOSIDE may modulate various signaling pathways and exhibit synergistic effects when combined with conventional drugs, enhancing their efficacy and sensitivity in resistant cases.
Used in Nutraceutical Industry:
TAXIFOLIN 3-O-RHAMNOSIDE is used as a nutraceutical ingredient for its health-promoting and disease-preventing properties. It has been shown to increase renal glutathione levels, superoxide dismutase and catalase activity, and reduce serum creatinine and blood urea nitrogen levels, renal inflammation, and apoptosis in kidney tissue. Additionally, it may reduce the loss of dopaminergic neurons in the substantia nigra and improve motor deficits in Parkinson's disease models.
Used in Cosmetic Industry:
TAXIFOLIN 3-O-RHAMNOSIDE is used as an active ingredient in the cosmetic industry for its potential anti-aging, anti-inflammatory, and skin protective effects. TAXIFOLIN 3-O-RHAMNOSIDE's antioxidant and anti-inflammatory properties may contribute to improved skin health and reduced signs of aging.
Used in Drug Delivery Systems:
TAXIFOLIN 3-O-RHAMNOSIDE is used as a component in drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes. Various organic and metallic nanoparticles can be employed as carriers for TAXIFOLIN 3-O-RHAMNOSIDE, aiming to improve its effectiveness in targeted applications.

InChI:InChI=1/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1

Upstream product

• 29838-67-3 astilbin 
• 294203-79-5 (2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one 
• 80152-99-4 1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose 
• 104495-20-7 2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 294203-76-2 (2R,3S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman 
• 294203-78-4 (2R,3S,4S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-ol 

Downstream Products

• 122147-54-0 (2R)-2r-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3t-α-L-rhamnopyranosyloxy-chroman-4-one 
• 121707-94-6 (2R)-5,7-diacetoxy-2r-(3,4-diacetoxy-phenyl)-3t-(tri-O-acetyl-α-L-rhamnopyranosyloxy)-chroman-4-one 
• 29838-67-3 (2S,3R)-dihydroquercetin 3-O-α-L-rhamnoside 
• 480-18-2 (+/-)-taxifolin 
• 480-18-2 taxifolin 
• 73-34-7 L-rhamnose 
• 215257-15-1 3,3',4',5,7-pentahydroxy flavanone 
• 54081-47-9 Neoastilbin 
• 29838-67-3 (2R,3S)-dihydroquercetin 3-O-α-L-rhamnoside 
• 6563-36-6 (+)-3',4',5,7-tetra-O-methyl-2,3-trans-dihydroquercetin 

Relevant articles and documents

Cationic zirconocene- or hafnocene-based Lewis acids in organic synthesis: Glycoside-flavonoid analogy

Cationic metallocene species, generated from Cp2MCl2 and AgClO4 (M=Zr, Hf), were used for the glycosylation of catechin derivative 2, enabling a concise synthesis of a glycosyl flavonoid, astilbin (1). Further study revealed the efficiency of this Lewis acidic species for SN1-type activation of the C(4) position of catechin derivative 11, enabling selective substitution with various nucleophiles.

First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine

A synthetic route to a biologically active glycosyl flavonoid, astilbin (1), was developed. The tetra-benzyl ether 4, derived from (+)-catechin, was glycosylated with the L-rhamnosyl donor 10 by using Cp2HfCl2-AgClO4, and subsequent oxidation of the C(4)position of the flavan skeleton followed by deprotection gave 1. (C) 2000 Elsevier Science Ltd.