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

Astilbin is a flavonoid that has been found in S. glabra and has diverse biological activities. It inhibits cisplatin-induced increases in apoptosis and accumulation of reactive oxygen species (ROS) in HEK293 cells when used at a concentration of 200 μM. Astilbin (50 mg/kg) increases renal glutathione (GSH) levels and superoxide dismutase (SOD) and catalase activity and reduces serum creatinine and blood urea nitrogen (BUN) levels, renal IL-1β, IL-6, and TNF-α levels, apoptosis in kidney tissue, and kidney injury in a mouse model of cisplatin-induced nephrotoxicity. It reduces loss of dopaminergic neurons in the substantia nigra and increases striatal GSH levels and SOD activity in a mouse model of MPTP-induced Parkinson''s disease when administered at a dose of 50 mg/kg per day. Astilbin also reduces descent time in a pole test and increases traction test score in a mouse model of Parkinson''s disease, indicating reduced motor deficits. It reduces cell viability of MDA-MB-231 and MCF-7 cells (IC50s = 167.9 and 191.6 μM, respectively), as well as inhibits migration and increases apoptosis when used at concentrations of 50 and 200 μM. Astilbin (20 mg/kg every other day for 14 days) reduces tumor growth in an MCF-7 mouse xenograft model.

Uses

Astilbin displays anti-depressant activity involving monoaminergic neurotransmitters an the BDNF signal pathway. Anti-oxidant.

Definition

ChEBI: A flavanone glycoside that is (+)-taxifolin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage.

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 
• 294203-78-4 (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 
• 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 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 104495-20-7 2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride 
• 80152-99-4 1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose 
• 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 

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 
• 29838-67-3 (2R,3S)-dihydroquercetin 3-O-α-L-rhamnoside 
• 73-34-7 L-rhamnose 
• 215257-15-1 3,3',4',5,7-pentahydroxy flavanone 
• 480-18-2 taxifolin 
• 6563-36-6 (+)-3',4',5,7-tetra-O-methyl-2,3-trans-dihydroquercetin 
• 54081-47-9 Neoastilbin 

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.