2545-00-8

Basic information

• Product Name: AFZELECHIN
• Synonyms: (2R)-2α-(4-Hydroxyphenyl)chroman-3β,5,7-triol;[2R,3S,(+)]-3,4-Dihydro-2-(4-hydroxyphenyl)-2H-1-benzopyran-3,5,7-triol
• CAS NO: 2545-00-8
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.26866
• Product Categories: Flavanones
• Mol File: 2545-00-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 252-254 °C (decomp)
• Boiling Point: 583.4°Cat760mmHg
• Flash Point: 306.6°C
• Appearance: /
• Density: 1.492g/cm³
• Vapor Pressure: 1.89E-14mmHg at 25°C
• Refractive Index: 1.708
• PKA: 9?+-.0.60(Predicted)
• CAS DataBase Reference: AFZELECHIN(CAS DataBase Reference)
• NIST Chemistry Reference: AFZELECHIN(2545-00-8)
• EPA Substance Registry System: AFZELECHIN(2545-00-8)

Safety Data

• Hazardous Substances Data: 2545-00-8(Hazardous Substances Data)

Usage

Definition

ChEBI: A tetrahydroxyflavan that is (2S)-flavan substituted by hydroxy groups at positions 3, 5, 7 and 4' respectively.

InChI:InChI=1/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2

Upstream product

• 126595-96-8 (-)-epiafzelechin 7-O-β-D-glucopyranoside 
• 251909-36-1 2,4,4',6-tetra-O-methoxymethyl-retro-chalcone 
• 251909-41-8 1-(4'-O-methoxymethylphenyl)-3-(2'',4'',6''-tri-O-methoxymethylphenyl)-1-propanol 
• 251909-46-3 (E)-1-(4'-O-methoxymethylphenyl)-3-(2'',4'',6''-tri-O-methoxymethylphenyl)-propene 
• 212265-19-5 2,4,6-tris(O-methoxymethyl)benzaldehyde 
• 85699-00-9 1-[4-(methoxymethoxy)phenyl]-1-ethanone 
• 84184-52-1 (E)-3-(4-(benzyloxy)phenyl)prop-2-en-1-ol 
• 773859-54-4 (+)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-ol 
• 251909-51-0 (1S,2S)-syn-1-(4'-O-methoxymethylphenyl)-3-(2'',4'',6''-tri-O-methoxymethylphenyl)-propane-1,2-diol 
• 142741-31-9 (+)-afzelechin-3-O-α-L-rhamnopyranoside 
• 114653-48-4 epiafzelechin-(4β->8)-epiafzelechin-(4β->8)-epiafzelechin 
• 114637-91-1 (2R,3R,4R,2'R,3'S,4'S)-4'-Benzylsulfanyl-2,2'-bis-(4-hydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-3,5,7,3',5',7'-hexaol 
• 114715-48-9 (-)-epi-afzlechin(4β->8)(-)-epi-afzelechin 
• 114715-49-0 (epi)afzelechin‐(4‐8)‐(epi)catechin 

Downstream Products

• 154-23-4 catechin 
• 114637-89-7 (2S)-7,4'-dihydroxyflavan-(4β->6)-epiafzelechin 
• 114715-51-4 (2S)-7,4'-dihydroxyflavan-(4α->6)-epiafzelechin 
• 114637-88-6 (2S)-7,4'-dihydroxyflavan-(4β->8)-epiafzelechin 
• 114715-50-3 (2S)-7,4'-dihydroxyflavan-(4α->8)-epiafzelechin 
• 67597-07-3 (2R)-3c,5,7-Triacetoxy-2r-(4-acetoxy-phenyl)-chroman 

Relevant articles and documents

General synthesis of epi-series catechins and their 3-gallates: Reverse polarity strategy

A general synthetic route to the epi-series catechins was developed based on the reverse polarity strategy. Aromatic nucleophilic substitution reaction followed by the sulfinyl-metal exchange and cyclization enabled stereo-controlled access to various members of epi-series catechins and their 3-gallates.

New oligomeric proanthocyanidine from Ziziphus jujuba

Chemical and spectral data establish the structure of an oligomeric proanthocyanidine PZ-5 isolated from Ziziphus jujuba.

(+)-AFZELECHIN 3-RHAMNOSIDE FROM CASSIPOUREA GERRARDII

A new flavanol glycoside has been isolated from the bark of Cassipourea gerrardii.Its structure has been established from spectroscopic and hydrolytic studies as (+)-afzelechin 3-O-α-L-rhamnopyranoside.Delayed homonuclear COSY studies show up interesting long-range couplings between specific protons. Key words: Cassipourea gerrardii; Rhizophoraceae; bark; (+)-afzelechin 3-O-α-L-rhamnopyranoside.