24808-04-6

Basic information

• Product Name: (-)-Epiafzelechin
• Synonyms: (2R,3R)-2-(4-Hydroxyphenyl)-3,5,7-chromantriol;(2R,3R)-3,4-Dihydro-2-(4-hydroxyphenyl)-2H-1-benzopyran-3,5,7-triol;[2R,(-)]-3,4-Dihydro-2α-(4-hydroxyphenyl)-2H-1-benzopyran-3α,5,7-triol
• CAS NO: 24808-04-6
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27
• Mol File: 24808-04-6.mol

Chemical Properties

• Melting Point: 241 °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: (-)-Epiafzelechin(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Epiafzelechin(24808-04-6)
• EPA Substance Registry System: (-)-Epiafzelechin(24808-04-6)

Safety Data

• Hazardous Substances Data: 24808-04-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
(-)-Epiafzelechin is used as a therapeutic agent for its antioxidant and anti-inflammatory properties. It helps in the treatment and prevention of various diseases, including cardiovascular diseases, neurodegenerative disorders, and certain types of cancer, by neutralizing free radicals and reducing inflammation.
Used in Food Industry:
(-)-Epiafzelechin is used as a natural additive in the food industry to enhance the nutritional value and health benefits of products. Its antioxidant properties help in preserving the freshness and quality of food items, while its anti-inflammatory effects contribute to the overall health benefits of consuming these products.
Used in Antioxidant Supplements:
(-)-Epiafzelechin is used as an ingredient in antioxidant supplements due to its potent antioxidant properties. These supplements are designed to support overall health and well-being by combating oxidative stress and promoting a healthy immune system.
Used in Cosmetics:
(-)-Epiafzelechin is used as an active ingredient in cosmetics, particularly in anti-aging and skin care products. Its antioxidant and anti-inflammatory properties help in reducing the signs of aging, promoting skin health, and protecting the skin from environmental stressors.

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/t13-,15-/m1/s1

Upstream product

• 114637-90-0 (2S)-7,4'-dihydroxyflavan-(4β->8)-epiafzelechin-(4β->8)-epiafzelechin 
• 84184-52-1 (E)-3-(4-(benzyloxy)phenyl)prop-2-en-1-ol 
• 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 
• 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 
• 773859-57-7 (+)-(2R)-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-one 
• 773859-52-2 (E)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-(4-benzyloxyphenyl)propene 
• 773859-58-8 (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-ol 
• 251909-61-2 (1R,2R)-syn-1-(4'-O-methoxymethylphenyl)-3-(2'',4'',6''-tri-O-methoxymethylphenyl)-propane-1,2-diol 
• 100-53-8 phenylmethanethiol 
• 114653-48-4 epiafzelechin-(4β->8)-epiafzelechin-(4β->8)-epiafzelechin 

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.

Enantioselective synthesis of afzelechin and epiafzelechin

The flavonoids afzelechin and epiafzelechin as well as their gallate esters were synthesized enantioselectively via Sharpless hydroxylation followed by regioselective cyclization. Graphical Abstract

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.

Tannins and Related Compounds. LXI. Isolation and Structures of Novel Bi- and Triflavanoids from the Leaves of Cassia fistula L.

Together with (-)-epiafzelechin (1) and its 3-O-glucoside (4), (-)-epicatechin (2) and procyanidin B-2 (3), seven new biflavanoids (5-7, 9-12) and two triflavanoids (8, 13) have been isolated from the leaves of Cassia fistula L. (Leguminosae).On the basis of chemical and spectroscopic evidence, the structures of 5-8 were established to be proanthocyanidins each having (-)-epiafzelechin unit(s) in the molecule, while 9-13 were shown to consist of (2S)-7,4'-dihydroxyflavan and (-)-epiafzelechin units.Keywords - Cassia fistula; Leguminosae; proanthocyanidin; flavan-3-ol glucoside; flavan-3-ol; flavan; condensed tannin; thiolytic degradation; acid-catalyzed condensation

Tannins and Related Compounds. LVI. Isolation of Four New Acylated Flavan-3-ols from Oolong Tea. (1)

A chemical examination of the aqueous acetone extract of commercial oolong tea has led to the isolation of four new acylated flavan-3-ols 1-4, together with the known compounds 5-13.On the basis of chemical and spectroscopic evidence, compounds 1-4 have been characterized as (-)-epiafzelechin 3-O-gallate (1), (-)-epicatechin 3-O-(4-O-methyl)-gallate (2), (-)-epicatechin 3-O-p-hydroxybenzoate (3) and (-)-epigallocatechin 3-O-cinnamate (4).

(-)-EPIAFZELECHIN 5-O-β-D-GLUCOSIDE FROM CRATAEVA RELIGIOSA

Epiafzelechin 5-glucoside was characterized from the bark of Crataeva religiosa together with other known compounds. - Key Word Index: Crataeva religiosa; Capparidaceae; flavan-3-ols; (-)-epiafzelechin 5-O-β-D-glucoside.