2545-00-8

Usage

Uses

Used in Pharmaceutical Industry:
AFZELECHIN is used as a pharmaceutical compound for its potential therapeutic properties. Its hydroxy-substituted structure allows for interactions with various biological targets, making it a candidate for the development of new drugs.
Used in Cosmetic Industry:
AFZELECHIN is used as an active ingredient in cosmetics for its antioxidant and skin-protective properties. Its ability to scavenge free radicals and protect the skin from environmental stressors makes it a valuable component in skincare products.
Used in Food Industry:
AFZELECHIN is used as a natural food additive for its antioxidant and preservative properties. Its ability to extend the shelf life of food products and maintain their quality makes it a beneficial component in the food industry.
Used in Nutraceutical Industry:
AFZELECHIN is used as a nutraceutical ingredient for its potential health benefits. Its antioxidant and anti-inflammatory properties make it a promising candidate for the development of dietary supplements and functional foods.

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

• 108907-43-3 epi-Afzelechin gallate 
• 114637-87-5 (-)-epi-afzelachin 3-O-β-D-glucopyranoside 
• 114715-49-0 (epi)afzelechin‐(4‐8)‐(epi)catechin 
• 114715-48-9 (-)-epi-afzlechin(4β->8)(-)-epi-afzelechin 
• 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 

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 academic research and scientific papers

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.