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Catechin
Catechin /ˈkætɪkɪn/ is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids.
The name of the catechin chemical family derives from catechu, which is the tannic juice or boiled extract of Mimosa catechu (Acacia catechu L.f.).
Catechin possesses two benzene rings (called the A and B rings) and a dihydropyran heterocycle (the C ring) with a hydroxyl group on carbon 3. The A ring is similar to a resorcinol moiety while the B ring is similar to a catechol moiety. There are two chiral centers on the molecule on carbons 2 and 3. Therefore, it has four diastereoisomers. Two of the isomers are in trans configuration and are called catechin and the other two are in cis configuration and are called epicatechin.
The most common catechin isomer is (+)-catechin. The other stereoisomer is (−)-catechin or ent-catechin. The most common epicatechin isomer is (−)-epicatechin (also known under the names L-epicatechin, epicatechol, (−)-epicatechol, L-acacatechin, L-epicatechol, epicatechin, 2,3-cis-epicatechin or (2R,3R)-(−)-epicatechin).
The different epimers can be separated using chiral column chromatography.
Making reference to no particular isomer, the molecule can just be called catechin. Mixtures of the different enantiomers can be called (±)-catechin or DL-catechin and (±)-epicatechin or DL-epicatechin.
Catechin and epicatechin are the building blocks of the proanthocyanidins, a type of condensed tannin.
Moreover, the flexibility of the C-ring allows for two conformation isomers, putting the B-ring either in a pseudoequatorial position (E conformer) or in a pseudoaxial position (A conformer). Studies confirmed that (+)-catechin adopts a mixture of A- and E-conformers in aqueous solution and their conformational equilibrium has been evaluated to be 33:67.
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Catechin AI simulator
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Catechin
Catechin /ˈkætɪkɪn/ is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids.
The name of the catechin chemical family derives from catechu, which is the tannic juice or boiled extract of Mimosa catechu (Acacia catechu L.f.).
Catechin possesses two benzene rings (called the A and B rings) and a dihydropyran heterocycle (the C ring) with a hydroxyl group on carbon 3. The A ring is similar to a resorcinol moiety while the B ring is similar to a catechol moiety. There are two chiral centers on the molecule on carbons 2 and 3. Therefore, it has four diastereoisomers. Two of the isomers are in trans configuration and are called catechin and the other two are in cis configuration and are called epicatechin.
The most common catechin isomer is (+)-catechin. The other stereoisomer is (−)-catechin or ent-catechin. The most common epicatechin isomer is (−)-epicatechin (also known under the names L-epicatechin, epicatechol, (−)-epicatechol, L-acacatechin, L-epicatechol, epicatechin, 2,3-cis-epicatechin or (2R,3R)-(−)-epicatechin).
The different epimers can be separated using chiral column chromatography.
Making reference to no particular isomer, the molecule can just be called catechin. Mixtures of the different enantiomers can be called (±)-catechin or DL-catechin and (±)-epicatechin or DL-epicatechin.
Catechin and epicatechin are the building blocks of the proanthocyanidins, a type of condensed tannin.
Moreover, the flexibility of the C-ring allows for two conformation isomers, putting the B-ring either in a pseudoequatorial position (E conformer) or in a pseudoaxial position (A conformer). Studies confirmed that (+)-catechin adopts a mixture of A- and E-conformers in aqueous solution and their conformational equilibrium has been evaluated to be 33:67.