Names | |
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IUPAC name
(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
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Other names
Cianidanol
Cyanidanol (+)-catechin D-Catechin Catechinic acid Catechuic acid Cianidol Dexcyanidanol (2R,3S)-Catechin 2,3-trans-catechin 3,3',4',5,7–flavanpentol |
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Identifiers | |
7295-85-4 (±) 154-23-4 (+) 18829-70-4 (-) 88191-48-4 (+), hydrate |
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3D model (Jmol) | Interactive image |
ChEBI | CHEBI:15600 |
ChEMBL | ChEMBL206452 |
ChemSpider | 8711 |
ECHA InfoCard | 100.005.297 |
PubChem | 9064 |
UNII | 8R1V1STN48 |
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Properties | |
C15H14O6 | |
Molar mass | 290.27 g·mol−1 |
Appearance | Colorless solid |
Melting point | 175 to 177 °C (347 to 351 °F; 448 to 450 K) |
UV-vis (λmax) | 276 nm |
Chiral rotation ([α]D)
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+14.0° |
Hazards | |
Main hazards | Mutagenic for mammalian somatic cells, mutagenic for bacteria and yeast |
Safety data sheet | sciencelab AppliChem |
R-phrases | R36/37/38 |
S-phrases | S26-S36 |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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(+)-catechin : 10,000 mg/kg in rat (RTECS) 10,000 mg/kg in mouse 3,890 mg/kg in rat (other source) |
Pharmacology | |
Oral | |
Pharmacokinetics: | |
Urines | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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what is ?) | (|
Infobox references | |
Catechin /ˈkætᵻtʃɪn/ is a flavan-3-ol, a type of natural phenol and antioxidant. It is a plant secondary metabolite. It belongs to the group of flavan-3-ols (or simply flavanols), part of the chemical family of 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 the (+)-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, epi-catechin, 2,3-cis-epicatechin or (2R,3R)-(-)-epicatechin).