(2R,3S)-catechin

Catechin

Names
IUPAC name (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
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
Identifiers
CAS Number	7295-85-4 (±) N 154-23-4 (+) N 18829-70-4 (-) N 88191-48-4 (+), hydrate N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15600 Y
ChemSpider	8711 Y
ECHA InfoCard	100.005.297
PubChem CID	9064
UNII	8R1V1STN48 Y
InChI InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1 Y Key: PFTAWBLQPZVEMU-DZGCQCFKSA-N Y InChI=1/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1 Key: PFTAWBLQPZVEMU-DZGCQCFKBX
SMILES Oc1ccc(cc1O)[C@H]3Oc2cc(O)cc(O)c2C[C@@H]3O
Properties
Chemical formula	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)	+14.0°
Hazards
Main hazards	Mutagenic for mammalian somatic cells, mutagenic for bacteria and yeast
Safety data sheet	sciencelab AppliChem
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26-S36
Lethal dose or concentration (LD, LC):
LD50 (median dose)	(+)-catechin : 10,000 mg/kg in rat (RTECS) 10,000 mg/kg in mouse 3,890 mg/kg in rat (other source)
Pharmacology
Routes of administration	Oral
Pharmacokinetics:
Excretion	Urines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Catechin /ˈkætɪtʃɪn/ 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).

The different epimers can be distinguished using chiral column chromatography.