References of (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Title: Catechin
CAS Registry Number: 154-23-4
CAS Name: (2
R-
trans)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2
H-1-benzopyran-3,5,7-triol
Synonyms: catechol; 3,3¢,4¢,5,7-flavanpentol; catechinic acid; catechuic acid; (+)-cyanidanol-3; dexcyanidanol; cyanidol
Trademarks: Catergen (Zyma)
Molecular Formula: C15H14O6
Molecular Weight: 290.27
Percent Composition: C 62.07%, H 4.86%, O 33.07%
Literature References: Flavonoid found primarily in higher woody plants as (+)-catechin along with
(-)-epicatechin (
cis form). From catechu (gambir and acacia), mahogany wood, etc.: Perkin, Yoshitake,
J. Chem. Soc. 81, 1160 (1902); Freudenberg
et al., Ber. 55, 1734 (1922). Structure: Freudenberg
et al., Ann. 444, 135 (1925). Stereochemistry: Clark-Lewis,
Chem. Ind. (London) 1955, 1218; Hardegger
et al., Helv. Chim. Acta 40, 1819 (1957); Clark-Lewis,
J. Chem. Soc. 1960, 2433. Pharmacology: Van Cauwenberge
et al., C.R. Seances Soc. Biol. Ses Fil. 165, 1195 (1971). Metabolism: Das, Sothy,
Biochem. J. 125, 417 (1971); and absorption in human: N. P. Das,
Biochem. Pharmacol. 20, 3435 (1971). Biosynthesis of epicatechins: Zaprometov, Grisebach,
Z. Naturforsch. 28c, 113 (1973). Other catechins such as
afzelechin and
gallocatechin and catechin oligomers (
procyanidins) also exist in nature: Thompson
et al., J. Chem. Soc. Perkin Trans. 1 1972, 1287.
See also Bioflavonoids.
Properties: Needles from water + acetic acid, occurs as hydrate. mp 93-96°; 175-177° when anhydr. [a]D18 +16 to +18.4°.
Melting point: mp 93-96°; 175-177° when anhydr
Optical Rotation: [a]D18 +16 to +18.4°
Derivative Type: dl-Form
CAS Registry Number: 7295-85-4
Properties: Needles from water + acetic acid, mp 212-216°. Slightly sol in cold water, ether; sol in hot water, alcohol, glacial acetic acid, acetone. Practically insol in benzene, chloroform, petr ether.
Melting point: mp 212-216°
Derivative Type: l-Form
CAS Registry Number: 18829-70-4
Properties: Needles from water + acetic acid, mp 93-96°; 175-177° when anhydr. [a]D -16.8°.
Melting point: mp 93-96°; 175-177° when anhydr
Optical Rotation: [a]D -16.8°
NOTE: Catechin is also called catechol (flavan) to distinguish it from catechol (pyrocatechol,
q.v.).
Use: In dyeing and tanning.
Therap-Cat: Antidiarrheal.
Keywords: Antidiarrheal; Hepatoprotectant.