• Name

  L-Epicatechin

• EINECS 207-710-1
• CAS No. 490-46-0
• Article Data62
• CAS DataBase
• Density 1.593g/cm³
• Solubility Soluble in water or alcohol
• Melting Point 240 °C (dec.)(lit.)
• Formula C15H14 O6
• Boiling Point 630.4 °C at 760 mmHg
• Molecular Weight 290.273
• Flash Point 335°C
• Transport Information
• Appearance White to light yellow crystal powder
• Safety S26;S36
• Risk Codes R36/37/38   
• Molecular Structure
• Hazard Symbols
• Synonyms 2H-1-Benzopyran-3,5,7-triol,2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-cis)-; Epicatechol, (-)- (8CI);(-)-(2R:3R)-5,7,3',4'-Tetrahydroxyflavan-3-ol; (-)-Epicatechin;(-)-Epicatechol; (2R,3R)-(-)-Epicatechin; Epicatechin; Epicatechol;L-Epicatechin; NSC 81161; epi-Catechin; epi-Catechol; l-Acacatechin;l-Epicatechin; l-Epicatechol
• PSA 110.38000
• LogP 1.54610

Synthetic route

154-23-4, 490-46-0, 7295-85-4, 13392-26-2, 17334-50-8, 18829-70-4, 35323-91-2, 72690-97-2

(+/-)-epicatechin

A

35323-91-2

(+)-epicatechin

B

490-46-0

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol

Conditions

Conditions	Yield
With CHIRAL PAKIC In ethanol; hexane at 20℃; Resolution of racemate;	A 85% B 84%
With CHIRAL PAK IC (250 X 4.6) mm, 5μ column In methanol at 25℃; Product distribution / selectivity; Resolution of racemate;
With CHIRAL PAK In methanol at 25℃; Resolution of racemate;

87292-49-7

5,7,3',4'-tetra-O-benzylepicatechin

490-46-0

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol

Conditions

Conditions	Yield
With 5% Pd(OH)2/C; hydrogen In tetrahydrofuran; methanol; water at 20℃; for 0.5h;	69%
With hydrogen; palladium(II) hydroxide In ethyl acetate at 20℃; for 40h;
With hydrogen; palladium(II) hydroxide In ethyl acetate at 20℃; for 40h;	0.010 mg

C50H42O6

A

490-46-0

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol

B

154-23-4

catechin

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol; ethyl acetate at 20 - 55℃;	A 55% B n/a

863-03-6, 10517-25-6, 13445-34-6, 17431-25-3, 20819-16-3, 25615-05-8, 130405-40-2, 1257-08-5

(-)-epicatechin gallate

A

(-)-(2R,3R,4R)-3,4,5,7,3',4'-hexahydroxyflavan

B

490-46-0

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol

Conditions

Conditions	Yield
With Diaporthe sp In methanol at 27℃; for 24h;	A 53% B 13%

20315-25-7

procyanidin B1

A

490-46-0

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol

B

154-23-4

catechin

Conditions

Conditions	Yield
With sodium cyanoborohydride In trifluoroacetic acid at 0℃; for 1h; Title compound not separated from byproducts;	A 21% B 20%

29106-49-8

procyanidin B2

490-46-0

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol

Conditions

Conditions	Yield
With hydrogenchloride for 0.5h; heating on a boiling water bath;
Multi-step reaction with 2 steps 1: ethanol / 1 h / boiling water bath 2: Raney nickel / ethanol / 2 h / Ambient temperature View Scheme

L-Epicatechin Chemical Properties

L-Epicatechin Toxicity Data With Reference

L-Epicatechin Safety Profile

L-Epicatechin Specification