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E4018

(−)-Epicatechin

Name: (−)-Epicatechin
Brand: SIGMA

≥98% (HPLC), from green tea

Synonym(s):

(−)-cis-3,3′,4′,5,7-Pentahydroxyflavane, (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₄O₆

CAS Number:

490-46-0

Molecular Weight:

290.27

UNSPSC Code:

12352205

NACRES:

NA.77

PubChem Substance ID:

24894538

EC Number:

207-710-1

Beilstein/REAXYS Number:

92760

MDL number:

MFCD00075648

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Properties

biological source

green tea

Quality Level

200

assay

≥98% (HPLC)

mp

240 °C (dec.) (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3ccc(O)c(O)c3

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-/m1/s1

InChI key

PFTAWBLQPZVEMU-UKRRQHHQSA-N

Gene Information

human ... BACE1(23621), CYP1A2(1544)

Description

General description

Epicatechin is a flavanol, that belongs to the class of secondary, polyphenolic plant metabolites.

Application

(-)-Epicatechin has been used:

to examine its biological effects in cell lines from human gender-specific cancers
to study its antiviral activity
to test its ability to regenerate this enzymatic activity both in vitro at the isolated MPO−H₂O₂−Cl- system and ex vivo in human polymorphonuclear leukocytes (PMNs)

Biochem/physiol Actions

This antioxidant is found in chocolate. (-)-Epicatechin is linked with cardiovascular effects. It is considered as a dependable standard due to its availability in cacao seeds and cocoa products. The halogenating activity of myeloperoxidase can be restored by (-)-epicatechin.

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pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Divergent antiviral effects of bioflavonoids on the hepatitis C virus life cycle

Khachatoorian R, et al.

Virology, 346-355 (2012)

Fluorescent detection of (-)-epicatechin in microsamples from cacao seeds and cocoa products: Comparison with Folin-Ciocalteu method

Ramirez-Sanchez I, et al.

Journal of Food Lipids, 23(8), 790-793 (2010)

Epicatechins purified from green tea (Camellia sinensis) differentially suppress growth of gender-dependent human cancer cell lines

Ravindranath M H, et al.

Evidence-Based Complementary and Alternative Medicine : ECAM, 3(2), 237-247 (2006)

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