E4018

(−)-Epicatechin

≥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
• Empirical Formula (Hill Notation): C₁₅H₁₄O₆
• CAS Number: 490-46-0
• Molecular Weight: 290.27
• Beilstein: 92760
• EC Number: 207-710-1
• MDL number: MFCD00075648
• UNSPSC Code: 12352205
• PubChem Substance ID: 24894538
• NACRES: NA.77

Properties

• biological source: green tea
• 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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: 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 Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves