(-)-Epicatechin

(-)-Epicatechin
Compound Structure:
Synonyms: (-)-Epicatechin; L-Epicatechin;(-)-Epicatechol;Epicatechol; (2R,3R)-(-)-Epicatechin;(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol; (-)-epi catechin; 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R)-);(2R-cis)-2-(3,4-Dihydroxyphenyl)-3,4
Compound ID: NMPC-009
PubChem ID:

72276
Molecular Formula: C15H14O6
Canonical SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O
InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N
About the compound:

Epicatechin is a flavan-3-ol, a type of flavonoid. Its chemical structure is similar to that of catechin, with the main difference being the stereochemistry of one hydroxyl group on the C-ring. Epicatechin is found in various foods and plants. Some notable sources include tea (especially green tea), cocoa, dark chocolate, apples, blackberries, and cherries. Epicatechin has been studied for a range of health-promoting effects. It's known to possess antioxidant properties, meaning it can neutralize harmful free radicals in the body. Additionally, research has explored its potential anti-inflammatory, cardioprotective, and neuroprotective effects. Consuming foods and beverages rich in epicatechin, like dark chocolate and green tea, can lead to potential health benefits. Notably, the health benefits of dark chocolate have often been attributed, in part, to its epicatechin content.

Safety and Hazard

GHS Hazard Statements        

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

290.27 g/mol

XLogP3

0.4

Hydrogen Bond Donor Count

5

Hydrogen Bond Acceptor Count

6

Rotatable Bond Count

1

Exact Mass

290.07903816 g/mol

Monoisotopic Mass

290.07903816 g/mol

Topological Polar Surface Area

110Ų

Heavy Atom Count

21

Formal Charge

0

Complexity

364

Isotope Atom Count

0

Defined Atom Stereocenter Count

2

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical appearance

Solid

Boiling Point

630.40 °C. @ 760.00 mm Hg (est)

Melting Point

240 °C

Solubility 

6.311e+004 mg/L @ 25 °C (est)

Source: PubChem
Source Species: Chrysophyllum albidum
Piliostigma thonningii.
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