Epicatechin is a flavanol. Cacao products are rich in epicatechin. Epicatechin enhances the skeletal muscle structure in heart failure patients and minimises the cardiometabolic risks. It can be used for treating sarcopenia. Epicatechin reduces myostatin and β-galactosidase and increases the level of markers of muscle growth.
Antioxidant found in chocolate.

Product description：

(-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. (-)-Epicatechin inhibits the IL-1β-induced expression of iNOS by blocking the nuclear localization of the p65 subunit of NF-κB.

Application：

(−)-Epicatechin (EC) has been used:

as an antioxidant to downregulate nicotinamide adenine dinucleotide phosphate hydrogen (NADPH) oxidase and improve insulin sensitivity in in vivo (high fat-fed mice) and in vitro (HepG2 cells) studies

to study its effect on blood pressure, nitric oxide synthase (NOS) activity and anxiety-like behavior on borderline hypertensive rat (BHR) models

to test its effect on neuronal survival in the hippocampus of middle-aged rats on swimming training, under oxidative stress

to study its antioxidant activity in dark chocolate

as a characteristic compound in polyphenols analysis

仕様

同義語

仕様と純度

Moligand™, ≥97%(HPLC)

生化学的・生理学的メカニズム

Epicatechin enhances the skeletal muscle structure in heart failure patients and minimizes cardiometabolic risks. It can be used for treating sarcopenia. Epicatechin reduces myostatin and β-galactosidase and increases the level of markers of muscle growth

ソース

Tea

保管条件

Store at 2-8°C,Argon charged

入荷

Wet ice

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

等級

Moligand™

純度

≥97%(HPLC)

名前と識別子

パブケム・シド

488184683

パブケム・シド・ウル

https://pubchem.ncbi.nlm.nih.gov/substance/488184683

カノニカル・スマイル

C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol

InChIKey

PFTAWBLQPZVEMU-UKRRQHHQSA-N

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

異性体SMILES

C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O

WGKドイツ

RTECS

KB3745000

代替CAS番号

490-46-0,17334-50-8

MeSH用語

(+)-Catechin;(+)-Cyanidanol;(+)-Cyanidanol-3;(-)-Epicatechin;(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol;2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-cis)-;3,3',4',5,7-Flavanpentol;Catechin;Catechinic Acid;Catechuic Acid;

分子量

290.27

Beilstein

92760

Reaxy-Rn

6069926

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6069926&ln=

ドキュメント

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詳細データ

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Phenylpropanoids and polyketides
  - 分類 Flavonoids
    - Subclass Flavans
      - Level5 Flavan-3-ols
        Level6 Catechins

Kingdom	Organic compounds
Superclass	Phenylpropanoids and polyketides
分類	Flavonoids
Subclass	Flavans
Intermediate Tree Nodes	Flavan-3-ols
Direct Parent	Catechins
Alternative Parents	7-hydroxyflavonoids 5-hydroxyflavonoids 4'-hydroxyflavonoids 3-hydroxyflavonoids 3'-hydroxyflavonoids 1-benzopyrans Catechols Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Secondary alcohols Polyols Oxacyclic compounds Hydrocarbon derivatives
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	Catechin - 3'-hydroxyflavonoid - 3-hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Hydroxyflavonoid - Chromane - Benzopyran - 1-benzopyran - Catechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Benzenoid - Monocyclic benzene moiety - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Polyol - Ether - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
説明	This compound belongs to the class of organic compounds known as catechins. These are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol.
External Descriptors	Flavans, Flavanols and Leucoanthocyanidins
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61. DOI: 10.1186/s13321-016-0174-y

3 D構造

関連ターゲット（非人間）

pol Human immunodeficiency virus type 1 protease (9113 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

blaZ Beta-lactamase (285 Activities)

Discover Target: blaZ

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTSL Cathepsin L (58 Activities)

Discover Target: CTSL

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Galc Galactocerebrosidase (11 Activities)

Discover Target: Galc

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

Discover Target: Pkm

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Iap Intestinal alkaline phosphatase (419 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Salmonella paratyphi (588 Activities)

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溶解度	Soluble in acetone:water (1:1, 10 mg/ml), DMSO (100 mM), methanol, DMF (~12.5 mg/ml), and water (partly)., Soluble in acetone:water (1:1, 10 mg/ml), DMSO (100 mM), methanol, DMF (~12.5 mg/ml), and water (partly).,
感度	heat & air sensitive
比旋光度［α］	-62° (C=0.1,MeOH)
融点（°C）	240°C
分子量	290.270 g/mol
XLogP3	0.400
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	1
Exact Mass	290.079 Da
Monoisotopic Mass	290.079 Da
Topological Polar Surface Area	110.000 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	364.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	0
Covalently-Bonded Unit Count	1

(-)-Epicatechin - Moligand™, ≥97%(HPLC) , CAS No.490-46-0

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