(-)-Epiafzelechin - ≥98% , CAS No.24808-04-6

CAS: 24808-04-6 Cat. No.: E697732 Molecular Weight: 274.27

GRADE & PURITY ≥98%

Synonyms

24808-04-6 | EPIAFZELECHIN (2R,3R)(-) | CHEBI:31028 | (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol | 2,3-cis-epiafzelechin | (2R,3R)-epiafzelechin | (2R,3R)-2-(4-hydroxyphenyl)chromane-3,5,7-triol | epiafzelechin | epi-Afzelechin | CHEM

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Overview

(-)-Epiafzelechin is a COX inhibitor with antioxidant and anti-inflammatory activity, osteoprotective effects in a mature ovariectomized mouse model, ability to stimulate osteoblast activity and inhibit osteoclast activity.

Specifications

Synonyms

24808-04-6 | EPIAFZELECHIN (2R, 3R)(-) | CHEBI:31028 | (2R, 3R)-2-(4-hydroxyphenyl)-3, 4-dihydro-2H-chromene-3, 5, 7-triol | 2, 3-cis-epiafzelechin | (2R, 3R)-epiafzelechin | (2R, 3R)-2-(4-hydroxyphenyl)chromane-3, 5, 7-triol | epiafzelechin | epi-Afzelechin | CHEM

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O
• IUPAC Name: (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• InChIKey: RSYUFYQTACJFML-UKRRQHHQSA-N
• INCHI: 1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1
• Isomeric SMILES: C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O
• Alternate CAS: 24808-04-6
• MeSH Entry Terms: (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol;afzelechin
• Molecular Weight: 274.27

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavans

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavans
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavan-3-ols
• Alternative Parents: 7-hydroxyflavonoids 5-hydroxyflavonoids 4'-hydroxyflavonoids 3-hydroxyflavonoids 1-benzopyrans 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: 3-hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavan-3-ol - Hydroxyflavonoid - 1-benzopyran - Chromane - Benzopyran - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Benzenoid - Monocyclic benzene moiety - Secondary alcohol - Polyol - Organoheterocyclic compound - Oxacycle - Ether - Hydrocarbon derivative - Organic oxygen compound - Alcohol - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.
• External Descriptors: Flavans, Flavanols and Leucoanthocyanidins

Data sources

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

Associated Targets(Human)

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

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

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

Discover Target: PTGS2

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H9 (1832 Activities)

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Liver (3974 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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

SYNJ2 Tchem Synaptojanin-2 (76 Activities)

Discover Target: SYNJ2

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Associated Targets(non-human)

Brugia malayi (1377 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Moisture sensitive, Light sensitive
• Molecular Weight: 274.270 g/mol
• XLogP3: 0.700
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 274.084 Da
• Monoisotopic Mass: 274.084 Da
• Topological Polar Surface Area: 90.200 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 328.000
• 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