(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

• ChemBase ID: 107335
• Molecular Formular: C15H14O6
• Molecular Mass: 290.26806
• Monoisotopic Mass: 290.07903817
• SMILES: O[C@@H]1Cc2c(O[C@@H]1c1ccc(O)c(O)c1)cc(O)cc2O
• Canonical SMILES: Oc1cc2O[C@H](c3ccc(c(c3)O)O)[C@@H](Cc2c(c1)O)O
• InChI: 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
• InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• IUPAC Traditional name: ent-epicatechin; (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• Synonyms: L-EPICATECHIN; (-)-cis-3,3′,4′,5,7-Pentahydroxyflavane; (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol; (-)-Epicatechin; (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; epi-Catechin; epi-Catechol; l-Acacatechin; l-Epicatechin; l-Epicatechol; (-)-Epicatechin; Epicatechol; Teacatechin I; Acacatechin; Kakaol; Colatein; Epicatechin; (-)-顺式-3,3′,4′,5,7-五羟基黄烷; (2R,3R)-2-(3,4-二羟基苯基)-3,4-二氢-1(2H)-苯并吡喃-3,5,7-三醇; (-)-表儿茶素

Database IDs

• CAS Number: 490-46-0
• EC Number: 207-710-1
• MDL Number: MFCD00075648
• Beilstein Number: 92760
• PubChem SID: 24894538; 162093204; 24874522; 24864472; 24894431
• PubChem CID: 72276

CALCULATED PROPERTIES

• Acid pKa: 9.004574
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 1.7949721
• LogD (pH = 7.4): 1.784451
• Log P: 1.795107
• Molar Refractivity: 73.9997 cm^3
• Polarizability: 28.420568 Å^3
• Polar Surface Area: 110.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Powder; White to Off-White Solid
• Melting Point: 234-237°C (dec.); 240 °C (dec.)(lit.); 240-245 °C (dec.)
• Optical Rotation: [α]20/D -54°, c = 1 in acetone: water (1:1); [α]20/D -56±3°, c = 1% in acetone: water (1:1)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• RTECS: KB3745000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... BACE1(23621), CYP1A2(1544)
• Mechanism of Action: Converts proinsulin to insulin; Modulator of erythrocyte membrane bound

Product Information

• Purity: ≥90% (HPLC); ≥90% (sum of enantiomers, HPLC); ≥95.0% (HPLC); ≥97.0% (HPLC); ≥98% (HPLC); 90%; 97%
• Grade: analytical standard; purum
• Biological Source: from green tea; Widespread in plants. First isol. in 1832 from Gambir-catechu (from Nauclea gambir) (most early isolates a mixt. of (+)-catechin and (?-epicatechin)
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antidiabetic; Antiinflammatory agent; Shows hepatotropic activity
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C15H14O6

DETAILS

MP Biomedicals - 05203364

MP Biomedicals Rare Chemical collection

Sigma Aldrich - E4018

Biochem/physiol Actions
Antioxidant found in chocolate.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Sigma Aldrich - E1753

Biochem/physiol Actions
Antioxidant
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 525952

Packaging
1 g in glass bottle

Sigma Aldrich - 39263

Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Toronto Research Chemicals - E582260

Potent antioxidant and antineoplastic agent.

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