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

• ChemBase ID: 108405
• 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+/m0/s1
• InChIKey: PFTAWBLQPZVEMU-DZGCQCFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• IUPAC Traditional name: (+)-catechol
• Synonyms: Catechin; (2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; (+)-(2R:3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol; (+)-Catechol; (+)-Cianidanol; (+)-Cyanidan-3-ol; (+)-Cyanidanol; (2R,3S)-(+)-Catechin; (+)-3-Cyanidanol; Biocatechin; Catechin; Catergen; Cyanidol; D-(+)-Catechin; HB-MC-TS 35; NSC 2819; P 70A; Teafuran 30A; Teafuran 30E; trans-(+)-3,3',4',5,7-Flavanpentol; (+)-Catechin; D-CATECHIN; Cianidanol; Cyanidanol; (+)-catechin; D-Catechin; Catechinic acid; Catechuic acid; Cianidol; Dexcyanidanol; (2R,3S)-Catechin; 2,3-trans-catechin; 3,3',4',5,7–flavanpentol; Catechin; (+)-Catechin; (2R,3S)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol; (+)-儿茶素

Database IDs

• CAS Number: 154-23-4; 7295-85-4
• EC Number: 205-825-1
• MDL Number: MFCD00075649
• PubChem SID: 162094454
• PubChem CID: 9064
• CHEBI ID: 15600
• CHEMBL: 251445
• Chemspider ID: 8711
• Unique Ingredient Identifier: 8R1V1STN48
• Wikipedia Title: Catechin

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; Methanmol
• Apperance: Colorless solid; Powder; Tan Solid
• Melting Point: 171-173°C; 175 - °C
• Optical Rotation: +14.0°
• Absorption Wavelength: 276 nm

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R36/37/38
• Safety Statements: 26; S26-S36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• Main Hazard: Mutagenic for mammalian somatic cells, mutagenic for bacteria and/or yeast
• LD50: (+)-catechin : 10,000 mg/kg in rat (RTECS); 10,000 mg/kg in mouse; 3,890 mg/kg in rat (other source)
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Urines

Product Information

• Purity: ≥99.0% (HPLC); 97%; 98%
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C15H14O6

DETAILS

MP Biomedicals - 05207242

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - C217500

(+)-Catechin is a flavonoid found primarily in higher woody plants as (+)-Catechin along with (-)-Epicatechin (cis form). Antidiarrheal.

REFERENCES

• Das, S., Biochem. J., et al.: 125, 417 (1971)
• Das, N.P., et al.: Biochem. Pharmacol., 20, 3435 (1971)