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

• ChemBase ID: 133678
• Molecular Formular: C15H16O7
• Molecular Mass: 308.28334
• Monoisotopic Mass: 308.08960285
• SMILES: c1cc(c(cc1[C@@H]1[C@H](Cc2c(cc(cc2O1)O)O)O)O)O.O
• Canonical SMILES: Oc1cc2O[C@H](c3ccc(c(c3)O)O)[C@H](Cc2c(c1)O)O.O
• InChI: InChI=1S/C15H14O6.H2O/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;1H2/t13-,15+;/m0./s1
• InChIKey: OFUMQWOJBVNKLR-NQQJLSKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol hydrate
• IUPAC Traditional name: (+)-catechol hydrate
• Synonyms: trans-3,3′,4′,5,7-Pentahydroxyflavane; trans-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol; (±)-Catechin hydrate; (+)-Catechin hydrate; (+)-Cyanidol-3; (2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol; 反式-3,3′,4′,5,7-五羟基黄烷; 反式-2-(3,4-二羟苯基)-3,4-二氢-1(2H)-苯并吡喃-3,5,7-三醇; (±)-儿茶精 水合物; (+)-儿茶精-3; (2R,3S)-2-(3,4-二羟基苯基)-3,4-二氢-1(2H)-苯并吡喃-3,5,7-三醇; (+)-儿茶素 水合物

Database IDs

• CAS Number: 225937-10-0; 7295-85-4
• EC Number: 205-825-1; 230-731-2
• MDL Number: MFCD00150865; MFCD00149354
• Beilstein Number: 3595244; 92762
• PubChem SID: 162227955; 24278298; 24853212
• PubChem CID: 107957

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: ethanol: soluble50 mg/mL
• Apperance: yellow to yellow with tan cast powder
• Melting Point: ~200 °C (dec.); 175-177 °C (anhydrous)(lit.)
• Optical Rotation: [α]/D +26±2°, c = 1 in H2O

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 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

Product Information

• Purity: ≥96.0% (HPLC); ≥96.0% (sum of enantiomers, HPLC); ≥98% (HPLC); ≥98.5% (HPLC)
• Grade: puriss.; purum
• Impurities: ≤8% water
• Empirical Formula (Hill Notation): C15H14O6 · xH2O

DETAILS

Sigma Aldrich - C1251

Biochem/physiol Actions
An antioxidant flavonoid of plant origin; a free radical scavenger, preventing free radical-mediated damage in a variety of biological systems. For example, at physiological pH catechin suppressed DNA strand breaks by hydroxyl radicals. It has also been shown to prevent human plasma oxidation. It delayed the consumption of endogenous lipid-soluble antioxidants and inhibited lipid oxidation.

Sigma Aldrich - 22110

Caution
loses water of hydration during storage
Packaging
1 g in glass bottle
10, 50 g in poly bottle

Sigma Aldrich - 41142

Biochem/physiol Actions
Polyphenolic antioxidant. Used in traditional Chinese medicine.

Sigma Aldrich - 22130

Biochem/physiol Actions
Polyphenolic antioxidant. Used in traditional Chinese medicine.