(2S,3S,4S,5R,6S)-6-[(5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid hydrate

• ChemBase ID: 150174
• Molecular Formular: C21H20O12
• Molecular Mass: 464.3763
• Monoisotopic Mass: 464.09547608
• SMILES: c1ccc(cc1)c1cc(=O)c2c(o1)cc(c(c2O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O)O.O
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](Oc2cc3oc(cc(=O)c3c(c2O)O)c2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O.O
• InChI: InChI=1S/C21H18O11.H2O/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29;/h1-7,16-19,21,23-27H,(H,28,29);1H2/t16-,17-,18+,19-,21+;/m0./s1
• InChIKey: WLEKZZMZTPAGDD-ZSESPEEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid hydrate
• IUPAC Traditional name: baicalin hydrate
• Synonyms: Baicalein 7-β-D-glucopyranosiduronate; Baicalin hydrate; 贝加灵; 黄芩苷 水合物

Database IDs

• CAS Number: 206752-33-2
• MDL Number: MFCD00149302
• PubChem SID: 24863401; 162244335
• PubChem CID: 71311447

CALCULATED PROPERTIES

• Acid pKa: 2.6182277
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -2.0355527
• LogD (pH = 7.4): -2.76751
• Log P: 0.7588956
• Molar Refractivity: 104.9257 cm^3
• Polarizability: 40.821663 Å^3
• Polar Surface Area: 183.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 231-233 °C(lit.)
• Optical Rotation: [α]23/D -120°, c = 1 in 50% pyridine

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

Product Information

• Empirical Formula (Hill Notation): C21H18O11 · xH2O

DETAILS

Sigma Aldrich - 375756

Packaging
100, 500 mg in glass bottle
Application
The flavonoid component of Nepalese and Sino-Japanese crude drugs.1,2