(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

• ChemBase ID: 120137
• Molecular Formular: C21H18O11
• Molecular Mass: 446.36102
• Monoisotopic Mass: 446.0849114
• SMILES: [C@@H]1(O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)Oc1c(c(c2c(=O)cc(oc2c1)c1ccccc1)O)O)C(=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
• InChI: InChI=1S/C21H18O11/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)/t16-,17-,18+,19-,21+/m0/s1
• InChIKey: IKIIZLYTISPENI-ZFORQUDYSA-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
• IUPAC Traditional name: baicalin; (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
• Synonyms: (2S,3S,4S,5R,6S)-6-((5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid; Baicalein 7-glucuronoside; Baicaloside; Baicalein 7-O-glucuronide; 5,6-Dihydroxy-4-oxygen-2-phenyl-4H-1-benzopyran-7-beta-D-glucopyranose acid; Baicalin; Baicalein 7-O-β-D-glucuronide; Baicalin; 黄芩苷

Database IDs

• CAS Number: 21967-41-9
• MDL Number: MFCD00134418
• PubChem SID: 162214490; 24880654
• PubChem CID: 64982
• CHEBI ID: 2981
• CHEMBL: 485818
• Chemspider ID: 58507
• Unique Ingredient Identifier: 347Q89U4M5
• Wikipedia Title: Baicalin

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

• Apperance: solid
• Melting Point: 202 - 205°C; 202-205 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -85°, c = 1 in DMSO

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

Pharmacology Properties

• Gene Information: mouse ... Hexa(15211)
• Mechanism of Action: Prolyl endopeptidase inhibitor; affects the GABA receptors

Product Information

• Purity: 95%
• Biological Source: Isol. from Scutellaria spp., Oroxylum indicum and other plant spp.
• Application(s): Diuretic
• Empirical Formula (Hill Notation): C21H18O11

DETAILS

Sigma Aldrich - 572667

Packaging
1 g in glass bottle

REFERENCES

• The Flavonoids: Advances in Research since 1980, (Ed. Harborne, J.B.), Chapman and Hall, London, 1988