5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one

• ChemBase ID: 72924
• Molecular Formular: C15H10O5
• Molecular Mass: 270.2369
• Monoisotopic Mass: 270.05282342
• SMILES: c1(c(c(c2c(c1)oc(cc2=O)c1ccccc1)O)O)O
• Canonical SMILES: Oc1cc2oc(cc(=O)c2c(c1O)O)c1ccccc1
• InChI: InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H
• InChIKey: FXNFHKRTJBSTCS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one
• IUPAC Traditional name: baicalein; 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one
• Synonyms: Baicalein; 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one; 5,6,7-Trihydroxyflavone; 5,6,7-Trihydroxyflavone; Baicalein; Baicalein; Noroxylin; 5,6,7-三羟基黄酮; 三羟黄酮; 5,6,7-三羟基黄酮

Database IDs

• CAS Number: 491-67-8
• MDL Number: MFCD00017459
• Beilstein Number: 272683
• Merck Index: 14942
• PubChem SID: 162037844; 24870246; 24847315
• PubChem CID: 5281605
• CHEBI ID: 2979
• CHEMBL: 8260
• Chemspider ID: 4444924
• Unique Ingredient Identifier: 49QAH60606
• Wikipedia Title: Baicalein

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 6.755033
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.6833563
• LogD (pH = 7.4): 1.9496312
• Log P: 2.7066891
• Molar Refractivity: 72.9139 cm^3
• Polarizability: 27.111025 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1

PROPERTIES

Physical Property

• Apperance: Yellow powder
• Melting Point: 256-271 °C(lit.); 268-270°C

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: mouse ... Hexa(15211)rat ... Alox15(81639), Alox5(25290)
• Mechanism of Action: ICAM 1 antagonist

Product Information

• Purity: ≥98.0% (UV); 97%; 98%; 98.0
• Salt Data: Free Base
• Biological Source: Isol. from Scutellaria spp. and other plants
• Application(s): Shows anti-HIV activity
• Empirical Formula (Hill Notation): C15H10O5

DETAILS

Selleck Chemicals - S2268

Research Area: Infection
Biological Activity:
Baicalein is a CYP2C9 and prolyl endopeptidase inhibitor. It is a flavone, a type of flavonoid, originally isolated from the roots of Scutellaria baicalensis. It is also reported in Oroxylum indicum or Indian trumpetflower. It is the aglycone of baicalin.The flavonoid has been shown to inhibit certain types of lipoxygenases and act as an anti-inflammatory agent. [1]References on Baicalein[1] http://en.wikipedia.org/wiki/Baicalein, ,

Sigma Aldrich - 465119

Biochem/physiol Actions
The flavonoid component of Nepalese and Sino-Japanese crude drugs.1,2 Baicalein, a major flavone of Scutellariae baicalensis, inhibits the 12-lipoxygenase (12-LOX) pathway of arachidonic acid metabolism, which inhibits cancer cell proliferation and induces apoptosis.
Packaging
100, 500 mg in glass bottle

Sigma Aldrich - 11712

Other Notes
Specific inhibitor of reverse transcriptase1; and 12-lipoxygenase2

REFERENCES

• http://en.wikipedia.org/wiki/Baicalein
• Kutney, J.P. et al., Phytochemistry, 1971, 10, 3298, (isol)
• Mezey-Vandor, G. et al., Chem. Ber., 1980, 113, 1945, (synth)
• Takahashi, H. et al., Bull. Chem. Soc. Jpn., 1987, 60, 2261, (isol)
• Stierle, D.B. et al., Phytochemistry, 1988, 27, 517, (isol, cmr)
• The Flavonoids: Advances in Research since 1980, (Ed. Harborne, J.B.), Chapman and Hall, London, 1988
• Ng, A.S. et al., J. Nat. Prod., 1990, 53, 747, (synth)
• Koh, L.L. et al., Acta Cryst. C, 1993, 49, 105, (cryst struct, derivs)
• Parmar, S.V. et al., Indian J. Chem., Sect. B, 1993, 32, 244, (synth, bibl)
• Liu, Q. et al., Phytochemistry, 1993, 32, 925; 34, 167, (derivs)
• Zhou, L. et al., CA, 1999, 130, 107543j, (Baicalein, activity)
• Rossi, M. et al., J. Nat. Prod., 2001, 64, 26-31, (uv, cryst struct)