Baicalein Chemical Properties

Melting point:

256-271 °C (lit.)

Boiling point:

373.35°C (rough estimate)

Density 

1.3280 (rough estimate)

refractive index 

1.5000 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Yellow solid

pka

6.31±0.40(Predicted)

color 

Yellow or yellow-green

Merck 

14,942

BRN 

272683

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 week.

InChIKey

FXNFHKRTJBSTCS-UHFFFAOYSA-N

LogP

3.310 (est)

CAS DataBase Reference

491-67-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DJ3100898

Hazard Note 

Irritant

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Baicalein Usage And Synthesis

Description

Baicalein (491-67-8) is an inhibitor of protein tyrosine kinase in leukemia (CEM) cells. Induces cell cycle arrest and apoptosis.1?Originally reported as a selective inhibitor of 12-lipoxygenase, baicalein has since been shown to inhibit both 12-LO and 15-LO (IC50=0.64 μM for 12-LO and 1.6 μM for 15-LO).2 Baicalein displays anti-inflammatory activity and inhibits adjuvant-induced arthritis. Also inhibits prolyl oligopeptidase (IC50=36 μM).3

Chemical Properties

Yellow Crystalline Solid

Uses

Baicalein is a flavonoid originally isolated from the roots of Scutellaria baicalensis Georgi. Several different functions of baicalein have been reported. Platelet 12-lipoxygenase is inhibited by baicalein with an ID50 value of 0.12 μM, with minimal inhibition of platelet cyclooxygenase-1 (IC50 = 0.83 mM). Baicalein inhibits lipid peroxidation, as assessed by production of TBARS, with an IC50 value of 5 μM. In addition to these effects, baicalein may play a role in apoptosis, as the compound inhibits cell growth of three human hepatocellular carcinoma cell lines with IC50 values ranging from 17-70 μg/ml.

Uses

antiviral (HIV)

Uses

An inhibitor of 12-lipoxygenase, leukotriene biosynthesis and release of lysosomal enzymes. It also inhibits cellular Ca2+ uptake and mobilization and adjuvant-induced arthritis. Baicalein is the fl avonoid component of Nepalese and Sino-Japanese crude drugs.

Uses

inhibitor of lipoxidase and leukotriene biosynthesis

Uses

An inhibitor of Ca2+ uptake, 5-LO, and 12-LO

Definition

ChEBI: A trihydroxyflavone with the hydroxy groups at positions C-5, -6 and -7.

General Description

Baicalein, a flavonoid, is a xanthine oxidase inhibitor. Anti-inflammatory effects of baicalein in peripheral human leukocytes has been studied.

Biological Activity

Inhibitor of 5- and platelet 12-lipoxygenases (IC 50 values are 9.5 and 0.12 mM respectively). Also inhibits Raf-mediated MEK-1 phosphorylation in C6 rat glioma cells and induces G1 and G2 cell cycle arrest by decreasing cdk1, cdk2, cyclin D2 and cyclin A expression. Anti-inflammatory in vivo .

Biochem/physiol Actions

The flavonoid component of Nepalese and Sino-Japanese crude drugs. 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.

References

[1] HONG Z LEE. Baicalein induced cell cycle arrest and apoptosis in human lung squamous carcinoma CH27 cells.[J]. Anticancer research, 2005, 25 2A: 959-964.
[2] JOSHUA D. DESCHAMPS  Theodore R H  Victor A Kenyon. Baicalein is a potent in vitro inhibitor against both reticulocyte 15-human and platelet 12-human lipoxygenases[J]. Bioorganic & Medicinal Chemistry, 2006, 14 12: Pages 4295-4301. DOI:10.1016/j.bmc.2006.01.057
[3] TERESA TARRAGÓ . Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor[J]. Bioorganic & Medicinal Chemistry, 2008, 16 15: Pages 7516-7524. DOI:10.1016/j.bmc.2008.04.067

Baicalein(491-67-8)Related Product Information

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• ISOFLAVONES
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• EUPATORIN-5-METHYL ETHER
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