Baicalein

Baicalein Basic information
Product Name:Baicalein
Synonyms:BAICALEIN(SH)NOW RG GRADE;Baicalein, monohydrate, 5,6,7-Trihydroxy-2-phenyl-4H-chromen-4-one monohydrate;Baicelein;Noroxylin;5,6,7-trihydroxy-2-phenyl-4H-chroMen-4-one;Baicalein 98%;5,6,7-trihydroxy-2-phenyl-4-chromenone hydrate;Baicaleine
CAS:491-67-8
MF:C15H10O5
MW:270.24
EINECS:000-000-0
Product Categories:API;Aromatics;Heterocycles;chemical reagent;pharmaceutical intermediate;phytochemical;Tri-substituted Flavones;The group of Scutellaria;Inhibitors;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product
Mol File:491-67-8.mol
Baicalein Structure
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
pka6.31±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.
InChIKeyFXNFHKRTJBSTCS-UHFFFAOYSA-N
LogP3.310 (est)
CAS DataBase Reference491-67-8(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 Information
ProviderLanguage
SigmaAldrich English
ALFA English
Baicalein Usage And Synthesis
DescriptionBaicalein (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 PropertiesYellow Crystalline Solid
UsesBaicalein 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.
Usesantiviral (HIV)
UsesAn 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.
Usesinhibitor of lipoxidase and leukotriene biosynthesis
UsesAn inhibitor of Ca2+ uptake, 5-LO, and 12-LO
DefinitionChEBI: A trihydroxyflavone with the hydroxy groups at positions C-5, -6 and -7.
General DescriptionBaicalein, a flavonoid, is a xanthine oxidase inhibitor. Anti-inflammatory effects of baicalein in peripheral human leukocytes has been studied.
Biological ActivityInhibitor 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 ActionsThe 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.
References1) Lee?et al. (2005),?Baicalein induced cell cycle arrest and apoptosis in human lung squamous carcinoma CH27 cells; Anticancer Res.,?25?959 2) Deschamps?et al. (2006),?Baicalein is a potent in vitro inhibitor against both reticulocyte 15-human and platelet 12-human lipoxygenases; Bioorg. Med. Chem.,?14?4295 3) Tarrago?et al. (2008),?Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor; Bioorg. Med. Chem.,?16?7516
Baicalein 6-METHOXYLUTEOLIN Emodin Baicalin Isoflavone Curcumin Riboflavin 5,6,7-TRIMETHOXYFLAVONE Wogonoside Theaflavin SCUTELLAREIN Wogonin Chrysin FLAVONE Scutellarin 7-HYDROXYFLAVONE EUPATORIN-5-METHYL ETHER ISOFLAVONES

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