Introduction：Basic information about Baicalein CAS 491-67-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 |
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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) |
| pka | 6.31±0.40(Predicted) |
| form | Yellow solid |
| 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. |
| 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 |
| SMILES | Oc1cc2OC(=CC(=O)c2c(O)c1O)c3ccccc3 |
| 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 |
| Storage Class | 11 - Combustible Solids |
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 flavonoid 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 Preparation Products And Raw materials
| Raw materials | 4H-1-Benzopyran-4-one, 6-hydroxy-5,7-dimethoxy-2-phenyl--->4H-1-Benzopyran-4-one, 5,6,7-tris(acetyloxy)-2-phenyl--->5,6,7-TRIMETHOXYFLAVONE-->Baicalin methyl ester-->Baicalin-->5,6-DIHYDROXY-7-METHOXYFLAVONE |
| Preparation Products | Oroxylin A |
