Baicalein

Base Information

• Chemical Name: Baicalein
• CAS No.: 491-67-8
• Molecular Formula: C15H10O5
• Molecular Weight: 270.241
• Hs Code.: 29329990
• Mol file: 491-67-8.mol

Synonyms:Baicalein(6CI);Flavone, 5,6,7-trihydroxy- (7CI,8CI);5,6,7-Trihydroxyflavone;NSC 661431;Noroxylin;

Chemical Property of Baicalein

Chemical Property:

• Appearance/Colour: Yellow crystalline solid
• Vapor Pressure: 8.55E-18mmHg at 25°C
• Melting Point: 256-271 °C(lit.)
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 575.932 °C at 760 mmHg
• PKA: 6.31±0.40(Predicted)
• Flash Point: 225.257 °C
• PSA: 90.90000
• Density: 1.548 g/cm³
• LogP: 2.57680
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Baicalein ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• 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
• 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. antiviral (HIV) 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. inhibitor of lipoxidase and leukotriene biosynthesis An inhibitor of Ca2+ uptake, 5-LO, and 12-LO

Technology Process of Baicalein

There total 52 articles about Baicalein which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

Baicalin methyl ester (82475-03-4) → 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one (491-67-8)

Guidance literature:

With sulfuric acid; In ethanol; water; at 95 ℃; for 8.5h; Inert atmosphere;

DOI:10.1016/j.tet.2017.02.039

Reference yield: 93.0%

baicalin (21967-41-9,27462-75-5,31564-28-0) → 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one (491-67-8)

Guidance literature:

With sulfuric acid; water; at 20 ℃; for 0.166667h;

DOI:10.3184/174751914X14017253941699

Reference yield: 92.0%

5,6,7-trimethoxyflavone (973-67-1) → 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one (491-67-8)

Guidance literature:

With hydrogen bromide; acetic acid; at 130 ℃;

DOI:10.1016/j.bmcl.2011.10.067

upstream raw materials:

6,7-dihydroxy-5-methoxyflavone

wogonin

7-hydroxy-5,8-dimethoxyflavone

5,6,7-trimethoxyflavone

Downstream raw materials:

baicalin

dihydrobaicalein

3-phenyl-1-(2,3,4,6-tetrahydroxyphenyl)-1-propanone

oroxylin A

Refernces

• 1、 Gella et al.. "-". . . Retrieved 1972.
• 2、 Chao, Jianbin,Su, Jian,Li, Jinxia,Zhao, Wei,Huang, Shuping,Du, Rui. "Investigation on the inclusion behaviour of baicalein with β-cyclodextrin and derivatives and their antioxidant ability study". . p. 644 - 653. Retrieved 2011.
• 3、 Hosozawa et al.. "-". . p. 2362. Retrieved 1972.
• 4、 -. "Flavonoid derivative as well as preparation method and identification method thereof". Paragraph 0078; 0079; 0080; 0088; 0100; 0110; 0120; 0129. . Retrieved 2019/02/17.
• 5、 Jiang, Xueyang,Zhou, Junting,Lin, Qinghua,Gong, Guiyi,Sun, Haopeng,Liu, Wenyuan,Guo, Qinglong,Feng, Feng,Qu, Wei. "Anti-angiogenic and anticancer effects of baicalein derivatives based on transgenic zebrafish model". supporting information. p. 4481 - 4492. Retrieved 2018/08/11.