Baicalin

Base Information

• Chemical Name: Baicalin
• CAS No.: 21967-41-9
• Molecular Formula: C21H18O11
• Molecular Weight: 446.367
• Hs Code.: 29329990
• European Community (EC) Number: 606-866-1,633-784-3
• UNII: 347Q89U4M5
• DSSTox Substance ID: DTXSID701346569
• Nikkaji Number: J94.473D
• Wikipedia: Baicalin
• Wikidata: Q2879368
• Metabolomics Workbench ID: 52991
• ChEMBL ID: CHEMBL485818
• Mol file: 21967-41-9.mol

Synonyms:7-D-glucuronic acid-5,6-dihydroxy-flavone;7-D-glucuronic acid-5,6-dihydroxyflavone;baicalin

Chemical Property of Baicalin

Chemical Property:

• Appearance/Colour: Yellow powder
• Vapor Pressure: 1.07E-29mmHg at 25°C
• Melting Point: 231-233 °C(lit.)
• Refractive Index: 1.739
• Boiling Point: 836.6 °C at 760 mmHg
• PKA: 2.72±0.70(Predicted)
• Flash Point: 297.2 °C
• PSA: 187.12000
• Density: 1.737 g/cm³
• LogP: 0.14220
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 446.08491139
• Heavy Atom Count: 32
• Complexity: 748

Purity/Quality:

80%,90% , ^*data from raw suppliers

Baicalin 7-b-D-glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O)O
• Description: Baicalin, the active compound of the Blue Skullcap, is a type of flavonoid. Baicalin exhibits anti-inflammatory, anti-tumor, anti-angiogenic, anti-oxidant, anti-apoptotic, anti-viral, and antibacterial properties. It could be used for the treatment of autoimmune diseases and several cancers (hepatitis B virus (HBV)-infected liver cancer,? hepatic cancer, cervical cancer, etc.). It can be used to treat against dengue virus. It is used in preparation of the drug for treating and rescuing ricin poisoning. Due to its anti-apoptotic effect which can protect PC-12 cells from oxidative stress, baicalin can be used for reducing stress and helping to promote healthy sleep cycles. Baicalin is a flavonoid that has been found in S. baicalensis and has diverse biological activities. It reduces myocardial apoptosis and increases cardiac microvessel levels of endothelial nitric oxide synthase (eNOS) in a rat model of ischemia-reperfusion injury when administered at doses of 30 and 100 mg/kg. Baicalin (50 and 80 mg/kg) increases the number of intratumor CD8+ T cells and reduces tumor volume in an H22 murine hepatocellular carcinoma model. It reduces LPS-induced cortical production of reactive oxygen species (ROS) and levels of IL-1β and TNF-α in a mouse model of neuroinflammation. Baicalin decreases body weight, increases the number of rats with regular estrous cycles, and ameliorates follicular development in a mouse model of dehydroepiandrosterone-induced polycystic ovary syndrome (PCOS). It also decreases immobility time in the forced swim test in a mouse model of depression induced by chronic mild stress. Baicalin is one of the main active ingredients obtained from the roots of huang qin (Scutellaria baicalensis Georgi). The Pharmacopoeia of the People’s Republic of China (2015) stipulates that the content of baicalin in radix scutellariae with dry goods shall not be less than 9.0%. The medicinal radix scutellariae distribution in China are now Yunnan radix scutellariae (S. amoena C.?H. Wright), sticky hairs radix scutellariae (S. viscidula Bunge), Gansu radix scutellariae (S. rehderiana Diels), Lijiang radix scutellariae (S. likiangensis Diels), Sichuan radix scutellariae (S. hypericifolia Lev l.), radix scutellariae (S. tenax W.?W. Smith var. patentipilosa G.? Y. Wu), etc., which contain a certain amount of baicalin. Radix scutellariae medicinal has a long history in China. Listed as goods in Shen Nong’s Classic of Materia Medica, it has been used clinically to treat diseases with symptoms such as “heat jaundice, intestinal dysentery, edema, amenorrhea, malignant sore, and scleritis” for about 2000? years. Scutellaria is recorded in the Pharmacopoeia of the People’s Republic of China to have the effects of “clear heat and wet, purging fire to detoxify, stop bleeding and tocolysis.” It is one of the commonly used traditional Chinese herbs, which is clinically used alone or with other Chinese medicine compatibility for the treatment of respiratory infections, acute dysentery, viral hepatitis, allergic disease and gynecological disease, and so on.
• Physical properties: Appearance: light yellow crystalline powder at room temperature. Solubility: insoluble in methanol, ethanol, and acetone; slightly soluble in chloroform and nitrobenzene; almost insoluble in water; soluble in hot acetic acid. Melting point: 202–205?°C.
• Uses: diuretic, prolyl endopeptidase inhibitor, antineoplastic Baicalin has been used in a study to examine its neuroprotective effect in chronically stressed rats.2
• Indications: Baicalin is mainly used for the adjuvant therapy of acute and chronic hepatitis and persistent hepatitis.
• Clinical Use: In clinical, baicalin is mainly used as the adjuvant therapy for acute and chronic hepatitis and persistent hepatitis. Baicalin was shown to reduce the expression of hepatitis B surface antigen, e antigen and the core antigen, and inhibited hepatitis B virus DNA replication. Reduced serum alanine aminotransferase level was observed in hepatitis patient treated with baicalin, and other liver function indexes were also found to be improved. No adverse reactions about baicalin have been reported. In addition, baicalin was reported to treat early diabetic nephropathy and alleviate the symptoms of diabetic neuropathyAs one of the antimicrobial components of Scutellaria baicalensis, eye drops containing 3% baicalin are used clinically in the treatment of trachoma, with the similar curative effect as rifampicin.Moreover, baicalein is used clinically for the treatment of enteritis and dysentery.

Technology Process of Baicalin

There total 9 articles about Baicalin 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:

C21H18O11*C42H70O35 (1178862-93-5) → baicalin (21967-41-9,27462-75-5,31564-28-0) + β‐cyclodextrin (7585-39-9)

Guidance literature:

In water; at 20 ℃; Equilibrium constant;

DOI:10.1016/j.saa.2009.03.025

Reference yield:

4-oxo-2-phenyl-4H-1-benzopyran-5,6,7-triyl triacetate (67047-05-6) → baicalin (21967-41-9,27462-75-5,31564-28-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / K₂CO₃, KI / acetone / 4 h / Heating

2: 60 percent / H₂ / Pd/C / acetone

3: 41 percent

With hydrogen; potassium carbonate; potassium iodide; palladium on activated charcoal; In acetone;

Reference yield:

7-(benzyloxy)-4-oxo-2-phenyl-4H-1-benzopyran-5,6-diyl diacetate (67047-06-7) → baicalin (21967-41-9,27462-75-5,31564-28-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / H₂ / Pd/C / acetone

2: 41 percent

With hydrogen; palladium on activated charcoal; In acetone;

upstream raw materials:

5,6-Diacetoxy-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsaeure-methylester)

5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one

UDP-glucuronic acid

4-oxo-2-phenyl-4H-1-benzopyran-5,6,7-triyl triacetate

Downstream raw materials:

5-hydroxy-6-methoxyflavone-7-O-β-D-glucuronide methyl ester

C₂₁H₁₈O₁₁*C₄₂H₇₀O₃₅

C₁₉H₁₅NO₈

5,6-Diacetoxy-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsaeure-methylester)

Refernces

• 1、 Nagashima, Shigeyuki,Hirotani, Masao,Yoshikawa, Takafumi. "Purification and characterization of UDP-glucuronate: Baicalein 7-O- glucuronosyltransferase from Scutellaria baicalensis Georgi. cell suspension cultures". . p. 533 - 538. Retrieved 2000.
• 2、 Mezey-Vandor, Gabriella,Farkas, Lorand,Kanzel, Ida,Nogradi, Mihaly. "Synthese von Baicalin und einiger anderer Baicalein-glycoside". . p. 1945 - 1949. Retrieved 2007/10/02.