Baicalin
[CAS# 21967-41-9]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Natural source anti-infectives
• Name: Baicalin
• Synonyms: Baicalein 7-O-glucuronide; 5,6-Dihydroxy-4-oxygen-2-phenyl-4H-1-benzopyran-7-beta-D-glucopyranose acid
• Molecular Formula: C₂₁H₁₈O₁₁
• Molecular Weight: 446.36
• CAS Registry Number: 21967-41-9
• EC Number: 606-866-1
• 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

Properties

• Melting point: 202-205 °C
• alpha: -85 ° (c=1, DMSO)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Baicalin is a flavonoid glycoside primarily found in the roots of Scutellaria baicalensis, a plant commonly used in traditional Chinese medicine. The compound has attracted significant attention due to its diverse biological activities and potential therapeutic applications. The discovery of baicalin dates back to ancient herbal medicine practices, with references to its use in traditional remedies for various ailments. Modern scientific investigations began in the mid-20th century, leading to the isolation and characterization of baicalin as a prominent bioactive compound within Scutellaria baicalensis.

The chemical structure of baicalin consists of a baicalein aglycone bound to a glucuronic acid moiety, resulting in its classification as a flavonoid glycoside. This unique structure contributes to its solubility and bioavailability, enhancing its potential for various therapeutic applications. The synthesis of baicalin can be achieved through extraction from natural sources or through semi-synthetic methods, which involve the glycosylation of baicalein. The extraction process often utilizes solvents such as ethanol or methanol to obtain a concentrated extract rich in baicalin and other flavonoids.

Baicalin is renowned for its extensive pharmacological properties, which have been the subject of numerous studies. One of its primary applications is in the field of anti-inflammatory therapy. Research has demonstrated that baicalin exhibits potent anti-inflammatory effects by inhibiting the production of pro-inflammatory cytokines and enzymes. These properties make baicalin a candidate for developing treatments for inflammatory conditions such as arthritis, asthma, and inflammatory bowel disease.

In addition to its anti-inflammatory effects, baicalin has garnered interest for its neuroprotective properties. Studies suggest that baicalin can protect neuronal cells from oxidative stress and apoptosis, making it a potential therapeutic agent for neurodegenerative diseases such as Alzheimer's and Parkinson's. Its ability to cross the blood-brain barrier further enhances its prospects in neuropharmacology.

Baicalin also displays significant antioxidant activity, which has implications for overall health and longevity. By scavenging free radicals and reducing oxidative stress, baicalin contributes to cellular health and may help prevent chronic diseases associated with oxidative damage, such as cardiovascular disease and cancer. These antioxidant properties have prompted investigations into baicalin's potential role as a dietary supplement or functional food ingredient.

Moreover, baicalin has shown promise in the field of anticancer research. In vitro and in vivo studies have indicated that baicalin can inhibit the proliferation of various cancer cell lines, including lung, breast, and liver cancer cells. Its mechanisms of action involve the induction of apoptosis and cell cycle arrest, making it a subject of interest for developing novel cancer therapies.

Recent advancements in nanotechnology have opened new avenues for enhancing the bioavailability and efficacy of baicalin. Nanocarrier systems, such as liposomes and nanoparticles, have been employed to improve the delivery of baicalin to target sites in the body, thereby enhancing its therapeutic effects. These innovations are paving the way for more effective formulations that can optimize the benefits of baicalin in clinical applications.

In summary, baicalin is a flavonoid glycoside with a rich history rooted in traditional medicine and a promising future in modern therapeutics. Its diverse biological activities, including anti-inflammatory, neuroprotective, antioxidant, and anticancer properties, make it a valuable compound in pharmaceutical research. As investigations continue to explore its full potential, baicalin is poised to play a significant role in the development of new therapies for various health conditions.

References

2000. Antioxidant and free radical scavenging effects of baicalein, baicalin and wogonin. Anticancer Research, 20(5B).
URL: pubmed.ncbi.nlm.nih.gov/11062694

2024. Supramolecular deep eutectic solvents in extraction processes: a review. Environmental Chemistry Letters, 22(5).
DOI: 10.1007/s10311-024-01795-3

2010. Comparative pharmacokinetics of baicalin and wogonoside by liquid chromatography-mass spectrometry after oral administration of Xiaochaihu Tang and Radix scutellariae extract to rats. Journal of Chromatography B, 878(22).
DOI: 10.1016/j.jchromb.2010.06.021