82475-03-4

Usage

Uses

Used in Pharmaceutical Industry:
Baicalin methyl ester is used as a therapeutic agent for treating neurodegenerative diseases, cancer, and inflammatory disorders due to its anti-inflammatory, antioxidant, and neuroprotective properties.
Used in Cosmetic Industry:
Baicalin methyl ester is used as an antioxidant ingredient in skincare and cosmetic products to protect the skin from oxidative stress and promote skin health.

Upstream product

• 67-56-1 methanol 
• 21967-41-9 baicalin 
• 13165-72-5 chlorosulfite de methyle 

Downstream Products

• 491-67-8 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one 
• 480-11-5 oroxylin A 
• 82475-02-3 5-hydroxy-6-methoxyflavone-7-O-β-D-glucuronide methyl ester 
• 29550-13-8 5,6-dihydroxy-7-methoxyflavone 
• 57396-78-8 Oroxin A 

Relevant academic research and scientific papers

An unambiguous and practical synthesis of Oroxylin A: a commonly misidentified flavone

Oroxylin A, a major flavonoid in the extracts of Oroxylum indicum as well as Scutellaria baicalensis possesses useful medicinal properties. Many of the published routes claiming the synthesis of Oroxylin A (1) have in fact led to a regioisomer Negletein that was misinterpreted as Oroxylin A. In the present work, we describe a novel, straight-forward and scalable semi-synthetic approach for rapid access to the title compound, the structure of which is unambiguously secured by NMR and X-ray crystallographic analysis of a derivative. This work also encompasses the synthesis of a glycosylated derivative of Oroxylin A viz OAGME (2), which has marked pharmacological importance.

PROCESS FOR SYNTHESIS OF OROXYLIN A

Disclosed is a novel, simple, scalable and environment friendly process for the synthesis of Oroxylin A from Baicalin. Baicalm is esterified to obtain a methyl ester which is further selectively methylated to provide Oroxylin A gluciironide methyl ester w

Crystal structures of the flavonoid Oroxylin A and the regioisomers Negletein and Wogonin

The flavonoid Oroxylin A (6-methoxychrysin or 5,7-dihydroxy-6-methoxy-2- phenyl-4H-chromen-4-one, C16H12O5) and its regioisomers are of increasing interest for a variety of bioactive functions and their pharmaceutical formulation is of importance. Previous difficulties in the separation and misidentification of Oroxylin A from its regioisomers Wogonin (8-methoxychrysin or 5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one) and Negletein (5,6- dihydroxy-7-methoxyflavone or 5,6-dihydroxy-7-methoxy-2-phenyl-4H-chromen- 4-one) render its full structural and powder X-ray characterization highly desirable. The low-temperature (100 K) crystal structures of Oroxylin A, Negletein and Wogonin sesquihydrate are reported for the first time. Wogonin crystallizes in two related but distinct hydrated forms. These have very similar powder diffractograms, indicating that such issues need to be addressed for its pharmaceutical formulation.

Process for synthesis of Oroxylin A

Disclosed is a novel, simple, scalable and environment friendly process for the synthesis of Oroxylin A from Baicalin. Baicalin is esterified to obtain a methyl ester which is further selectively methylated to provide Oroxylin A glucuronide methyl ester which on de-glycosylation results in the formation of Oroxylin A.

Baicalin derivative and application of baicalin and baicalin derivative in preparing drugs for treating bovine viral disease

The invention provides a baicalin derivative and an application of baicalin and baicalin derivative in preparing drugs for treating bovine viral disease and belongs to the technical field of medicines. According to the invention, the baicalin derivative u

An efficient, scalable approach to hydrolyze flavonoid glucuronides via activation of glycoside bond

Hydrolyzing flavonoid glucuronides into corresponding aglycones posed some significant challenges. To improve acid-catalyzed hydrolysis process of flavonoid glucuronide, structures of glucuronide, hydrolysis parameters and post-processing were optimized. The optimized condition was performed by hydrolysis flavonoid glycoside methyl ester in a mixed solvent consisting of 2?mol/L H2SO4/EtOH/H2O (1/8/1, v/v/v) at 95?°C for 7?h and resulted in up to 90% aglycone yields, minimal byproduct formations and milder hydrolysis conditions. Furthermore, the optimized method avoids tedious purification steps and is easily conducted on a relatively large-scale using economical and commercially available reagents.

The invention relates to a raw material for preparing the glucuronic acid the glucoside is corresponding aglycone (by machine translation)

The invention discloses a glucuronic acid the glucoside is raw material for preparing the corresponding aglycone method, comprises the following steps: (1), synthesis of methyl chlorine sulfurous acid; (2), glucuronic acid methyl ester glucoside synthesis; (3), the inorganic acid is added in the ethanol, into inorganic acid ethanol solution, and then the inorganic acid ethanol solution is added to step (2) is made in the product of the glucuronic acid methyl ester glucoside, acid hydrolysis; (4), after the reaction, the reaction is cooled down to the room temperature after the, in the reaction liquid is poured into the water, standing precipitate, precipitation after complete filtering, the resulting solid for recrystallization dilute alcohol, obtaining the corresponding aglycone pure product. The method of the invention essentially solves the problem of the glucuronic acid the glucoside is difficult hydrolysis, the process is simple, short reaction time, does not need to use a large amount of organic solvent, after treatment is simple, the resulting aglycone yield is as high as 90%, purity as high as 99%, low cost, can be used for large-scale industrial production. (by machine translation)

A convenient and efficient approach to synthesize negletein from baicalin

A simple two-step/one-pot and highly efficient strategy for the synthesis of negletein from naturally abundant and inexpensive baicalin has been developed. In this one-pot sequence, esterification of baicalin catalyzed by concentrated H2SO

Development of a concise synthetic approach to access oroxin A

A novel environment-friendly method to access bioactive oroxin A through a one-pot/two-step process from naturally abundant and inexpensive baicalin is described. The procedure presented here has several advantages including clean, one-pot, synthetic ease, and large-scale feasibility. This work also provides a model strategy for rapid and diverse access to natural molecules sharing the common skeleton of this family.

Nitrogen-containing flavonoid analogues as CDK1/cyclin B inhibitors: Synthesis, SAR analysis, and biological activity

A series of nitrogen-containing flavonoid analogues were designed and synthesized by Mannich reaction, and screened for the inhibitory activities of cyclin-dependent kinases using a FRET-based biochemical assay method. The results showed that C-8 nitrogen-containing baicalein analogues 3a-3f exhibited potent CDK1/Cyclin B inhibitory activities. 5,6,7-Trihydroxy-8-(dimethylaminomethyl)-2-phenyl-4H-chromen-4-one 3a, 5,6,7-trihydroxy-8-(pyrrolid inylmethyl)-2-phenyl-4H-chromen-4-one 3b, and 5,6,7-trihydroxy-8-(piperidinylmethyl)-2-phenyl-4H-chromen-4-one 3c (IC50 1.05-1.28 μM) were about sixfold more potent than baicalein 2 (IC50 6.53 μM). 5,6,7-Trihydroxy-8-(morpholinomethyl)-2-phenyl-4H-chromen-4-one 3d, 5,6,7-trihydroxy-8-(thiomorpholinomethy)-2-phenyl-4H-chrom en-4-one 3e, and 5,6,7-trihydroxy-8-(4-methylpiperazinylmethyl)-2-phenyl-4H-chromen-4-one 3f (IC50 0.27-0.38 μM) were about 20-fold more potent than baicalein, and were at the same level as flavopiridol (IC50 0.33 μM).