Baicalin

Baicalin

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Baicalin
Category Enzyme inhibitors
Catalog number BBF-03753
CAS 21967-41-9
Molecular Weight 446.36
Molecular Formula C21H18O11
Purity 90%

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BBF-03753 50 g $249 In stock

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Description

Baicalin is a flavone found in several species in the genus Scutellaria, including Scutellaria baicalensis and Scutellaria lateriflora. Baicalin is a positive allosteric modulator of the benzodiazepine site and/or a non-benzodiazepine site of the GABA receptor. Baicalin can also absorb ultraviolet rays, scavenge oxygen free radicals, and inhibit the production of melanin. Therefore, it can be used in medicine and cosmetics. It is a good functional cosmetic raw material.

Specification

Related CAS 27462-75-5 (Deleted CAS) 31564-28-0 (Deleted CAS) 100647-26-5 (Deleted CAS) 912850-49-8 (Deleted CAS) 206752-33-2 (hydrate)
Synonyms β-D-Glucopyranosiduronic acid, 5,6-dihydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl; 5,6-Dihydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl β-D-glucopyranosiduronic acid; Baicalein 7-glucuronide; Baicalein 7-O-glucuronide; Baicalein 7-O-β-D-glucuronide; (2S,3S,4S,5R,6S)-6-((5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
Storage Store at -20°C
IUPAC Name (2S,3S,4S,5R,6S)-6-(5,6-dihydroxy-4-oxo-2-phenylchromen-7-yl)oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
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
InChI InChI=1S/C21H18O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21,23-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1
InChI Key IKIIZLYTISPENI-ZFORQUDYSA-N

Properties

Appearance Yellow Solid
Boiling Point 836.6±65.0°C at 760 mmHg
Melting Point 223°C
Flash Point 297.2°C
Density 1.737±0.06 g/cm3
Solubility Soluble in DMSO (Slightly), Methanol (Slightly), Water

Reference Reading

1.Computational Approach Towards Exploring Potential Anti-Chikungunya Activity of Selected Flavonoids.
Seyedi SS1, Shukri M1, Hassandarvish P1, Oo A1, Muthu SE1, Abubakar S1, Zandi K1. Sci Rep. 2016 Apr 13;6:24027. doi: 10.1038/srep24027.
Chikungunya virus (CHIKV) is a mosquito-borne alphavirus that causes chikungunya infection in humans. Despite the widespread distribution of CHIKV, no antiviral medication or vaccine is available against this virus. Therefore, it is crucial to find an effective compound to combat CHIKV. We aimed to predict the possible interactions between non-structural protein 3 (nsP) of CHIKV as one of the most important viral elements in CHIKV intracellular replication and 3 potential flavonoids using a computational approach. The 3-dimensional structure of nsP3 was retrieved from the Protein Data Bank, prepared and, using AutoDock Vina, docked with baicalin, naringenin and quercetagetin as ligands. The first-rated ligand with the strongest binding affinity towards the targeted protein was determined based on the minimum binding energy. Further analysis was conducted to identify both the active site of the protein that reacts with the tested ligands and all of the existing intermolecular bonds.
2.Baicalin inhibits toll-like receptor 2/4 expression and downstream signaling in rat experimental periodontitis.
Sun JY1, Li DL2, Dong Y3, Zhu CH1, Liu J1, Li JD4, Zhou T5, Gou JZ1, Li A6, Zang WJ7. Int Immunopharmacol. 2016 Apr 21;36:86-93. doi: 10.1016/j.intimp.2016.04.012. [Epub ahead of print]
Periodontitis is a severe inflammatory response, leading to characteristic periodontal soft tissue destruction and alveolar bone resorption. Baicalin possesses potent anti-inflammatory activity; however, it is still unclear whether baicalin regulates toll-like receptor (TLR) 2/4 expression and downstream signaling during the process of periodontitis. In this study, the cervical area of the maxillary second molars of rats was ligated and inoculated with Porphyromonas gingivalis (P. gingivalis) for 4weeks to induce periodontitis. Some rats with periodontitis were treated intragastrically with baicalin (50, 100 or 200mg/kg/day) or vehicle for 4weeks. Compared with the sham group, the levels of TLR2, TLR4 and MyD88 expression and the p38 MAPK and NF-κB activation were up-regulated in the experimental periodontitis group (EPG), accompanied by marked alveolar bone loss and severe inflammation. Treatment with 100 or 200mg/kg/day baicalin dramatically reduced the alveolar bone loss, the levels of HMGB1, TNF-α, IL-1β, and MPO expression, and the numbers of inflammatory infiltrates in the gingival tissues.
3.Baicalin ameliorates experimental inflammatory bowel disease through polarization of macrophages to an M2 phenotype.
Zhu W1, Jin Z2, Yu J2, Liang J3, Yang Q4, Li F1, Shi X1, Zhu X5, Zhang X6. Int Immunopharmacol. 2016 Jun;35:119-26. doi: 10.1016/j.intimp.2016.03.030. Epub 2016 Apr 16.
Inflammatory bowel diseases (IBDs) are chronic inflammatory disorders of the intestinal tract. Baicalin, originally isolated from the root of the Chinese herb Huangqin (Scutellaria baicalensis Georgi) and its main active ingredient, has a protective effect against inflammatory responses in several diseases. The present study investigated the effects of baicalin on macrophage polarization and its therapeutic role in IBD. Murine peritoneal macrophages and mice with colitis were treated with baicalin. Macrophage subset distribution, M1 and M2 macrophage-associated mRNA expression, and interferon regulatory factor 4 and 5 (IRF4 and IRF5) expression were analyzed. siRNA transfection into mouse peritoneal macrophages was utilized to suppress IRF4. Fluorescence-activated cell sorting, western blot, and real-time PCR analyses were performed. Baicalin (50μM) limited lipopolysaccharide (LPS)-induced M1 macrophage polarization; decreased LPS-induced tumor necrosis factor α, interleukin (IL)-23, and IRF5 expression; and increased IL-10, arginase-1 (Arg-1), and IRF4 expression.
4.Baicalin Activates Glycine and [Formula: see text]-Aminobutyric Acid Receptors on Substantia Gelatinosa Neurons of the Trigeminal Subsnucleus Caudalis in Juvenile Mice.
Yin H1, Bhattarai JP1, Oh SM1, Park SJ1, Ahn DK2, Han SK1. Am J Chin Med. 2016 Apr;44(2):389-400. doi: 10.1142/S0192415X16500221.
The substantia gelatinosa (SG) of the trigeminal subnucleus caudalis (Vc) receives nociceptive afferent inputs from thin-myelinated A[Formula: see text] fibers and unmyelinated C fibers and has been shown to be involved in the processing of orofacial nociceptive information. Scutellaria baicalensis Georgi (Huang-Qin, SbG), one of the 50 fundamental herbs of Chinese herbology, has been used historically as anti-inflammatory and antineoplastic medicine. Baicalin, one of the major compounds of SbG, has been reported to have neuroprotective, anti-inflammatory and analgesic effects. However, the receptor type activated by baicalin and its precise action mechanism on the SG neurons of Vc have not yet been studied. The whole-cell patch clamp technique was performed to examine the ion channels activated by baicalin on the SG neurons of Vc. In high Cl[Formula: see text] pipette solution, the baicalin (300[Formula: see text][Formula: see text]M) induced repeatable inward currents ([Formula: see text][Formula: see text]pA, [Formula: see text]) without desensitization on all the SG neurons tested.

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