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Chemical Structure| 491-67-8 Chemical Structure| 491-67-8

Structure of Baicalein
CAS No.: 491-67-8

Chemical Structure| 491-67-8

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Baicalein is a CYP2C9 and prolyl endopeptidase inhibitor.

Synonyms: 5,6,7-Trihydroxyflavone

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Product Citations

Product Citations

Beata Gąsowska-Bajger ; Hubert Wojtasek ;

Abstract: Baicalein (5,6,7-trihydroxyflavone) has been previously described as an inhibitor of tyrosinase (Guo et al. Int. J. Biol. Macromol. 118 (2018) 57–68). However, long before this article was published this flavonoid had been shown to be a substrate of this enzyme and a catecholic cofactor partially abolishing the lag-phase during oxidation of l-tyrosine. Other compounds with a 1,2,3-triphenol moiety, such as pyrogallol, gallic acid and its esters are also oxidized by tyrosinase. Gallic acid was also shown to reduce tyrosinase-generated o-quinones. We have demonstrated that baicalein is also rapidly oxidized by o-quinones generated from catechols by tyrosinase or by treatment with sodium periodate. Smaller changes of absorbance at 475 nm during oxidation of l-dopa by tyrosinase in the presence of baicalein do not result from enzyme inhibition but from reduction of dopaquinone by baicalein. This reaction prevents formation of dopachrome giving an effect of inhibition, which is only apparent. The actual reaction rates did not decrease but increased in the presence of baicalein, which we demonstrated by measurements of oxygen consumption.

Keywords: Tyrosinase ; Baicalein ; Flavonoid

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Product Details of Baicalein

CAS No. :491-67-8
Formula : C15H10O5
M.W : 270.24
SMILES Code : O=C(C1=C2C=C(O)C(O)=C1O)C=C(O2)C3=CC=CC=C3
Synonyms :
5,6,7-Trihydroxyflavone
MDL No. :MFCD00017459
InChI Key :FXNFHKRTJBSTCS-UHFFFAOYSA-N
Pubchem ID :5281605

Safety of Baicalein

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.70mL

0.74mL

0.37mL

18.50mL

3.70mL

1.85mL

37.00mL

7.40mL

3.70mL

References

[1]Patwardhan RS, Sharma D, et al. Baicalein exhibits anti-inflammatory effects via inhibition of NF-κB transactivation. Biochem Pharmacol. 2016 May 15;108:75-89.

[2]Ma X, Yan W, et al. Baicalein suppresses metastasis of breast cancer cells by inhibiting EMT via downregulation of SATB1 and Wnt/β-catenin pathway. Drug Des Devel Ther. 2016 Apr 18;10:1419-41.

[3]Shieh DE, Liu LT, Lin CC. Antioxidant and free radical scavenging effects of baicalein, baicalin and wogonin. Anticancer Res. 2000 Sep-Oct;20(5A):2861-5

[4]Yu M, Qi B, Xiaoxiang W, Xu J, Liu X. Baicalein increases cisplatin sensitivity of A549 lung adenocarcinoma cells via PI3K/Akt/NF-κB pathway. Biomed Pharmacother. 2017 Jun;90:677-685

[5]Patwardhan RS, Sharma D, Thoh M, Checker R, Sandur SK. Baicalein exhibits anti-inflammatory effects via inhibition of NF-κB transactivation. Biochem Pharmacol. 2016 May 15;108:75-89

[6]Ma X, Yan W, Dai Z, Gao X, Ma Y, Xu Q, Jiang J, Zhang S. Baicalein suppresses metastasis of breast cancer cells by inhibiting EMT via downregulation of SATB1 and Wnt/β-catenin pathway. Drug Des Devel Ther. 2016 Apr 18;10:1419-41

[7]Yan W, Ma X, Zhao X, Zhang S. Baicalein induces apoptosis and autophagy of breast cancer cells via inhibiting PI3K/AKT pathway in vivo and vitro. Drug Des Devel Ther. 2018 Nov 16;12:3961-3972

[8]Yang S, Wang H, Yang Y, Wang R, Wang Y, Wu C, Du G. Baicalein administered in the subacute phase ameliorates ischemia-reperfusion-induced brain injury by reducing neuroinflammation and neuronal damage. Biomed Pharmacother. 2019 Sep;117:109102

 

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