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Bavachin

Alias: CorylifolinBavachin
Cat No.:V31963 Purity: ≥98%
Bavachin is a natural flavonoid extracted from psoralen seeds.
Bavachin
Bavachin Chemical Structure CAS No.: 19879-32-4
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
Other Sizes
Official Supplier of:
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Product Description
Bavachin is a natural flavonoid extracted from psoralen seeds. It works as a phytoestrogen and activates estrogen receptors ERα and ERβ with EC50s of 320 and 680 nM respectively.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Melanin synthesis and TYR activity are both markedly suppressed by bevacichin. In A375 cells, bevacichin (10 µM) suppresses the expression of TYR and JNK proteins as well as TYR, TRP-1, TRP-2, ERK1, ERK2, and JNK2 mRNA. Following psoralen dihydroflavone treatment, ICI182780 and U0126 cAN substantially reduced the protein expression levels and mRNA expression of TYR, TRP-1, TRP-2, ERK1, ERK2, and JNK2 [1]. In ORO staining tests, bevacicol accumulates lipids in a dose-dependent manner. When compared to control cells, Bavachin at 10 µM dramatically boosted preadipocyte proliferation in the MTT experiment. Moreover, during preadipocyte proliferation, bevacichin can enhance BrdU's binding to freshly produced DNA. Insulin improved BrdU incorporation; this effect was further amplified when insulin and tonic hydroflavone were administered together at 2 µM and 10 µM. In differentiated adipocytes, bevacichin stimulates PPARγ transcriptional activity and activates adipogenic factors. Bavachin increases the absorption of glucose induced by insulin by means of the GLUT4 translocation of the AMPK and Akt pathways [2]. The activities of hMAO-A and hMAO-B are considerably increased by BVN [3]. In recombinant ER, bavacin competitively displaces [3H]E2 to demonstrate ER ligand-binding activity. Using ERα or ERβ and estrogen-responsive luciferase plasmids, the estrogenic activity of Bavachin was assessed in CV-1 cells by a transient transfection technique; the EC50 values were 320 nM and 680 nM, respectively. Bavachin increases the mRNA levels of estrogen-responsive genes (such as pS2 and PR) and decreases the protein level of ERα through the proteasome pathway [4].
References

[1]. Effects of bavachin and its regulation of melanin synthesis in A375 cells. Biomed Rep. 2016 Jul;5(1):87-92. Epub 2016 May 20.

[2]. Bavachin from Psoralea corylifolia Improves Insulin-Dependent Glucose Uptake through Insulin Signaling and AMPK Activation in 3T3-L1 Adipocytes. Int J Mol Sci. 2016 Apr 8;17(4):527.

[3]. Evaluation of the Inhibitory Effects of Bavachinin and Bavachin on Human Monoamine Oxidases A and B. Evid Based Complement Alternat Med. 2015;2015:852194.

[4]. Activation of Estrogen Receptor by Bavachin from Psoralea corylifolia. Biomol Ther (Seoul). 2012 Mar;20(2):183-8.

Additional Infomation
Bavachin has been reported in Lespedeza floribunda, Lespedeza cyrtobotrya, and other organisms with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₂₀H₂₀O₄
Molecular Weight
324.37
Exact Mass
324.136
CAS #
19879-32-4
PubChem CID
14236566
Appearance
White to light yellow solid powder
Density
1.2±0.1 g/cm3
Boiling Point
558.3±50.0 °C at 760 mmHg
Flash Point
202.1±23.6 °C
Vapour Pressure
0.0±1.6 mmHg at 25°C
Index of Refraction
1.622
LogP
4.85
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Heavy Atom Count
24
Complexity
474
Defined Atom Stereocenter Count
1
SMILES
CC(=CCC1=CC2=C(C=C1O)O[C@@H](CC2=O)C3=CC=C(C=C3)O)C
InChi Key
OAUREGNZECGNQS-IBGZPJMESA-N
InChi Code
InChI=1S/C20H20O4/c1-12(2)3-4-14-9-16-18(23)11-19(24-20(16)10-17(14)22)13-5-7-15(21)8-6-13/h3,5-10,19,21-22H,4,11H2,1-2H3/t19-/m0/s1
Chemical Name
(2S)-2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
Synonyms
CorylifolinBavachin
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~308.29 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.41 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (6.41 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (6.41 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0829 mL 15.4145 mL 30.8290 mL
5 mM 0.6166 mL 3.0829 mL 6.1658 mL
10 mM 0.3083 mL 1.5414 mL 3.0829 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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