Liquiritigenin

Alias: MenerbaLiquiritigenin MF101 MF 101 MF-101
Cat No.:V10076 Purity: ≥98%
Liquiritigenin is a flavanone extracted from licorice.
Liquiritigenin Chemical Structure CAS No.: 578-86-9
Product category: Estrogenprogestogen Receptor
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Liquiritigenin:

  • (±)-Liquiritigenin ((±)-4',7-Dihydroxyflavanone)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Liquiritigenin is a flavanone extracted from licorice. It is a selective estrogen receptor beta (ERβ) agonist with EC50 of 36.5 nM for activating ERE tk-Luc.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Liquiritigenin transfects U2OS cells with ERβ but not ERα, and this results in dose-responsive activation of ERE tk-Luc. Liquiritigenin caused temporal excitation of CECR6, NKG2E, and NKD in addition to dosage activation of ERβ but not ERα. Liquiritigenin's ERβ selectivity results from the coactivator shock coactivator-like 2 being selectively recruited to target genes. Liquiritigenin binds to ERα and ERβ with comparable affinities, which leads to the selective recruitment of SRC-2 to target genes in ERβ cells [Liquiritigenin MC3T3-E1 cells inhibits the production of TNF-α, intracellular reactive oxygen species, protein adducts, MG-induced osteoblast MC3T3-E1 death, mitochondrial superoxide, and cardiolipin peroxidation [1]. 2].
ln Vivo
In a mouse xenograft model, liquiditrigenin did not increase the size of the epidermis or cause carcinogenesis in MCF-7 breast cancer cells [1]. Treatment with lichidetinin has the ability to markedly lower serum and hippocampal concentrations of pro-inflammatory cytokines, including as interleukin (IL)-6, IL-1β, and tumor necrosis factor (TNF)-α [3].
References
[1]. Mersereau JE, et al. Liquiritigenin is a plant-derived highly selective estrogen receptor beta agonist. Mol Cell Endocrinol. 2008 Feb 13;283(1-2):49-57.
[2]. Suh KS, et al. Protective effect of liquiritigenin against methylglyoxal cytotoxicity in osteoblastic MC3T3-E1 cells. Food Funct. 2014 Jul 25;5(7):1432-40.
[3]. Tao W, et al. Liquiritigenin reverses depression-like behavior in unpredictable chronic mild stress-induced mice by regulating PI3K/Akt/mTOR mediated BDNF/TrkB pathway. Behav Brain Res. 2016 Jul 15;308:177-86
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H12O4
Molecular Weight
256.25
Exact Mass
256.0736
CAS #
578-86-9
Related CAS #
(±)-Liquiritigenin;69097-97-8
SMILES
O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=CC(O)=CC=C13
InChi Key
FURUXTVZLHCCNA-AWEZNQCLSA-N
InChi Code
InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1
Chemical Name
(S)-7-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
Synonyms
MenerbaLiquiritigenin MF101 MF 101 MF-101
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 : ~125 mg/mL (~487.80 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.42 mg/mL (9.44 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 24.2 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: ≥ 2.42 mg/mL (9.44 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 24.2 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: ≥ 2.42 mg/mL (9.44 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 24.2 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 3.9024 mL 19.5122 mL 39.0244 mL
5 mM 0.7805 mL 3.9024 mL 7.8049 mL
10 mM 0.3902 mL 1.9512 mL 3.9024 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.

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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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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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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.

Biological Data
  • Liquiritigenin selectively activates transcription through ERβ.
  • The activation by liquiritigenin is selective for the estrogen receptor. U2OS were transfected with TAT3-luciferase and androgen receptor (AR) (A), MMTV-luciferase and glucocorticoid receptor (GR) (B), TAT3-luciferase and progesterone receptor B (PR) (C), or F2 tk-Luc and thyroid hormone receptor β1 (TR) (D). The cells were treated for 18 h with 1 nM dihydrotestosterone (DHT), or 1 nM dexamethasone (Dex), or 1 nM progesterone (Prog), or 10 nM triiodothyronine (T3) (A, B, C, D, respectively) or 2.5 μM liquiritigenin (Liq). Each data point is the average of triplicate determinations ± S.E.M. An activation by the drug was significant (p < 0.05) when it was 2-fold greater than the control values.
  • Liquiritigenin selectively activates transcription of the native ER regulatory elements and genes through ERβ. CECR6 tk-Luc (A), NKG2E tk-Luc (B), and NKD tk-Luc (C) were cotransfected into U2OS cells with expression vectors for human ERα or ERβ. After transfection, the cells were treated for 18 h with increasing amounts of liquiritigenin and luciferase activity was measured. U2OS cells stably transfected with tetracycline inducible ERβ or ERα were treated with 1 μg/ml doxycycline for 18 h to induce ER expression. The cells were then treated for increasing times with liquiritigenin. The level of CECR6 (D), NKG2E (E), and NKD (F) mRNA was measured by real-time PCR. Each data point is the average of triplicate determinations ± S.E.M. An activation by the drug was significant (p < 0.05) when it was 2-fold greater than the control values.
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