Liquiritigenin
Liquiritigenin structure
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Common Name | Liquiritigenin | ||
|---|---|---|---|---|
| CAS Number | 578-86-9 | Molecular Weight | 256.253 | |
| Density | 1.4±0.1 g/cm3 | Boiling Point | 529.5±50.0 °C at 760 mmHg | |
| Molecular Formula | C15H12O4 | Melting Point | 206-208ºC | |
| MSDS | N/A | Flash Point | 206.9±23.6 °C | |
Use of LiquiritigeninLiquiritigenin, a flavanone isolated from Glycyrrhiza uralensis, is a highly selective estrogen receptor β (ERβ) agonist with an EC50 of 36.5 nM for activation of the ERE tk-Luc. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | liquiritigenin |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | Liquiritigenin, a flavanone isolated from Glycyrrhiza uralensis, is a highly selective estrogen receptor β (ERβ) agonist with an EC50 of 36.5 nM for activation of the ERE tk-Luc. |
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| Related Catalog | |
| Target |
EC50: 36.5 nM (activation of the ERE tk-Luc)[1] |
| In Vitro | Liquiritigenin produces a dose-response activation of ERE tk-Luc in the U2OS cells transfected with ERβ, but not ERα. Liquiritigenin produces a dose-dependent activation and a time-dependent increase of the CECR6, NKG2E and NKD with ERβ but not with ERα. The ERβ-selectivity of liquiritigenin is due to the selective recruitment of the coactivator steroid receptor coactivator-2 to target genes. Liquiritigenin exhibits similar binding affinities for ERα and ERβ, and causes the recruitment of SRC-2 to target genes selectively in ERβ cells[1]. Pretreatment of MC3T3-E1 cells with liquiritigenin prevents the MG-induced cell death and production of protein adduct, intracellular reactive oxygen species, mitochondrial superoxide, cardiolipin peroxidation, and TNF-α in osteoblastic MC3T3-E1 cells[2]. |
| In Vivo | In a mouse xenograph model, liquiritigenin does not stimulate uterine size or tumorigenesis of MCF-7 breast cancer cells[1]. Treatment with liquiritigenin significantly reduces the concentrations of pro-inflammatory cytokines including interleukin (IL)-6, IL-1β and tumor necrosis factor (TNF)-α in serum and hippocampus[3]. |
| Kinase Assay | The relative binding affinity of liquiritigenin to pure full-length ERα and ERβ is determined using ERα and ERβ competitor assay kits. Fluorescence polarization of the fluorophore-tagged estrogen bound to ERα and ERβ in the presence of increasing amounts of competitor ligand or extract is determined using the GENios Pro microplate reader with fluorescein excitation (485 nM) and emission (530 nM) filters[1]. |
| Animal Admin | Mice: MCF-7 (250,000) cells are grafted under the kidney capsule of nude mice. Five mice per group are treated with a continuous infusion using osmotic pumps containing vehicle, E2 (0.4 mg) or liquiritigenin (2 mg) that infused 2.5 μL/h for 1 month. After one month of treatment, the tumors and uteri are removed and analyzed[1]. |
| References |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Boiling Point | 529.5±50.0 °C at 760 mmHg |
| Melting Point | 206-208ºC |
| Molecular Formula | C15H12O4 |
| Molecular Weight | 256.253 |
| Flash Point | 206.9±23.6 °C |
| Exact Mass | 256.073547 |
| PSA | 66.76000 |
| LogP | 2.76 |
| Vapour Pressure | 0.0±1.4 mmHg at 25°C |
| Index of Refraction | 1.662 |
| InChIKey | FURUXTVZLHCCNA-AWEZNQCLSA-N |
| SMILES | O=C1CC(c2ccc(O)cc2)Oc2cc(O)ccc21 |
This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| Hazard Codes | Xi |
|---|---|
| HS Code | 29329990 |
This table lists upstream starting materials and downstream derivative products related to this chemical.
| Precursor 2 | |
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| DownStream 5 | |
CAS#:961-29-5
CAS#:551-15-5
CAS#:31524-62-6
CAS#:7400-08-0
CAS#:108-46-3
CAS#:2196-14-7
CAS#:486-66-8This table contains target information, in‑vitro & in‑vivo assay data for this compound.
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one |
| (2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one |
| Liquiritigenin |
| (2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What is the LogP of liquiritigenin? |
| A: LogP of liquiritigenin is 2.76. |
| Q: What are the downstream products of liquiritigenin? |
| A: Related downstream products(CAS) of liquiritigenin: 31524-62-6;7400-08-0;108-46-3;2196-14-7;486-66-8. |
| Q: What is the CAS number of liquiritigenin? |
| A: CAS number of liquiritigenin is 578-86-9. |
| Q: What is the boiling point of liquiritigenin? |
| A: Boiling point of liquiritigenin is 529.5±50.0 °C at 760 mmHg. |
| Q: What is the molecular weight of liquiritigenin? |
| A: Molecular weight of liquiritigenin is 256.253. |
| Q: What is the molecular formula of liquiritigenin? |
| A: Molecular formula of liquiritigenin is C15H12O4. |
| Q: What English synonyms does liquiritigenin have? |
| A: English synonyms of liquiritigenin: (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one, (2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one, Liquiritigenin, (2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one. |
| Q: What is the melting point of liquiritigenin? |
| A: Melting point of liquiritigenin is 206-208ºC. |
| Q: What is the polar surface area (PSA) of liquiritigenin? |
| A: Polar surface area (PSA) of liquiritigenin is 66.76000. |
| Q: What are the upstream materials of liquiritigenin? |
| A: Related upstream materials(CAS) of liquiritigenin: 961-29-5;551-15-5. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| BioBioPha |
| Dayang Chem (Hangzhou) Co., Ltd. |
| naturewill |
| Henan Tianfu Chemical Co., Ltd. |