| Identification | Back Directory | [Name]
LIQUIRITIGENIN | [CAS]
578-86-9 | [Synonyms]
Aids095895
Aids-095895
liquirtigenin
LIQUIRITIGENIN
LIQUIRITIGENIN(P)
(2S)-Liquiritigenin
Liquiritigenin, >=98%
4',7-DIHYDROXYFLAVANONE
7,4'-DIHYDROXYFLAVANONE
LIQUIRITIGENIN WITH HPLC
7,4''-DIHYDROXYFLAVANONE hplc
(?)-Liquiritigenin Radix glycyrrhizae
Liquiritigenin (=7,4'-Dihydroxyflavanone)
(S)-7-Hydroxy-2-(p-hydroxyphenyl)chroman-4-one
(S)-7-Hydroxy-2-(4-hydroxyphenyl)chroMan-4-one
(S)-2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
(2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
(2S)-2α-(4-Hydroxyphenyl)-7-hydroxy-2,3-dihydro-4H-1-benzopyran-4-one
(2S)-2α-(4-Hydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-, (2S)- | [Molecular Formula]
C15H12O4 | [MDL Number]
MFCD00287289 | [MOL File]
578-86-9.mol | [Molecular Weight]
256.25 |
| Chemical Properties | Back Directory | [Melting point ]
206-208°C | [Boiling point ]
529.5±50.0 °C(Predicted) | [density ]
1.386±0.06 g/cm3(Predicted) | [Fp ]
207℃ | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
DMSO : 125 mg/mL (487.80 mM; Need ultrasonic) | [form ]
powder | [pka]
7.71±0.40(Predicted) | [color ]
White | [BRN ]
359378 | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [Cosmetics Ingredients Functions]
ANTIOXIDANT
SKIN CONDITIONING | [InChI]
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 | [InChIKey]
FURUXTVZLHCCNA-AWEZNQCLSA-N | [SMILES]
[C@H]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC=C2C(=O)C1 |
| Hazard Information | Back Directory | [Definition]
ChEBI: A dihydroxyflavanone compound having the two hydroxy substituents at the 4'- and 7-positions. Isolated from the root of Glycyrrhizae uralensis, it is a selective agonist for oestrogen receptor beta. | [Uses]
Liquiritigenin has been used:
- to study its inhibitory effect on tumor metastasis in the treatment of colorectal cancer
- as a reference standard for ultra-performance liquid chromatography (UPLC) of Chaihu-Shugan-San (CSS) extract
- as a potential antiviral drug against hepatitis C virus (HCV) infection
| [General Description]
Liquiritigenin is a flavonoid and an estrogenic compound found in licorice (Glycyrrhizae radix) root extract and several other plants. | [Biochem/physiol Actions]
Liquiritigenin displays anti-diabetic and choleretic properties. It exerts anti-inflammatory activity on Raw246.7 cells by inhibiting nuclear factor kappa light chain enhancer of activated B cells (NF-κB)-dependent-induction of inducible NOS (iNOS). Liquiritigenin inhibits liver fibrogenesis by blocking Hippo/Yes-associated protein (YAP) and transforming growth factor-β1 (TGF-β1)/small mothers against decapentaplegic (Smad) components. It is a selective estrogen receptor β agonist cells. Liquiritigenin induces apoptosis in SMM-721 cells by disruption of the mitochondrial membrane potential and increased production of reactive oxygen species. | [Purification Methods]
It crystallises from aqueous 50% EtOH. [Beilstein 18 III/IV 1780, 18/4 V 82.] |
| Questions And Answer | Back Directory | [Description]
Liquiritigenin is an active estrogenic component in extracts of Glycyrrhizae radix. Glycyrrhizae radix (G. radix, licorice, liquorice) is frequently used for life-enhancing properties, for the treatment of injury or swelling, for detoxification in traditional Oriental medicine, as well as a food supplement in many of the countries in the world. Liquiritigenin is a selective estrogen receptor-β (ERβ) agonist. Liquiritigenin activates multiple ER regulatory elements and native target genes with ERβ but not ERα. The ERβ-selectivity of liquiritigenin is due to the selective recruitment of the coactivator steroid receptor coactivator-2 to target genes.
As the targeting ERβ is associated with anti-inflammatory effects, liquiritigenin exerts anti-inflammatory effects. Liquiritigenin is also reported to antihyperlipidemic, antiallergic and antihepatocellular carcinoma effects.
| [References]
[1] J. E. Mersereau, N. Levy, R. E. Staub, S. Baggett, T. Zogric, S. Chow, W. A. Ricke, M. Tagliaferri, I. Cohen, L. F. Bjeldanes (2008) Liquiritigenin is a plant-derived highly selective estrogen receptor β agonist, Molecular and Cellular Endocrinology, 283, 49-57
[2] Di Wang, Jiahui Lu, Yan Liu, Qingfan Meng, Jing Xie, Zhenzuo Wang,Lesheng Teng (2014) Liquiritigenin Induces Tumor Cell Death through Mitogen-Activated Protein Kinase- (MPAKs-) Mediated Pathway in Hepatocellular Carcinoma Cells, BioMed Research International, 2014, Article ID 965316
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