LIQUIRITIGENIN Chemical Properties

Melting point:

206-208°C

Boiling point:

529.5±50.0 °C(Predicted)

Density 

1.386±0.06 g/cm3(Predicted)

Flash point:

207℃

storage temp. 

under inert gas (nitrogen or Argon) at 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

InChIKey

FURUXTVZLHCCNA-AWEZNQCLSA-N

Safety Information

WGK Germany 

3

HS Code 

29329990

LIQUIRITIGENIN Usage And Synthesis

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

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

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.

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.]

LIQUIRITIGENIN(578-86-9)Related Product Information

• Ascorbic Acid
• Liguiritigenin-7-O-D-apiosyl-4’-O-D-glucoside
• LICOCHALCONE-A
• LIQUIRITIGENIN
• LIQUIRITIN(SH)
• ISOLIQUIRITIN
• isoliquiritin apioside
• Isoliquiritigenin
• Loratadine
• LICOCHALCONEC
• Licochalcone B
• Glepidotin A
• GLABRENE
• Glepidotin B
• 7-O-METHYL-LIQUIRITIGENIN
• 4'-Glucosyl-iso-liquiritigenin
• Glepidotin C
• 4'-Diglucosyl-iso-liquiritigenin