578-86-9

Basic information

• Product Name: LIQUIRITIGENIN
• Synonyms: 4',7-DIHYDROXYFLAVANONE;7,4'-DIHYDROXYFLAVANONE;LIQUIRITIGENIN;LIQUIRITIGENIN(P);LIQUIRITIGENIN WITH HPLC;7,4''-DIHYDROXYFLAVANONE hplc;(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
• CAS NO: 578-86-9
• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.25
• Product Categories: Flavanones;sy;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 578-86-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 206-208°C
• Boiling Point: 529.5 °C at 760 mmHg
• Flash Point: 207℃
• Appearance: /
• Density: 1.386 g/cm³
• Vapor Pressure: 7.94E-12mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.71±0.40(Predicted)
• BRN: 359378
• CAS DataBase Reference: LIQUIRITIGENIN(CAS DataBase Reference)
• NIST Chemistry Reference: LIQUIRITIGENIN(578-86-9)
• EPA Substance Registry System: LIQUIRITIGENIN(578-86-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 578-86-9(Hazardous Substances Data)

Usage

Description

Liquiritigenin is a flavonoid and an estrogenic compound found in licorice (Glycyrrhizae radix) root extract and several other plants. It is an active estrogenic component in extracts of Glycyrrhizae radix, which is frequently used for life-enhancing properties, treatment of injury or swelling, detoxification in traditional Oriental medicine, and as a food supplement in many countries. Liquiritigenin is a selective estrogen receptor-β (ERβ) agonist, activating 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. It is associated with anti-inflammatory effects and is also reported to have antihyperlipidemic, antiallergic, and antihepatocellular carcinoma effects.

Uses

Used in Pharmaceutical Industry:
Liquiritigenin is used as a reference standard for ultra-performance liquid chromatography (UPLC) of Chaihu-Shugan-San (CSS) extract, which is a traditional Chinese medicine formula.
Used in Anticancer Applications:
Liquiritigenin is used as an agent to study its inhibitory effect on tumor metastasis in the treatment of colorectal cancer.
Used in Antiviral Applications:
Liquiritigenin is used as a potential antiviral drug against hepatitis C virus (HCV) infection.

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

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.]

InChI:InChI=1/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

Upstream product

• 551-15-5 liquiritin 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 151-10-0 1,3-Dimethoxybenzene 
• 961-29-5 isoliquirtigenin 
• 69097-97-8 7,4'-dihydroxy-dihydroflavone 
• 60-18-4 L-tyrosine 

Downstream Products

• 2196-14-7 7,4'-Dihydroxyflavon 
• 486-66-8 daidzein 
• 961-29-5 isoliquirtigenin 
• 54301-00-7 liquiritigenin-7,4'-diacetate 
• 2034-65-3 resokaempferol 
• 528-48-3 3,7,3',4'-tetrahydroxyflavone 
• 31524-62-6 ((2S)-2,3-dihydro-7-hydroxy-2-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one 
• 7400-08-0 para-coumaric acid 
• 108-46-3 recorcinol 
• 131887-80-4 (2R,3S)-2,7,4'-trihydroxyisoflavanone 
• 92549-54-7 (2S)-7,4'-dihydroxyflavan-4-ol 

Relevant articles and documents

Liquiritigenin inhibits hepatic fibrogenesis and TGF-β1/Smad with Hippo/YAP signal

Background: Recent reports highlighted the possibility that Yes-associated protein (YAP) and transforming growth factor-β1 (TGF-β1) can act as critical regulators of hepatic stellate cells (HSCs) activation; therefore, it is natural for compounds targeting Hippo/YAP and TGF-β1/Smad signaling pathways to be identified as potential anti-fibrotic candidates. Purpose: Liquiritigenin (LQ) is an aglycone of liquiritin and has been reported to protect the liver from injury. However, its effects on the Hippo/YAP and TGF-β1/Smad pathways have not been identified to date. Methods: We conducted a series of experiments using CCl4-induced fibrotic mice and cultured LX-2 cells. Result: LQ significantly inhibited liver fibrosis, as indicated by decreases in regions of hepatic degeneration, inflammatory cell infiltration, and the intensity of α-smooth muscle actin (α-SMA) staining in mice. Moreover, LQ blocked the TGF-β1-induced phosphorylation of Smad 3, and the transcript levels of plasminogen activator inhibitor-1 (PAI-1) and matrix metalloproteinase-2 (MMP-2) in LX-2 cells, which is similar with resveratrol and oxyresveratrol (positive controls). Furthermore, LQ increased activation of large tumor suppressor kinase 1 (LATS1) with the induction of YAP phosphorylation, thereby preventing YAP transcriptional activity and suppressing the expression of exacerbated TGF-β1/Smad signaling molecules. Conclusion: These results clearly show that LQ ameliorated experimental liver fibrosis by acting on the TGF-β1/Smad and Hippo/YAP pathways, indicating that LQ has the potential for effective treatment of liver fibrosis.

METHOD FOR PRODUCING LIQUIRITIGENIN PRECURSOR

An objective of this invention is to provide a mass manufacturing method for providing liquiritigenin by a proper method. The present invention provides a method for producing isoliquiritigenin by bringing a 4-alkoxy cinnamic acid represented by formula (I) and a 1,3-alkoxybenzene represented by formula (II) into Friedel-Crafts reaction (A) for coupling to a trialkoxy isoliquiritigenin represented by a synthesis formula (III) and allowing it to be crystal, and removing protection group to obtain an isoliquiritigenin represented by formula (IV), wherein, an in situ liquiritigenin (-) pharmacological effect is obtained by administrating the isoliquiritigenin represented by formula (IV)as a precursor of liquiritigenin into body.

Highly efficient and green synthesis of flavanones and tetrahydroquinolones

Highly efficient and green catalytic conversion of 2′-hydroxy and 2′-amino chalcones to flavanones and tetrahydroquinolones is reported herein. 2′-Hydroxy and 2′-amino chalcones can be almost completely converted to flavanones and tetrahydroquinolones in just 2 min in the presence of piperidine and KOH under room temperature. Liquiritigenin is also efficiently synthesized under similar conditions.