LIQUIRITIGENIN CAS 578-86-9
Introduction：Basic information about LIQUIRITIGENIN CAS 578-86-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
LIQUIRITIGENIN Basic informationDescription References
| Product Name: | LIQUIRITIGENIN |
| Synonyms: | 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;(2S)-Liquiritigenin;(S)-2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;(S)-7-Hydroxy-2-(p-hydroxyphenyl)chroman-4-one;(2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one;4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-, (2S)- |
| CAS: | 578-86-9 |
| MF: | C15H12O4 |
| MW: | 256.25 |
| EINECS: | |
| Product Categories: | Flavanones;sy;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;578-86-9 |
| Mol File: | 578-86-9.mol |
LIQUIRITIGENIN Chemical Properties
| 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. | 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 |
| 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 |
Safety Information
| WGK Germany | 3 |
| HS Code | 29329990 |
| Storage Class | 11 - Combustible Solids |
| 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:
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| 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 Preparation Products And Raw materials
| Raw materials | 7-Hydroxy-2-(p-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-3-one-->4-METHOXYCINNAMIC ACID |
| Preparation Products | β-D-Glucose-->7,4'-DIHYDROXYFLAVONE |
