Liquiritigenin - 10mM in DMSO , CAS No.578-86-9

CAS: 578-86-9 Cat. No.: L424865 Formula: C₁₅H₁₂O₄ Peso molecolare: 256.25 Beilstein Registry Number: 359378 PubChem CID: 114829

GRADE & PURITY 10mM in DMSO

Synonyms

(S)-liquiritigenin | CCG-267019 | (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one | 4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-,(2S)- | DB03601 | FURUXTVZLHCCNA-AWEZNQCLSA-N | T-BUTOXYBIS(DIMETHYLAMINO)METHANE | Q6557526

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Panoramica

Liquiritigenin is a flavonoid and an estrogenic compound found in licorice (Glycyrrhizae radix) root extract and several other plants.

Application：
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.

Specifications

Sinonimi

(S)-liquiritigenin | CCG-267019 | (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one | 4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-,(2S)- | DB03601 | FURUXTVZLHCCNA-AWEZNQCLSA-N | T-BUTOXYBIS(DIMETHYLAMINO)METHANE | Q6557526

Specifiche e purezza

10mM in DMSO

Meccanismi biochimici e fisiologici

Liquiritigenin is a flavanone found in Radix glycyrrhizae and shown to induce apoptosis in SMM-721 cells by disruption of the mitochondrial membrane potential and increased production of reactive oxygen species

Condizioni di conservazione di stoccaggio

Store at -80°C

Spedito in

Dry ice packs + Cold packs

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Nomi e identificatori

• Pubchem Sid: 528773375
• Sorrisi canonici: Oc1ccc(cc1)[C@@H]2CC(=O)c3ccc(O)cc3O2
• IUPAC Name: (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• InChIKey: FURUXTVZLHCCNA-AWEZNQCLSA-N
• 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
• Isomeri SMILES: C1[C@H](OC2=C(C1=O)C=CC(=C2)O)C3=CC=C(C=C3)O
• WGK Germania: 3
• RTECS: DJ2981789
• PubChem CID: 114829
• Peso molecolare: 256.25
• Beilstein: 359378

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Flavonoids
      • Subclass Flavans

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Flavonoids
• Subclass: Flavans
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavanones
• Alternative Parents: 7-hydroxyflavonoids 4'-hydroxyflavonoids Chromones Aryl alkyl ketones Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 4'-hydroxyflavonoid - 7-hydroxyflavonoid - Hydroxyflavonoid - Flavanone - Chromone - Chromane - 1-benzopyran - Benzopyran - Aryl alkyl ketone - Aryl ketone - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Monocyclic benzene moiety - Benzenoid - Ketone - Oxacycle - Organoheterocyclic compound - Ether - Organic oxygen compound - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as flavanones. These are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
• External Descriptors: Flavanones

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Obiettivi associati (umani)

CYP19A1 Tclin Aromatase (1 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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CYP19A1 Tclin Cytochrome P450 19A1 (6099 Activities)

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TYR Tclin Tyrosinase (717 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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XDH Tclin Xanthine dehydrogenase (1038 Activities)

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ESR2 Tclin Estrogen receptor beta (9272 Activities)

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JUN Tchem Proto-oncogene c-JUN (434 Activities)

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CYP1B1 Tchem Cytochrome P450 1B1 (1148 Activities)

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MMP3 Tchem Matrix metalloproteinase 3 (3433 Activities)

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CYP1A1 Tchem Cytochrome P450 1A1 (1169 Activities)

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MMP7 Tchem Matrix metalloproteinase 7 (1073 Activities)

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MMP1 Tchem Matrix metalloproteinase-1 (7046 Activities)

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YES1 Tclin Tyrosine-protein kinase YES (2781 Activities)

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CCRF-CEM (65223 Activities)

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DU-145 (51482 Activities)

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HCT-8 (3484 Activities)

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HL-60 (67320 Activities)

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HT-1080 (3966 Activities)

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K562 (73714 Activities)

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MCF7 (126967 Activities)

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PANC-1 (6144 Activities)

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SGC-7901 (2773 Activities)

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SW480 (6023 Activities)

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U-937 (7138 Activities)

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A549 (127892 Activities)

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T47D (39041 Activities)

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HCT-116 (91556 Activities)

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HepG2 (196354 Activities)

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Ishikawa (877 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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RELA Tchem Nuclear factor NF-kappa-B p65 subunit (627 Activities)

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PSMB5 Tclin Proteasome Macropain subunit MB1 (2451 Activities)

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NA Neuraminidase (1107 Activities)

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Mmp13 Matrix metalloproteinase 13 (19 Activities)

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Mmp2 Matrix metalloproteinase-2 (12 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Influenza A virus (11224 Activities)

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B16 (5829 Activities)

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MDCK (10148 Activities)

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RAW264.7 (28094 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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BCHE Cholinesterase (8742 Activities)

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Prevotella intermedia (369 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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prtC Collagenase (8 Activities)

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SARS-CoV-2 (38078 Activities)

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Meccanismi d'azione

Proprietà chimiche e fisiche

• Peso molecolare: 256.250 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 256.074 Da
• Monoisotopic Mass: 256.074 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 335.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Riferimenti

1. Xiaoran Ning, Yanhui Ni, Jingjing Cao, Huaxing Zhang.  (2023)  Liquiritigenin Attenuated Collagen-Induced Arthritis and Cardiac Complication via Inflammation and Fibrosis Inhibition in Mice.  CHEMICAL & PHARMACEUTICAL BULLETIN,  71  (4): (269-276).  [PMID:37005251] [10.1248/cpb.c22-00684]

2. Bin Guo, Xu-Ran Fan, Zhong-Ze Fang, Yun-Feng Cao, Cui-Min Hu, Julin Yang, Yan-Yan Zhang, Rong-Rong He, Xu Zhu, Zhen-Wen Yu, Xiao-Yu Sun, Mo Hong, Lu Yang.  (2012)  Deglycosylation of Liquiritin Strongly Enhances its Inhibitory Potential Towards UDP-Glucuronosyltransferase (UGT) Isoforms.  PHYTOTHERAPY RESEARCH,  27  (8): (1232-1236).  [PMID:23065713] [10.1002/ptr.4855]

3. Yinhuang Gao, Peng Zhao, Chunyan Wang, Keren Fang, Yueqing Pan, Yan Zhang, Zhishuo Miao, Meirong Wang, Minlong Wei, Wei Zou, Menghua Liu, Kang Peng.  (2024)  Buqi Huoxue Tongnao prescription protects against chronic cerebral hypoperfusion via regulating PI3K/AKT and LXRα/CYP7A1 signaling pathways.  PHYTOMEDICINE,      [PMID:38959552] [10.1016/j.phymed.2024.155844]

4. Ziyao Chen, Dongju Zhao, Meng Cheng, Fan Yang, Yining Liu, Jin Chang, Yan Dou.  (2024)  Female-sensitive multifunctional phytoestrogen nanotherapeutics for tailored management of postmenopausal Alzheimer's disease.  Nano Today,      [PMID:] [10.1016/j.nantod.2023.102119]

5. Peng Deng, Qifan Wang, Shengfang Wu, Xiuwen Zhou, Fatih Oz, Qiuming Chen, Zhaojun Wang, Zhiyong He, Jie Chen, Maomao Zeng.  (2025)  Synergistic effect of spice extracts on multiple hazards formation and sensory markers in beef flavoring.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2025.106099]

6. Na Li, Liyan Liu, Huiqing Luo, Huaqiao Wang, Depo Yang, Feng He.  (2020)  Flavanone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics for Mitochondria-Imaging and Zebrafish-Imaging.  MOLECULES,  25  (14): (3298).  [PMID:32708080] [10.3390/molecules25143298]

7. Hui Cao, Xiaojuan Liu, Nataša Poklar Ulrih, Pradeep K. Sengupta, Jianbo Xiao.  (2018)  Plasma protein binding of dietary polyphenols to human serum albumin: A high performance affinity chromatography approach.  FOOD CHEMISTRY,      [PMID:30174044] [10.1016/j.foodchem.2018.07.111]

8. Fangfei Zhou, Qingge Lu, Lingyu Kong, Sitong Wang, Haixia Zhang, Meng Zhao, Yue Hu, Fanwu Wu, Chenxi Wu.  (2025)  Glycyrrhiza uralensis Fisch. suppresses cell migration via ROS and JAK/STAT signalling pathways in Drosophila.  Frontiers in Pharmacology,      [PMID:40657637] [10.3389/fphar.2025.1549920]

9. Ruoxue Bai, Manling Li, Yingyi Zhang, Jiangwei He, Yujin Lin, Haoran Zhang, Ping Shu, Xiaojing Yan, Bo wang, Tingting Huang, Xue Zhao, Xinfeng Zhao.  (2025)  Purification-free immobilization of dopamine D2 receptor and glucocorticoid receptor by alkyne–azide cycloaddition for affinity chromatography-based drug screening.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:41352078] [10.1016/j.chroma.2025.466596]

10. Ying Liu, Linlin Yu, Le Wang, Xiaowei Fang, Tenggao Zhu, Huanwen Chen, Wenliu Zhang, Dong Wu.  (2026)  Changes in Components During Quality Formation and Evaluation of Honey-Processed Glycyrrhiza uralensis Fisch. from Different Geographical Origins by Sequential Electrospray Ionization Mass Spectrometry.  ACS Omega,      [PMID:41585634] [10.1021/acsomega.5c08675]

11. Xiang Meng, Muzhou Xue, Zequn Zeng, Wenbin Pei, Bing Gong.  (2026)  Liquiritigenin-loaded poly (acrylic acid)-carboxymethyl cellulose hydrogels: formulation optimization, performance evaluation, and assessment of therapeutic efficacy for wound healing and sepsis caused by wound bacterial infection.  Frontiers in Bioengineering and Biotechnology,      [PMID:41625074] [10.3389/fbioe.2025.1732535]

12. Qin Zhou, Yushi Wei, Yijing Liao, Deming Gong, Guowen Zhang.  (2026)  Inhibition effect of vitamin B6 on α-glucosidase and mechanism of its synergistic inhibition with liquiritigenin.  FOOD CHEMISTRY,      [PMID:41592502] [10.1016/j.foodchem.2026.148130]

13. Jingwen Li, Hossain M. Zabed, Yufei Zhang, Junhua Yun, Yuehui Tian, Guoyan Zhang, Xianghui Qi.  (2026)  Rational metabolic reprogramming of yeast across multiple pathway nodes for de novo liquiritigenin biosynthesis from glucose.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2026.109513]