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58749-22-7,MFCD01417903
Catalog No.:AA00IADA

58749-22-7 | Licochalcone A

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5mg
≥95%
in stock  
$70.00   $49.00
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10mg
≥95%
in stock  
$133.00   $93.00
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25mg
≥95%
in stock  
$210.00   $147.00
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50mg
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$386.00   $270.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00IADA
Chemical Name:
Licochalcone A
CAS Number:
58749-22-7
Molecular Formula:
C21H22O4
Molecular Weight:
338.3970
MDL Number:
MFCD01417903
SMILES:
C=CC(c1cc(/C=C/C(=O)c2ccc(cc2)O)c(cc1O)OC)(C)C
Properties
Properties
 
BP:
532.6°C at 760 mmHg  
Form:
Solid  
MP:
100℃  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
488  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
6  
XLogP3:
4.9  

Downstream Synthesis Route
87080-27-1    4426-72-6   
5-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide 

[1]Patent:CN106674115,2017,A.Locationinpatent:Paragraph0014;0015

87080-27-1    537-47-3   
5-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-3-(4-hydroxyphenyl)-N-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide 

[1]Patent:CN106674115,2017,A.Locationinpatent:Paragraph0016;0017

51707-42-7    87080-27-1   
N-(3-chlorophenyl)-5-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide 

[1]Patent:CN106674115,2017,A.Locationinpatent:Paragraph0018;0019

69194-89-4    87080-27-1   
N-(4-chlorophenyl)-5-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide 

[1]Patent:CN106674115,2017,A.Locationinpatent:Paragraph0020;0021

87080-27-1    2231-57-4   
5-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-thiohydrazide 

[1]Patent:CN106674115,2017,A.Locationinpatent:Paragraph0022;0023

Literature

Title: Licochalcone A from licorice root, an inhibitor of human hepatoma cell growth via induction of cell apoptosis and cell cycle arrest.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20181001

Title: Assessment of the inhibition potential of Licochalcone A against human UDP-glucuronosyltransferases.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20160401

Title: Induction of NAD(P)H:Quinone Oxidoreductase 1 (NQO1) by Glycyrrhiza Species Used for Women's Health: Differential Effects of the Michael Acceptors Isoliquiritigenin and Licochalcone A.

Journal: Chemical research in toxicology 20151116

Title: Inhibition of human cytochrome P450 enzymes by licochalcone A, a naturally occurring constituent of licorice.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20151001

Title: Differential Effects of Glycyrrhiza Species on Genotoxic Estrogen Metabolism: Licochalcone A Downregulates P450 1B1, whereas Isoliquiritigenin Stimulates It.

Journal: Chemical research in toxicology 20150817

Title: Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species.

Journal: Microbiology and immunology 20140301

Title: Cranberry proanthocyanidins act in synergy with licochalcone A to reduce Porphyromonas gingivalis growth and virulence properties, and to suppress cytokine secretion by macrophages.

Journal: Journal of applied microbiology 20120801

Title: Licochalcone A prevents adipocyte differentiation and lipogenesis via suppression of peroxisome proliferator-activated receptor γ and sterol regulatory element-binding protein pathways.

Journal: Journal of agricultural and food chemistry 20120523

Title: Guanylate cyclase activator YC-1 potentiates apoptotic effect of licochalcone A on human epithelial ovarian carcinoma cells via activation of death receptor and mitochondrial pathways.

Journal: European journal of pharmacology 20120515

Title: Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans.

Journal: Mycoses 20111101

Title: Design, synthesis, and evaluation of bromo-retrochalcone derivatives as protein tyrosine phosphatase 1B inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20110615

Title: Comparative trial of moisturizer containing licochalcone A vs. hydrocortisone lotion in the treatment of childhood atopic dermatitis: a pilot study.

Journal: Journal of the European Academy of Dermatology and Venereology : JEADV 20110601

Title: Chalcones as novel influenza A (H1N1) neuraminidase inhibitors from Glycyrrhiza inflata.

Journal: Bioorganic & medicinal chemistry letters 20110101

Title: Reinvestigation of structure-activity relationship of methoxylated chalcones as antimalarials: synthesis and evaluation of 2,4,5-trimethoxy substituted patterns as lead candidates derived from abundantly available natural β-asarone.

Journal: European journal of medicinal chemistry 20101101

Title: Licochalcones suppress degranulation by decreasing the intracellular Ca2+ level and tyrosine phosphorylation of ERK in RBL-2H3 cells.

Journal: International immunopharmacology 20100701

Title: Influence of subinhibitory concentrations of licochalcone A on the secretion of enterotoxins A and B by Staphylococcus aureus.

Journal: FEMS microbiology letters 20100601

Title: Subinhibitory concentrations of licochalcone A decrease alpha-toxin production in both methicillin-sensitive and methicillin-resistant Staphylococcus aureus isolates.

Journal: Letters in applied microbiology 20100201

Title: Licochalcone A potently inhibits tumor necrosis factor alpha-induced nuclear factor-kappaB activation through the direct inhibition of IkappaB kinase complex activation.

Journal: Molecular pharmacology 20091001

Title: Licorice and licochalcone-A induce autophagy in LNCaP prostate cancer cells by suppression of Bcl-2 expression and the mTOR pathway.

Journal: Journal of agricultural and food chemistry 20090923

Title: Antimalarial pharmacodynamics of chalcone derivatives in combination with artemisinin against Plasmodium falciparum in vitro.

Journal: European journal of medicinal chemistry 20090901

Title: Inhibitory effect of chalcones and their derivatives from Glycyrrhiza inflata on protein tyrosine phosphatase 1B.

Journal: Bioorganic & medicinal chemistry letters 20090901

Title: Licochalcone A significantly suppresses LPS signaling pathway through the inhibition of NF-kappaB p65 phosphorylation at serine 276.

Journal: Cellular signalling 20090501

Title: Glycyrrhiza inflata-derived chalcones, Licochalcone A, Licochalcone B and Licochalcone D, inhibit phosphorylation of NF-kappaB p65 in LPS signaling pathway.

Journal: International immunopharmacology 20090401

Title: Phytochemical licochalcone A enhances antimalarial activity of artemisinin in vitro.

Journal: Acta tropica 20090301

Title: Licochalcone A is a potent inhibitor of TEL-Jak2-mediated transformation through the specific inhibition of Stat3 activation.

Journal: Biochemical pharmacology 20081215

Title: Structure and properties of licochalcone A-human serum albumin complexes in solution: a spectroscopic, photophysical and computational approach to understand drug-protein interaction.

Journal: Physical chemistry chemical physics : PCCP 20081128

Title: Functionalized chalcones with basic functionalities have antibacterial activity against drug sensitive Staphylococcus aureus.

Journal: European journal of medicinal chemistry 20080801

Title: Licochalcone A inhibits the growth of colon carcinoma and attenuates cisplatin-induced toxicity without a loss of chemotherapeutic efficacy in mice.

Journal: Basic & clinical pharmacology & toxicology 20080701

Title: 2-(3-aryl-3-oxopropen-1-yl)-9-tert-butyl-paullones: a new antileishmanial chemotype.

Journal: Journal of medicinal chemistry 20080214

Title: Antispasmodic activity of licochalcone A, a species-specific ingredient of Glycyrrhiza inflata roots.

Journal: The Journal of pharmacy and pharmacology 20071001

Title: Constituent properties of licorices derived from Glycyrrhiza uralensis, G. glabra, or G. inflata identified by genetic information.

Journal: Biological & pharmaceutical bulletin 20070701

Title: Topoisomerase I inhibition and cytotoxicity of licochalcones A and E from Glycyrrhiza inflata.

Journal: Archives of pharmacal research 20070301

Title: Anti-inflammatory efficacy of Licochalcone A: correlation of clinical potency and in vitro effects.

Journal: Archives of dermatological research 20060601

Title: Inhibition by licochalcone A, a novel flavonoid isolated from liquorice root, of IL-1beta-induced PGE2 production in human skin fibroblasts.

Journal: The Journal of pharmacy and pharmacology 20051201

Title: Parasite mitochondria as a target of chemotherapy: inhibitory effect of licochalcone A on the Plasmodium falciparum respiratory chain.

Journal: Annals of the New York Academy of Sciences 20051101

Title: Cationic chalcone antibiotics. Design, synthesis, and mechanism of action.

Journal: Journal of medicinal chemistry 20050407

Title: Synthesis of prenylated benzaldehydes and their use in the synthesis of analogues of licochalcone A.

Journal: European journal of medicinal chemistry 20041101

Title: Licochalcone-A, a novel flavonoid isolated from licorice root (Glycyrrhiza glabra), causes G2 and late-G1 arrests in androgen-independent PC-3 prostate cancer cells.

Journal: Biochemical and biophysical research communications 20040910

Title: Isolation and purification of inflacoumarin A and licochalcone A from licorice by high-speed counter-current chromatography.

Journal: Journal of chromatography. A 20040903

Title: Natural antimycobacterial metabolites: current status.

Journal: Phytochemistry 20040401

Title: Transcriptional suppression of the HIV promoter by natural compounds.

Journal: Antiviral research 20030301

Title: In vitro antimycobacterial and antilegionella activity of licochalcone A from Chinese licorice roots.

Journal: Planta medica 20020501

Title: Chalcones from Chinese liquorice inhibit proliferation of T cells and production of cytokines.

Journal: International immunopharmacology 20020301

Title: Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.

Journal: Anticancer research 20000101

Title: Phenolic constituents of licorice. II. Structures of licopyranocoumarin, licoarylcoumarin and glisoflavone, and inhibitory effects of licorice phenolics on xanthine oxidase.

Journal: Chemical & pharmaceutical bulletin 19891101

Title: Anti-human immunodeficiency virus phenolics from licorice.

Journal: Chemical & pharmaceutical bulletin 19880601

Title: Tang ZH, et al. Induction of C/EBP homologous protein-mediated apoptosis and autophagy by licochalcone A in non-small cell lung cancer cells. Sci Rep. 2016 May 17;6:26241.

Title: Hong Xin, et al. Assessment of the inhibition potential of Licochalcone A against human UDP-glucuronosyltransferases. Food and Chemical ToxicologyVolume 90, April 2016, Pages 112–122

Title: Egler J, et al. Licochalcone A Induced Suicidal Death of Human Erythrocytes. Cell Physiol Biochem. 2015;37(5):2060-70.

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Tags:58749-22-7 Molecular Formula|58749-22-7 MDL|58749-22-7 SMILES|58749-22-7 Licochalcone A