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500-62-9,MFCD00221733
Catalog No.:AA019FQ9

500-62-9 | Yangonin

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Purity
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1mg
≥98%
in stock  
$89.00   $62.00
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25mg
95%
in stock  
$220.00   $154.00
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100mg
95%
in stock  
$665.00   $465.00
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250mg
95%
in stock  
$1,474.00   $1,032.00
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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:
AA019FQ9
Chemical Name:
Yangonin
CAS Number:
500-62-9
Molecular Formula:
C15H14O4
Molecular Weight:
258.2693
MDL Number:
MFCD00221733
SMILES:
COc1ccc(cc1)/C=C/c1cc(OC)cc(=O)o1
Properties
Properties
 
BP:
487.6°C at 760 mmHg  
Form:
Solid  
MP:
153-156ºC  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
412  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
4  
Rotatable Bond Count:
4  
XLogP3:
2.7  

Downstream Synthesis Route
334-88-3   
CASUnavailable 
  193353-03-6    500-62-9 

[1]Chmielewska;Cieslak[Bulletindel'AcademiePolonaisedesSciences,SeriedesSciencesChimiques,1953,vol.<III>1,p.257]

500-62-9   
CASUnavailable 

[1]Borsche;Blount[ChemischeBerichte,1932,vol.65,p.820,827]

[1]Bacardit,R.;Moreno-Manas,M.;Pleixats,R.[JournalofHeterocyclicChemistry,1982,vol.19,p.157-160]

[1]Lygo,Barry[Tetrahedron,1995,vol.51,#47,p.12859-12868]

Literature

Title: Yangonin protects against cholestasis and hepatotoxity via activation of farnesoid X receptor in vivo and in vitro.

Journal: Toxicology and applied pharmacology 20180601

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Yangonin blocks tumor necrosis factor-α-induced nuclear factor-κB-dependent transcription by inhibiting the transactivation potential of the RelA/p65 subunit.

Journal: Journal of pharmacological sciences 20120101

Title: Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20111201

Title: Kavalactones Yangonin and Methysticin induce apoptosis in human hepatocytes (HepG2) in vitro.

Journal: Phytotherapy research : PTR 20110301

Title: Anti-influenza activity of marchantins, macrocyclic bisbibenzyls contained in liverworts.

Journal: PloS one 20110101

Title: Final report on the safety assessment of Piper methysticum leaf/root/stem extract and Piper methysticum root extract.

Journal: International journal of toxicology 20090101

Title: Permeability studies of Kavalactones using a Caco-2 cell monolayer model.

Journal: Journal of clinical pharmacy and therapeutics 20070601

Title: Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).

Journal: Journal of agricultural and food chemistry 20060208

Title: Kavalactones fail to inhibit alcohol dehydrogenase in vitro.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20060201

Title: Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard.

Journal: Journal of AOAC International 20050101

Title: Superheated water chromatography-nuclear magnetic resonance spectroscopy of kava lactones.

Journal: Phytochemical analysis : PCA 20050101

Title: In vitro toxicity of kava alkaloid, pipermethystine, in HepG2 cells compared to kavalactones.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20040501

Title: Kava does not display metabolic toxicity in a homogeneous cellular assay.

Journal: Planta medica 20040401

Title: Effects of kava (Kava-kava, 'Awa, Yaqona, Piper methysticum) on c-DNA-expressed cytochrome P450 enzymes and human cryopreserved hepatocytes.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20040101

Title: Isolation and synthesis of TNF-alpha release inhibitors from Fijian kawa (Piper methysticum).

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20030501

Title: Effects of intrinsic fluorescence and quenching on fluorescence-based screening of natural products.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20020401

Title: Interaction of various Piper methysticum cultivars with CNS receptors in vitro.

Journal: Planta medica 20010601

Title: Ligresti A, et al. Kavalactones and the endocannabinoid system: the plant-derived yangonin is a novel CB1 receptor ligand. Pharmacol Res. 2012 Aug;66(2):163-9.

Title: Ma J, et al. Yangonin blocks tumor necrosis factor-α-induced nuclear factor-κB-dependent transcription by inhibiting the transactivation potential of the RelA/p65 subunit. J Pharmacol Sci. 2012;118(4):447-54.

Title: Wruck CJ, et al. Kavalactones protect neural cells against amyloid beta peptide-induced neurotoxicity via extracellular signal-regulated kinase 1/2-dependent nuclear factor erythroid 2-related factor 2 activation. Mol Pharmacol. 2008 Jun;73(6):1785-95.

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