2H-pyran-2-one, 4-methoxy-6-(2-(4-methoxyphenyl)ethenyl)-, (E)- (9CI)

CAS: 500-62-9 C15 H14 O4 MW: 258.27338000

Identification

Nameyangonin
IUPAC4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one
CAS Number500-62-9
FDA UNIIR970U49V3C
Molecular FormulaC15 H14 O4
Molecular Weight258.27338000
MDL NumberMFCD00221733
Nikkaji NumberJ6.190E

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 156.00 °C. @ 760.00 mm Hg
Boiling Point 487.60 °C. @ 760.00 mm Hg (est)
Flash Point 427.00 °F. TCC ( 219.70 °C. ) (est)
logP (o/w) 1.750 (est)
Soluble in water, 816.4 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral Toxicityintraperitoneal-mouse LD50 > 1500 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for yangonin usage levels up tonot for fragrance use.
Recommendation for yangonin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

kava root

Synonyms

5- hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic acid d-lactone 5- hydroxy-3-methoxy-7-(para-methoxyphenyl)-2,4,6-heptatrienoic acid gamma-lactone (E)-4- methoxy-6-(2-(4-methoxyphenyl)ethenyl)-2H-pyran-2-one (E)-4- methoxy-6-(4-methoxystyryl)-2H-pyran-2-one 4- methoxy-6-(beta-(para-anisyl)vinyl)-alpha-pyrone 4- methoxy-6-(para-methoxystyryl)-2H-pyran-2-one 4- methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one 4- methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one 4- methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one (E)-4- methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one 4- methoxy-6-[b-(p-anisyl)vinyl]-a-pyrone 2H- pyran-2-one, 4-methoxy-6-(2-(4-methoxyphenyl)ethenyl)-, (E)- (9CI) 2H- pyran-2-one, 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]- 2H- pyran-2-one, 4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]-, (E)- PubMed: Phototoxicity of kava - formation of reactive oxygen species leading to lipid peroxidation and DNA damage. PubMed: Kavalactones and the endocannabinoid system: the plant-derived yangonin is a novel CB₁ receptor ligand. PubMed: Yangonin blocks tumor necrosis factor-α-induced nuclear factor-κB-dependent transcription by inhibiting the transactivation potential of the RelA/p65 subunit. PubMed: Kava components down-regulate expression of AR and AR splice variants and reduce growth in patient-derived prostate cancer xenografts in mice. PubMed: Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1. PubMed: Proposal for a kava quality standardization code. PubMed: Kavalactones Yangonin and Methysticin induce apoptosis in human hepatocytes (HepG2) in vitro. PubMed: Final report on the safety assessment of Piper methysticum leaf/root/stem extract and Piper methysticum root extract. PubMed: 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. PubMed: Evaluation of commercial kava extracts and kavalactone standards for mutagenicity and toxicity using the mammalian cell gene mutation assay in L5178Y mouse lymphoma cells. PubMed: Permeability studies of Kavalactones using a Caco-2 cell monolayer model. PubMed: Fourier transform ion cyclotron resonance mass spectrometry for the characterisation of kavalactones in the kava plant: elemental formulae confirmation by dual spray accurate mass measurement and structural confirmation by infrared multiphoton dissociation and sustained off-resonance irradiation collision induced dissociation. PubMed: Melanogenesis stimulation in murine B16 melanoma cells by Kava (Piper methysticum) rhizome extract and kavalactones. PubMed: Kavalactones fail to inhibit alcohol dehydrogenase in vitro. PubMed: Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro. PubMed: Superheated water chromatography-nuclear magnetic resonance spectroscopy of kava lactones. PubMed: Determination of kava lactones in food supplements by liquid chromatography-atmospheric pressure chemical ionisation tandem mass spectrometry. PubMed: Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard. PubMed: LC-UV and LC-MS analysis of food and drink products containing kava. PubMed: Analysis of kavalactones from Piper methysticum (kava-kava). PubMed: Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23. PubMed: Effects of kava (Kava-kava, 'Awa, Yaqona, Piper methysticum) on c-DNA-expressed cytochrome P450 enzymes and human cryopreserved hepatocytes. PubMed: Kava does not display metabolic toxicity in a homogeneous cellular assay. PubMed: In vitro toxicity of kava alkaloid, pipermethystine, in HepG2 cells compared to kavalactones. PubMed: Isolation and synthesis of TNF-alpha release inhibitors from Fijian kawa (Piper methysticum). PubMed: Effects of intrinsic fluorescence and quenching on fluorescence-based screening of natural products. PubMed: Cyclooxygenase enzyme inhibitory compounds with antioxidant activities from Piper methysticum (kava kava) roots. PubMed: Drug absorption in vitro model: filter-immobilized artificial membranes. 2. Studies of the permeability properties of lactones in Piper methysticum Forst. PubMed: Interaction of various Piper methysticum cultivars with CNS receptors in vitro. PubMed: Anxiolytic effects of kava extract and kavalactones in the chick social separation-stress paradigm. PubMed: Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava). PubMed: Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats. PubMed: Influence of genuine kavapyrone enantiomers on the GABA-A binding site. PubMed: Contribution to the quantitative and enantioselective determination of kavapyrones by high-performance liquid chromatography on ChiraSpher NT material. PubMed: Electrospray high performance liquid chromatography-mass spectrometry in phytochemical analysis of kava (Piper methysticum) extract. PubMed: Piper methysticum: enantiomeric separation of kavapyrones by high performance liquid chromatography. PubMed: Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodents. PubMed: Identification of some human urinary metabolites of the intoxicating beverage kava. PubMed: Uptake into mouse brain of four compounds present in the psychoactive beverage kava. PubMed: Metabolism of some kava pyrones in the rat. PubMed: [Quantitative determination of kawa lactones in Piper methysticum (Forster). 2. Determination of kawain, methysticin and yangonin]. PubMed: [Quantitative determination of kawa-lactones in Piper methysticum (Forster). 1. Determination methods with pure substances kawain, methysticin and yangonin]. PubMed: [Yangonin-a pharmacologically active pyran compound from Piper methysticum Forst]. PubMed: [11-methoxy-nor-yangonin from botanically undescribed piper plant species from New Guinea]. PubMed: [Isolation of 11-methoxy-yangonin from the cava root].