yangonin
2H-pyran-2-one, 4-methoxy-6-(2-(4-methoxyphenyl)ethenyl)-, (E)- (9CI)
Identification
| Name | yangonin |
| IUPAC | 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one |
| CAS Number | 500-62-9 |
| FDA UNII | R970U49V3C |
| Molecular Formula | C15 H14 O4 |
| Molecular Weight | 258.27338000 |
| MDL Number | MFCD00221733 |
| Nikkaji Number | J6.190E |
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 Toxicity | intraperitoneal-mouse LD50 > 1500 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for yangonin usage levels up to | not for fragrance use. |
| Recommendation for yangonin flavor usage levels up to | not for flavor use. |
BOC Sciences
Best of Chemicals Supplier
Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...
Potential Uses
Natural Occurrence
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 CBâ 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].