EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

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

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Name:4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one
CAS Number: 500-62-9Picture of molecule3D/inchi
FDA UNII: R970U49V3C
Nikkaji Web:J6.190E
MDL:MFCD00221733
XlogP3-AA:2.70 (est)
Molecular Weight:258.27338000
Formula:C15 H14 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Yangonin 98%
BOC Sciences
For experimental / research use only.
Yangonin ≥98%
Odor: characteristic
Use: Extract from Piper methysticum, enhancing the binding of bicuculline at the g-amino butyric acid. Enhances the binding of bicuculline
Coompo
For experimental / research use only.
Yangonin from Plants ≥95%
ExtraSynthese
For experimental / research use only.
Yangonin (HPLC) ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
Yangonin
Sigma-Aldrich
For experimental / research use only.
Yangonin
analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 > 1500 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969.

intravenous-mouse LD50 41 mg/kg
BEHAVIORAL: ANTICONVULSANT
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969.

oral-mouse LD50 > 1500 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281575
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one
Chemidplus:0000500629
 
References:
 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281575
Pubchem (sid):134978157
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09980
HMDB (The Human Metabolome Database):HMDB34144
FooDB:FDB012419
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 kava root
Search Trop Picture
 
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)-
 

Articles:

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].
 
Notes:
Found in kava root (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002)
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