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desmethoxyyangonin
demethoxyyangonin

Supplier Sponsors

Name:4-methoxy-6-[(E)-2-phenylethenyl]pyran-2-one
CAS Number: 15345-89-8Picture of molecule3D/inchi
Other(deleted CASRN):26531-51-1
FDA UNII: F2MBQ8QRUN
Nikkaji Web:J81.846A
Beilstein Number:0181238
MDL:MFCD00221730
XlogP3-AA:2.80 (est)
Molecular Weight:228.24724000
Formula:C14 H12 O3
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
Boiling Point: 440.00 °C. @ 760.00 mm Hg (est)
Flash Point: 370.00 °F. TCC ( 188.00 °C. ) (est)
logP (o/w): 1.800 (est)
Soluble in:
 water, 1399 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.
Demethoxyyangonin 98%
BOC Sciences
For experimental / research use only.
Desmethoxyyangonin >98%
Odor: characteristic
Use: 5,6-Dehydrokawain is a phenolic compound found in the roots of Piper methysticum Forst. 5,6-Dehydrokawain is a reversible inhibitor of monoamine oxidase B.
Coompo
For experimental / research use only.
Desmethoxy Yangonin from Plants ≥98%
Sigma-Aldrich
For experimental / research use only.
Desmethoxyyangonin 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 > 800 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969.

intravenous-mouse LD50 55 mg/kg
BEHAVIORAL: ANTICONVULSANT
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969.

oral-mouse LD50 > 800 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
 
 
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 :5273621
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-methoxy-6-[(E)-2-phenylethenyl]pyran-2-one
Chemidplus:0015345898
 
References:
 4-methoxy-6-[(E)-2-phenylethenyl]pyran-2-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5273621
Pubchem (sid):135121040
 
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):C09925
HMDB (The Human Metabolome Database):Search
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
 found in nature
 
Synonyms:
 demethoxyyangonin
(E)-4-methoxy-6-(2-phenyl ethenyl)-2H-pyran-2-one
(E)-4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one
4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one
4-methoxy-6-[(E)-2-phenylethenyl]pyran-2-one
4-methoxy-6-[(E)-2-phenylvinyl]-2H-pyran-2-one
4-methoxy-6-styryl-(E)-2H-pyran-2-one
(E)-4-methoxy-6-styryl-2H-pyran-2-one
4-methoxy-6-styryl-2H-pyran-2-one
2H-pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (E)- (9CI)
2H-pyran-2-one, 4-methoxy-6-[(E)-2-phenylethenyl]-
 

Articles:

PubMed:Quantitative Determination of Lactones in Piper methysticum (Kava-Kava) by Supercritical Fluid Chromatography.
PubMed:Kavalactone content and chemotype of kava beverages prepared from roots and rhizomes of Isa and Mahakea varieties and extraction efficiency of kavalactones using different solvents.
PubMed:A plant kavalactone desmethoxyyangonin prevents inflammation and fulminant hepatitis in mice.
PubMed:Kavalactone metabolism in rat liver microsomes.
PubMed:Kavalactone metabolism in the isolated perfused rat liver.
PubMed:Proposal for a kava quality standardization code.
PubMed:High-performance liquid chromatography assays for desmethoxyyangonin, methysticin, kavain and their microsomal metabolites.
PubMed:Efficacy of extracting solvents to chemical components of kava (Piper methysticum) roots.
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:Determination of kava lactones and flavonoid glycoside in Scorzonera austriaca by capillary zone electrophoresis.
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:Pharmacokinetics and disposition of the kavalactone kawain: interaction with kava extract and kavalactones in vivo and 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:Antimycobacterial compounds from Piper sanctum.
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:Inhibition of human cytochrome P450 activities by kava extract and kavalactones.
PubMed:Effects of herbal components on cDNA-expressed cytochrome P450 enzyme catalytic activity.
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:Piper methysticum: enantiomeric separation of kavapyrones by high performance liquid chromatography.
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.
 
Notes:
None found
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