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

kavain
5,6-dihydro-4-methoxy-6-styryl-2H-pyran-2-one

Supplier Sponsors

Name:4-methoxy-2-(2-phenylethenyl)-2,3-dihydropyran-6-one
CAS Number: 500-64-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-907-2
FDA UNII: W1ES06373M
MDL:MFCD00270446
XlogP3-AA:2.50 (est)
Molecular Weight:230.26318000
Formula:C14 H14 O3
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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: 105.50 °C. @ 760.00 mm Hg
Boiling Point: 432.64 °C. @ 760.00 mm Hg (est)
Flash Point: 364.00 °F. TCC ( 184.60 °C. ) (est)
logP (o/w): 0.784 (est)
Soluble in:
 water, 1154 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.
Kavain 98%
BOC Sciences
For experimental / research use only.
Kavain ≥98%
Odor: characteristic
Use: Kavain is a kavalactone and the major constituent of the pepper plant kava (P. methysticum). Kavain has a positive modulatory e
Coompo
For experimental / research use only.
Kavain from Plants ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
Kavain (+/-)
 
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 420 mg/kg
BEHAVIORAL: ANTICONVULSANT
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969.

intravenous-mouse LD50 69 mg/kg
BEHAVIORAL: ANTICONVULSANT
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969.

oral-mouse LD50 1130 mg/kg
BEHAVIORAL: ANTICONVULSANT
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 kavain usage levels up to:
 not for fragrance use.
 
Recommendation for kavain flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10376
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-methoxy-2-(2-phenylethenyl)-2,3-dihydropyran-6-one
Chemidplus:0000500641
RTECS:UQ0518000 for cas# 500-64-1
 
References:
 4-methoxy-2-(2-phenylethenyl)-2,3-dihydropyran-6-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10376
Pubchem (sid):134978158
 
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
CHEMBL:View
KEGG (GenomeNet):C09947
HMDB (The Human Metabolome Database):HMDB34212
FooDB:FDB012515
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:
5,6-dihydro-4-methoxy-6-styryl-2H-pyran-2-one
 gonosan
5-hydroxy-3-methoxy-7-phenyl-2,6-heptadienoic acid gamma-lactone
 kawain
4-methoxy-2-(2-phenylethenyl)-2,3-dihydropyran-6-one
4-methoxy-6-(beta-phenyl vinyl)-5,6-dihydro-alpha-pyrone
4-methoxy-6-(beta-phenylvinyl)-5,6-dihydro-alpha-pyrone
 

Articles:

PubMed:Kavain analogues as potential analgesic agents.
PubMed:Phototoxicity of kava - formation of reactive oxygen species leading to lipid peroxidation and DNA damage.
PubMed:Kavalactone metabolism in rat liver microsomes.
PubMed:Standardless 1H NMR determination of pharmacologically active substances in dietary supplements and medicines that have been illegally traded over the internet.
PubMed:Pacific island 'Awa (Kava) extracts, but not isolated kavalactones, promote proinflammatory responses in model mast cells.
PubMed:Kavalactone metabolism in the isolated perfused rat liver.
PubMed:Kava components down-regulate expression of AR and AR splice variants and reduce growth in patient-derived prostate cancer xenografts in mice.
PubMed:Receptor activator of nuclear factor kappa B ligand antagonists inhibit tissue inflammation and bone loss in experimental periodontitis.
PubMed:Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1.
PubMed:Studies on the phase I metabolism of the new designer drug 3-fluoromethcathinone using rabbit liver slices.
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:Hypnotic and sleep quality-enhancing properties of kavain in sleep-disturbed rats.
PubMed:Identification and characterization of kava-derived compounds mediating TNF-alpha suppression.
PubMed:Analysis of toxic alkaloids in body samples.
PubMed:High-performance liquid chromatography assays for desmethoxyyangonin, methysticin, kavain and their microsomal metabolites.
PubMed:Enantioseparation of kavain on Chiralpak IA under normal-phase, polar organic and reversed-phase conditions.
PubMed:Effect of surfactants and solutes (glucose and NaCl) on solubility of Kavain--a technical note.
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:Efficient enantioselective hetero-Diels-Alder reaction of Brassard's diene with aliphatic aldehydes: a one-step synthesis of (R)-(+)-kavain and (S)-(+)-dihydrokavain.
PubMed:Influence of kavain on hepatic ultrastructure.
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:Comparison of the capabilities of accelerated solvent extraction and sonication as extraction techniques for the quantification of kavalactones in Piper methysticum (Kava) roots by high performance liquid chromatography with ultra violet detection.
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:[Acute hepatitis due to kava-kava and St John's Wort: an immune-mediated mechanism?].
PubMed:Melanogenesis stimulation in murine B16 melanoma cells by Kava (Piper methysticum) rhizome extract and kavalactones.
PubMed:Inhibition of TNFalpha-induced activation of nuclear factor kappaB by kava (Piper methysticum) derivatives.
PubMed:Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
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:Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice.
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 plant extracts by NIRS: simultaneous determination of kavapyrones and water in dry extracts of Piper methysticum Forst.
PubMed:Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23.
PubMed:Versatile asymmetric synthesis of the kavalactones: first synthesis of (+)-kavain.
PubMed:Testing for kavain in human hair using gas chromatography-tandem mass spectrometry.
PubMed:Kava lactones and the kava-kava controversy.
PubMed:Kinetics of kavain and its metabolites after oral application.
PubMed:Kava extract for treating anxiety.
PubMed:Adverse drug reaction update.
PubMed:Inhibition of cytochrome P450 3A4 by extracts and kavalactones of Piper methysticum (Kava-Kava).
PubMed:Inhibition of human cytochrome P450 activities by kava extract and kavalactones.
PubMed:Kavain attenuates vascular contractility through inhibition of calcium channels.
PubMed:Adverse drug reaction update.
PubMed:The neurobehavioural effects of kava.
PubMed:Densitometric analysis of kawain in kava-kava root extracts.
PubMed:Post-insult exposure to (+/-) kavain potentiates N-methyl-D-aspartate toxicity in the developing hippocampus.
PubMed:Kava extract for treating anxiety.
PubMed:Cyclooxygenase enzyme inhibitory compounds with antioxidant activities from Piper methysticum (kava kava) roots.
PubMed:Kava extract for treating anxiety.
PubMed:Drug absorption in vitro model: filter-immobilized artificial membranes. 2. Studies of the permeability properties of lactones in Piper methysticum Forst.
PubMed:Kava pyrones exert effects on neuronal transmission and transmembraneous cation currents similar to established mood stabilizers--a review.
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:Neuroprotective effects of (+/-)-kavain in the MPTP mouse model of Parkinson's disease.
PubMed:Microbial transformation of kawain and methysticin.
PubMed:Kavain inhibits murine airway smooth muscle contraction.
PubMed:Inhibitory effects of Alpinia speciosa K. SCHUM on the porphyrin photooxidative reaction.
PubMed:Evidence for specific interactions between kavain and human cortical neurons monitored by fluorescence correlation spectroscopy.
PubMed:Efficacy of kava extract for treating anxiety: systematic review and meta-analysis.
PubMed:Effects of (+/-)-kavain on voltage-activated inward currents of dorsal root ganglion cells from neonatal rats.
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:The influence of (+/-)-kavain on population spikes and long-term potentiation in guinea pig hippocampal slices.
PubMed:Influence of genuine kavapyrone enantiomers on the GABA-A binding site.
PubMed:In vivo effects of the kavapyrones (+)-dihydromethysticin and (+/-)-kavain on dopamine, 3,4-dihydroxyphenylacetic acid, serotonin and 5-hydroxyindoleacetic acid levels in striatal and cortical brain regions.
PubMed:Kavain, dihydrokavain, and dihydromethysticin non-competitively inhibit the specific binding of [3H]-batrachotoxinin-A 20-alpha-benzoate to receptor site 2 of voltage-gated Na+ channels.
PubMed:In vivo microdialysis study of (+/-)-kavain on veratridine-induced glutamate release.
PubMed:Contribution to the quantitative and enantioselective determination of kavapyrones by high-performance liquid chromatography on ChiraSpher NT material.
PubMed:[3H]-monoamine uptake inhibition properties of kava pyrones.
PubMed:Kava extract ingredients, (+)-methysticin and (+/-)-kavain inhibit voltage-operated Na(+)-channels in rat CA1 hippocampal neurons.
PubMed:Relaxation of evoked contractile activity of isolated guinea-pig ileum by (+/-)-kavain.
PubMed:Reduction of the frequency of occurrence of low magnesium induced field potentials in the hippocampus slice preparation of guinea pigs: a good screening tool for calcium antagonistic effects of anticonvulsant and antipsychotic drugs.
PubMed:Effects of kawain and dihydromethysticin on field potential changes in the hippocampus.
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:Antithrombotic action of the kava pyrone (+)-kavain prepared from Piper methysticum on human platelets.
PubMed:Kavain inhibits non-stereospecifically veratridine-activated Na+ channels.
PubMed:Anticonvulsive action of (+/-)-kavain estimated from its properties on stimulated synaptosomes and Na+ channel receptor sites.
PubMed:(+/-)-kavain inhibits the veratridine- and KCl-induced increase in intracellular Ca2+ and glutamate-release of rat cerebrocortical synaptosomes.
PubMed:The protective action of tetrodotoxin and (+/-)-kavain on anaerobic glycolysis, ATP content and intracellular Na+ and Ca2+ of anoxic brain vesicles.
PubMed:(+/-)-Kavain inhibits veratridine-activated voltage-dependent Na(+)-channels in synaptosomes prepared from rat cerebral cortex.
PubMed:Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodents.
PubMed:[Demonstration of the central effects of D,L-kawain with EEG brain mapping].
PubMed:[The action profile of D,L-kavain. Cerebral sites and sleep-wakefulness-rhythm in animals].
PubMed:Mass spectral characterization of urinary metabolites of D,L-kawain.
PubMed:The antinociceptive actions of kava components in mice.
PubMed:[D,L-kavain in comparison with oxazepam in anxiety disorders. A double-blind study of clinical effectiveness].
PubMed:The efficacy of Cavain in patients suffering from anxiety.
PubMed:Uptake into mouse brain of four compounds present in the psychoactive beverage kava.
PubMed:The effects of D, L-Kavain.
PubMed:Metabolism of some kava pyrones in the rat.
PubMed:[On the effect of d,l-kavain: experience with neuronika (author's transl)].
PubMed:Synthesis of kavain, dihydrokavain, and analogues.
PubMed:[Effect of kavain on alcoholic patients in the withdrawal phase (author's transl)].
PubMed:[Mental effects of kavain].
PubMed:[Synthesis of racemic 5,6-cis- and trans-kavain-5-ol].
PubMed:[Studies of the vegetative action mechanism of kavain and magnesium orotate].
PubMed:[The therapeutic effect of kavain and magnesium orotate on traumatic and vascular brain lesions].
PubMed:[Studies of the vegetative action mechanism of kavain and magnesium orotate].
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:[Kavain as a psychopharmacologic agent].
PubMed:[Kavain in diseases of the aged].
PubMed:Synthesis of kawain.
 
Notes:
Found in the roots of kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002)
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