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methysticin
kavahin

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Name:(2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
CAS Number: 495-85-2Picture of molecule3D/inchi
FDA UNII: M832AIJ6HX
Nikkaji Web:J6.085B
Beilstein Number:0091701
XlogP3-AA:2.40 (est)
Molecular Weight:274.27258000
Formula:C15 H14 O5
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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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 582 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Methysticin ≥98%
Odor: characteristic
Use: Methysticin is a natural kavalactone found in the kava plant. It induces hepatic CYP1A1 enzyme. Study in a mouse model of Alzhe A lactone isolated from the Kava plant (Piper methysticum).
 
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 530 mg/kg
BEHAVIORAL: ANTICONVULSANT
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969.

intravenous-mouse LD50 49 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 methysticin usage levels up to:
 not for fragrance use.
 
Recommendation for methysticin 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 :5281567
National Institute of Allergy and Infectious Diseases:Data
(2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
Chemidplus:0000495852
 
References:
 (2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281567
Pubchem (cas):495-85-2
 
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):C09952
HMDB (The Human Metabolome Database):HMDB33590
FooDB:FDB011667
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
Search Trop Picture
 
Synonyms:
(R-(E))-6-(2-(1,3-benzodioxol-5-yl)ethenyl)-5,6-dihydro-4-methoxy-2H-pyran-2-one
(2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
(R)-5,6-dihydro-4-methoxy-6-(3,4-(methylene dioxy)styryl)-2H-pyran-2-one
5-hydroxy-3-methoxy-7-(3,4-(methylenedioxy)phenyl)-2,6-heptadienoic acid gamma-lactone
 kavahin
 kavatin
2H-pyran-2-one, 5,6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)styryl)-, (R)-
 

Articles:

PubMed:Oral administration of methysticin improves cognitive deficits in a mouse model of Alzheimer's disease.
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:Kavalactones, a novel class of protein glycation and lipid peroxidation inhibitors.
PubMed:Phototoxicity of kava - formation of reactive oxygen species leading to lipid peroxidation and DNA damage.
PubMed:Kavalactone metabolism in rat liver microsomes.
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:Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1.
PubMed:Proposal for a kava quality standardization code.
PubMed:Herbal bioactivation, molecular targets and the toxicity relevance.
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:Highly regio- and stereoselective Heck reaction of allylic esters with arenediazonium salts: application to the synthesis of kavalactones.
PubMed:Identification of methysticin as a potent and non-toxic NF-kappaB inhibitor from kava, potentially responsible for kava's chemopreventive activity.
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: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:Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
PubMed:Kavalactones fail to inhibit alcohol dehydrogenase in vitro.
PubMed:Mass spectrometry-based screening for inhibitors of beta-amyloid protein aggregation.
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: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: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:Effects of herbal components on cDNA-expressed cytochrome P450 enzyme catalytic activity.
PubMed:Cyclooxygenase enzyme inhibitory compounds with antioxidant activities from Piper methysticum (kava kava) roots.
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:Microbial transformation of kawain and methysticin.
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:Kava extract ingredients, (+)-methysticin and (+/-)-kavain inhibit voltage-operated Na(+)-channels in rat CA1 hippocampal neurons.
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:Effects of methysticin on three different models of seizure like events studied in rat hippocampal and entorhinal cortex slices.
PubMed:Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodents.
PubMed:The antinociceptive actions of kava components in mice.
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].
 
Notes:
Found in kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002)
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