methysticin
kavahin
Identification
| Name | methysticin |
| IUPAC | (2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one |
| CAS Number | 495-85-2 |
| FDA UNII | M832AIJ6HX |
| Molecular Formula | C15 H14 O5 |
| Molecular Weight | 274.27258000 |
| Nikkaji Number | J6.085B |
| Beilstein | 0091701 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 582 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 530 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 methysticin usage levels up to | not for fragrance use. |
| Recommendation for methysticin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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)-
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].