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

dihydromethysticin
methysticin, 7,8-dihydro-

Supplier Sponsors

Name:(2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
CAS Number: 19902-91-1Picture of molecule3D/inchi
FDA UNII: FZ66MQ73GS
Nikkaji Web:J816.005H
Beilstein Number:091699
MDL:MFCD00221731
XlogP3-AA:2.60 (est)
Molecular Weight:276.28852000
Formula:C15 H16 O5
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
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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
Boiling Point: 476.10 °C. @ 760.00 mm Hg (est)
Flash Point: 417.00 °F. TCC ( 214.10 °C. ) (est)
logP (o/w): 1.810 (est)
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:
Alfa Biotechnology
For experimental / research use only.
Dihydromethysticin 98%
BOC Sciences
For experimental / research use only.
Dihydromethysticin 95%
Odor: characteristic
Use: Dihydromethysticin, found in the roots of kava plant, is one of the six major kavalactones used in toxicity studies through in vitro analysis.
Coompo
For experimental / research use only.
Dihydromethysticin from Plants ≥98%
Sigma-Aldrich
For experimental / research use only.
(+)-Dihydromethysticin
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-dog LD50 > 200 mg/kg
BEHAVIORAL: MUSCLE WEAKNESS GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 505, 1962.

intraperitoneal-mouse LD50 420 mg/kg
Experientia. Vol. 26, Pg. 283, 1970.

oral-mouse LD50 1050 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: ATAXIA BEHAVIORAL: MUSCLE WEAKNESS
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 505, 1962.

intraperitoneal-rabbit LD50 300 mg/kg
GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 505, 1962.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for dihydromethysticin usage levels up to:
 not for fragrance use.
 
Recommendation for dihydromethysticin 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 :88308
National Institute of Allergy and Infectious Diseases:Data
(2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
Chemidplus:0019902911
 
References:
 (2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):88308
Pubchem (sid):135046882
 
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):C09926
HMDB (The Human Metabolome Database):HMDB30791
FooDB:FDB002731
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:
(S)-6-(2-(1,3-benzodioxol-5-yl)ethyl)-5,6-dihydro-4-methoxy-2H-pyran-2-one
(2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
(6S)-6-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
7,8-dihydromethysticin
 methysticin, 7,8-dihydro-
2H-pyran-2-one, 5,6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)phenethyl)-, (S)-
2H-pyran-2-one, 6-(2-(1,3-benzodioxol-5-yl)ethyl)-5,6-dihydro-4-methoxy-, (S)- (9CI)
2H-pyran-2-one, 6-[2-(1,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-, (6S)-
 

Articles:

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: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:Highly regio- and stereoselective Heck reaction of allylic esters with arenediazonium salts: application to the synthesis of kavalactones.
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:Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
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: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:In vitro toxicity of kava alkaloid, pipermethystine, in HepG2 cells compared to kavalactones.
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: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: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: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:Contribution to the quantitative and enantioselective determination of kavapyrones by high-performance liquid chromatography on ChiraSpher NT material.
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: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:[Spasmolytic effect of dihydromethysticin, a constituent of Piper methysticum Forst].
PubMed:[A STUDY OF THE ANTICONVULSANT PROPERTIES OF THE KAWA PYRONES DIHYDROMETHYSTICIN (DHM) AND DIHYROKAWAIN (DHK) IN CHEMICALLY INDUCED CONCLUSIONS].
PubMed:[INHIBITION OF ELECTROCONVULSION BY THE KAVA-PYRONES DIHYDROMETHYSTICIN AND DIHYDROKAVAIN].
 
Notes:
Isol. from Piper methysticum (kava). FDA advises against use of kava in food due to potential risk of severe liver damage (2002) Dihydromethysticin is one of the six major kavalactones found in the kava plant.
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