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

dihydrokawain
marindinin

Supplier Sponsors

Name:4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
CAS Number: 587-63-3Picture of molecule3D/inchi
Other(deleted CASRN):19451-52-6
FDA UNII: NW8ZGW9XRZ
Nikkaji Web:J1.892.683K
Beilstein Number:015362
MDL:MFCD01694032
XlogP3-AA:2.80 (est)
Molecular Weight:232.27912000
Formula:C14 H16 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:
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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: 413.60 °C. @ 760.00 mm Hg (est)
Flash Point: 348.00 °F. TCC ( 175.60 °C. ) (est)
logP (o/w): 1.950 (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.
Dihydrokavain 98%
BOC Sciences
For experimental / research use only.
Dihydrokavain ≥95%
Odor: characteristic
Use: Dihydrokavain is a kavalactone source from kava beverages used in herbal medicine to treat sleep disturbances, as well as stress and anxiety. Used in herbal medicine to treat sleep disturbances, as well as stress and anxiety.
Coompo
For experimental / research use only.
Dihydrokavain from Plants ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
7,8-Dihydrokawain ≥98%
Sigma-Aldrich
For experimental / research use only.
(S)-(+)-7,8-Dihydrokavain
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-cat LD50 > 250 mg/kg
GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) BEHAVIORAL: MUSCLE WEAKNESS
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 505, 1962.

intraperitoneal-dog LD50 > 200 mg/kg
BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) GASTROINTESTINAL: NAUSEA OR VOMITING
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 505, 1962.

intraperitoneal-mouse LD50 325 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: ATAXIA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 505, 1962.

intravenous-mouse LD50 53 mg/kg
BEHAVIORAL: ANTICONVULSANT
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969.

oral-mouse LD50 920 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 138, Pg. 505, 1962.

intraperitoneal-rabbit LD50 350 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
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 dihydrokawain usage levels up to:
 not for fragrance use.
 
Recommendation for dihydrokawain 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 :98356
National Institute of Allergy and Infectious Diseases:Data
4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
Chemidplus:0000587633
 
References:
 4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):98356
Pubchem (sid):135057035
 
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
HMDB (The Human Metabolome Database):HMDB29504
FooDB:FDB000639
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:
(S)-5,6-dihydro-4-methoxy-6-(2-phenyl ethyl)-2H-pyran-2-one
5,6-dihydro-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one
 dihydrokavain
7,8-dihydrokawain
 kavain, dihydro-
 kawain, dihydro-
 marindinin
4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
4-methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
2H-pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethyl)-
2H-pyran-2-one, 5,6-dihydro-4-methoxy-6-phenethyl-
 

Articles:

PubMed:In vitro antitrypanosomal activity of some phenolic compounds from propolis and lactones from Fijian Kawa (Piper methysticum).
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:Cyclodextrins as carriers for kavalactones in aqueous media: spectroscopic characterization of (S)-7,8-dihydrokavain and beta-cyclodextrin inclusion complex.
PubMed:Identification and characterization of kava-derived compounds mediating TNF-alpha suppression.
PubMed:Intermolecular methoxycarbonylation of terminal alkynes catalyzed by palladium(II) bis(oxazoline) complexes.
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: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:Identification of phytotoxic substances from early growth of barnyard grass (Echinochloa crusgalli) root exudates.
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:Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein 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:Microbial metabolism. Part 5. Dihydrokawain.
PubMed:Enantioselective catalysis of the hetero-Diels-Alder reaction between Brassard's diene and aldehydes by hydrogen-bonding activation: a one-step synthesis of (S)-(+)-dihydrokawain.
PubMed:Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23.
PubMed:Facile one-step synthesis of beta-alkoxy lactone via sequential lactonization and 1,4-addition of alkoxide group: total synthesis of all stereoisomers of dihydrokawain-5-ol.
PubMed:Steviol quantification at the picomole level by high-performance liquid chromatography.
PubMed:Isolation and synthesis of TNF-alpha release inhibitors from Fijian kawa (Piper methysticum).
PubMed:Identification of novel electrophilic metabolites of piper methysticum Forst (Kava).
PubMed:Kinetics of kavain and its metabolites after oral application.
PubMed:Anxiolytic properties of Piper methysticum extract samples and fractions in the chick social-separation-stress procedure.
PubMed:Kavalactones and dihydrokavain modulate GABAergic activity in a rat gastric-brainstem preparation.
PubMed:Inhibition of cytochrome P450 3A4 by extracts and kavalactones of Piper methysticum (Kava-Kava).
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:Asymmetric synthesis of (+)-dihydrokawain-5-ol.
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: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: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:Uptake into mouse brain of four compounds present in the psychoactive beverage kava.
PubMed:Metabolism of some kava pyrones in the rat.
PubMed:Synthesis of kavain, dihydrokavain, and analogues.
PubMed:[INHIBITION OF ELECTROCONVULSION BY THE KAVA-PYRONES DIHYDROMETHYSTICIN AND DIHYDROKAVAIN].
PubMed:[The analgesic effect of kava constituents dihydrokavain and dihydromethysticine].
 
Notes:
inhibits binding of batrachotoxinin-a 20-alpha-benzoate to receptor site 2 of voltage-gated sodium channels. 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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