dihydrokawain

marindinin

CAS: 587-63-3 C14 H16 O3 MW: 232.27912000

Identification

Namedihydrokawain
IUPAC4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
CAS Number587-63-3
FDA UNIINW8ZGW9XRZ
Molecular FormulaC14 H16 O3
Molecular Weight232.27912000
MDL NumberMFCD01694032
Nikkaji NumberJ1.892.683K
Beilstein015362

Regulatory

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)

No sensory data available

Safety Information

Oral/Parenteral Toxicityintraperitoneal-cat LD50 > 250 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for dihydrokawain usage levels up tonot for fragrance use.
Recommendation for dihydrokawain flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

kava root

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- 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].