dihydromethysticin
methysticin, 7,8-dihydro-
Identification
| Name | dihydromethysticin |
| IUPAC | (2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one |
| CAS Number | 19902-91-1 |
| FDA UNII | FZ66MQ73GS |
| Molecular Formula | C15 H16 O5 |
| Molecular Weight | 276.28852000 |
| MDL Number | MFCD00221731 |
| Nikkaji Number | J816.005H |
| Beilstein | 091699 |
Regulatory
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) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | intraperitoneal-dog LD50 > 200 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 dihydromethysticin usage levels up to | not for fragrance use. |
| Recommendation for dihydromethysticin flavor usage levels up to | not for flavor use. |
BOC Sciences
Best of Chemicals Supplier
Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...
Potential Uses
Natural Occurrence
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)-
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].