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Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 476.10 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 417.00 °F. TCC ( 214.10 °C. ) (est)
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| logP (o/w): | 1.810 (est) |
| Soluble in: |
| | water, 582 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| 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.
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | natural substances and extractives |
| Recommendation for dihydromethysticin usage levels up to: | | | not for fragrance use.
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| Recommendation for dihydromethysticin flavor usage levels up to: |
| | not for flavor use.
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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:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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]. |
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