CAS Number500-64-1
Synonyms4-Methoxy-6-(b-phenylvinyl)-5,6-dihydro-a-pyrone; 4-Methoxy-6-(β-phenylvinyl)-5,6-dihydro-α-pyrone; (R)-kavain; 5-Hydroxy-3-methoxy-7-phenyl-2,6-heptadienoic Acid d-Lactone; (+)-kavain; [R-(E)]-5,6-Dihydro-4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one; Kawain; Neuronika; Kavain; L-KAWAIN; Gonosan; (6R)-4-Methoxy-6-[(E)-2-phenylvinyl]-5,6-dihydro-2H-pyran-2-one; cavain; 5,6-Dihydro-4-methoxy-6-styryl-2H-pyran-2-one; 5,6-Dihydro-4-methoxy-6-styryl-2-pyron; (R)-5,6-Dihydro-4-methoxy-6-styryl-2H-pyran-2-one; D-Kawain; 4-Methoxy-6-styryl-5,6-dihydro-a-pyrone; (6R)-4-methoxy-6-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one
Molecular FormulaC14H14O3
Molecular Weight230.26
Purity98.00%
Density1.2±0.1 g/cm3
Boiling Point432.6±45.0 °C at 760 mmHg
Melting Point142-148ºC
AppearanceWhite, fine powder
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 500-64-1 |
| Catalog No. | 2A-9011093 |
| Chinese Name | 醉椒素 |
| Synonyms | 4-Methoxy-6-(b-phenylvinyl)-5,6-dihydro-a-pyrone; 4-Methoxy-6-(β-phenylvinyl)-5,6-dihydro-α-pyrone; (R)-kavain; 5-Hydroxy-3-methoxy-7-phenyl-2,6-heptadienoic Acid d-Lactone; (+)-kavain; [R-(E)]-5,6-Dihydro-4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one; Kawain; Neuronika; Kavain; L-KAWAIN; Gonosan; (6R)-4-Methoxy-6-[(E)-2-phenylvinyl]-5,6-dihydro-2H-pyran-2-one; cavain; 5,6-Dihydro-4-methoxy-6-styryl-2H-pyran-2-one; 5,6-Dihydro-4-methoxy-6-styryl-2-pyron; (R)-5,6-Dihydro-4-methoxy-6-styryl-2H-pyran-2-one; D-Kawain; 4-Methoxy-6-styryl-5,6-dihydro-a-pyrone; (6R)-4-methoxy-6-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one |
| Molecular Formula | C14H14O3 |
| Molecular Weight | 230.26 |
| Purity | 98.00 |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 432.6±45.0 °C at 760 mmHg |
| Melting Point | 142-148ºC |
| Appearance | White, fine powder |
| Storage Condition | -20℃ |
| Application | (+)-Kavain is a major kavalactone extracted from Kava pepper (Piper methysticum). It has anticonvulsant effects and weakens the contraction of vascular smooth muscle through the interaction of voltage |
| HTC | 2932999099 |
| MDL Number | MFCD00467093 |
| SMILES | O1[C@H](CC(=CC1=O)OC)\C=C\c2ccccc2 |
| InChI | 1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+/t12-/m0/s1 |
| InChI Key | XEAQIWGXBXCYFX-GUOLPTJISA-N |
| Beilstein/REAXYS | 1286081 |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| MSDS | msds/11093_1_500_64_1.pdf |
| Use of | (+)-Kavain, a main kavalactone extracted from Piper methysticum, has anticonvulsive properties, attenuating vascular smooth muscle contraction through interactions with voltage-dependent Na+ and Ca2+ channels[1]. (+)-Kavain is shown to bind at the α4β2δ GABAA receptor and potentiate GABA efficacy[2]. (+)-Kavain is used as a treatment for inflammatory diseases, its anti-inflammatory action has been widely studied[4]. Properties Name 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-styryl-, (+) Synonym More Synonyms Kawain Biological Activity Description (+)-Kavain, a main kavalactone extracted from Piper methysticum, has anticonvulsive properties, attenuating vascular smooth muscle contraction through interactions with voltage-dependent Na+ and Ca2+ channels[1]. (+)-Kavain is shown to bind at the α4β2δ GABAA receptor and potentiate GABA efficacy[2]. (+)-Kavain is used as a treatment for inflammatory diseases, its anti-inflammatory action has been widely studied[4]. Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor Signaling Pathways >> Neuronal Signaling >> GABA Receptor Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel Natural Products >> Flavonoids Research Areas >> Metabolic Disease Research Areas >> Neurological Disease Na+, Ca2+ channel[1]. α4β2δ GABAA receptor[2]. References [1]. Bradić I, et al. [Hirschsprung's disease -- therapy and results]. Acta Chir Iugosl. 1975;22(2):183-95. [2]. Chua HC, et al. Kavain, the Major Constituent of the Anxiolytic Kava Extract, Potentiates GABAA Receptors: Functional Characteristics and Molecular Mechanism. PLoS One. 2016 Jun 22;11(6):e0157700. [3]. G. Boonen, et al. 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. Planta Medica 64 (1998) 507-510. [4]. Tang X, et al. Kavain Inhibition of LPS-Induced TNF-α via ERK/LITAF. Toxicol Res (Camb). 2016 Jan 1;5(1):188-196. Chemical & Physical Properties Molecular Formula C14H14O3 Exact Mass 230.094299 PSA 35.53000 Index of Refraction 1.565 InChIKey XEAQIWGXBXCYFX-GUOLPTJISA-N Storage condition -20℃ Toxicological Information CHEMICAL IDENTIFICATION RTECS NUMBER : CHEMICAL NAME : 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-styryl-, (R)- CAS REGISTRY NUMBER : LAST UPDATED : DATA ITEMS CITED : MOLECULAR FORMULA : C14-H14-O3 MOLECULAR WEIGHT : WISWESSER LINE NOTATION : T6OV CUTJ DO1 F1U1R HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Behavioral - anticonvulsant REFERENCE : AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Behavioral - anticonvulsant REFERENCE : AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Behavioral - anticonvulsant REFERENCE : AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969 Safety Information Hazard Codes Xn Risk Phrases 22 HS Code 2932999099 |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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