DihydrokavainCAS# 587-63-3 |
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| Cas No. | 587-63-3 | SDF | Download SDF |
| PubChem ID | 98356 | Appearance | White-pale yellow powder |
| Formula | C14H16O3 | M.Wt | 232.27 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Synonyms | 7,8-Dihydrokawain; 7,8-Dihydrokavain; Marindinin | ||
| Solubility | Freely soluble in dioxane and methanol; slightly soluble in water | ||
| Chemical Name | 4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one | ||
| SMILES | COC1=CC(=O)OC(C1)CCC2=CC=CC=C2 | ||
| Standard InChIKey | VOOYTQRREPYRIW-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Dihydrokavain may play an important role in regulation of GABAergic neurotransmission, it non-competitively inhibits the specific binding of [3H]-batrachotoxinin-A 20-alpha-benzoate to receptor site 2 of voltage-gated Na+ channels. Dihydrokavain may treat sleep disturbances, as well as stress and anxiety. |
| Targets | GABA Receptor | Sodium channel |
| In vitro | Kavalactones and dihydrokavain modulate GABAergic activity in a rat gastric-brainstem preparation.[Pubmed: 12494336]Planta Med. 2002 Dec;68(12):1092-6.
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| Kinase Assay | 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: 9690349]Planta Med. 1998 Jun;64(5):458-9.
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Dihydrokavain Dilution Calculator
Dihydrokavain Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.3053 mL | 21.5267 mL | 43.0533 mL | 86.1067 mL | 107.6334 mL |
| 5 mM | 0.8611 mL | 4.3053 mL | 8.6107 mL | 17.2213 mL | 21.5267 mL |
| 10 mM | 0.4305 mL | 2.1527 mL | 4.3053 mL | 8.6107 mL | 10.7633 mL |
| 50 mM | 0.0861 mL | 0.4305 mL | 0.8611 mL | 1.7221 mL | 2.1527 mL |
| 100 mM | 0.0431 mL | 0.2153 mL | 0.4305 mL | 0.8611 mL | 1.0763 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Dihydrokavain is one of the six major kavalactones found in the kava plant; appears to contribute significantly to the anxiolytic effects of kava, based on a study in chicks.
References:
[1]. Feltenstein MW, et al. Anxiolytic properties of Piper methysticum extract samples and fractions in the chick social-separation-stress procedure. Phytother Res. 2003 Mar;17(3):210-6.
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Kavalactones and dihydrokavain modulate GABAergic activity in a rat gastric-brainstem preparation.[Pubmed:12494336]
Planta Med. 2002 Dec;68(12):1092-6.
Using an in vitro neonatal rat gastric-brainstem preparation, the activity of majority neurons recorded in the nucleus tractus solitarius (NTS) of the brainstem were significantly inhibited by GABA A receptor agonist, muscimol (30 microM), and this inhibition was reversed by selective GABA A receptor antagonist, bicuculline (10 microM). Application of kavalactones (300 microg/ml) and Dihydrokavain (300 microM) into the brainstem compartment of the preparation also significantly reduced the discharge rate of these NTS neurons (39 % and 32 %, respectively, compared to the control level), and this reduction was partially reversed by bicuculline (10 microM). Kavalactones or Dihydrokavain induced inhibitory effects were not reduced after co-application of saclofen (10 microM; a selective GABA B receptor antagonist) or naloxone (100 nM; an opioid receptor antagonist). Pretreatment with kavalactones (300 microg/ml) or Dihydrokavain (300 microM) significantly decreased the NTS inhibitory effects induced by muscimol (30 microM), approximately from 51 % to 36 %. Our results demonstrated modulation of brainstem GABAergic mechanism by kavalactones and Dihydrokavain, and suggested that these compounds may play an important role in regulation of GABAergic neurotransmission.
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:9690349]
Planta Med. 1998 Jun;64(5):458-9.
The mode of action of the kava pyrones, kavain, Dihydrokavain and dihydromethysticin on the specific binding of [3H]-batrachotoxinin-A 20-alpha-benzoate to epitope 2 of voltage-dependent Na+ channels was investigated by performing saturation experiments in the presence and absence of these kava pyrones. The tested compounds significantly decreased the apparent total number of binding sites (Bmax) for [3H]-batrachotoxinin-A 20-alpha-benzoate (control: 0.5 pmol/mg protein, kava pyrones: 0.2-0.27 pmol/mg protein) with little change in the equilibrium constants (KD) for [3H]-batrachotoxin-A 20-alpha-benzoate (control: 28.2 nM, kava pyrones: 24-31 nM). The results indicate for the kava pyrones a non-competitive inhibition of the specific [3H]-batrachotoxinin-A 20-alpha-benzoate binding to receptor site 2 of voltage-gated Na+ channels.
