| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 100mg | |||
| Other Sizes |
| Targets |
Dihydrokawain inhibits cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2), as well as several cytochrome P450 enzymes, including CYP2C9 (IC50 = 130.95 µM), CYP2C19 (IC50 = 10.05 µM), and CYP3A4 (IC50 = 78.59 µM). It non-competitively inhibits the specific binding of [³H]-batrachotoxinin-A 20-alpha-benzoate to receptor site 2 of voltage-gated sodium channels. It also activates Nrf2 in neurons and astroglia, protecting against amyloid-β (Aβ)-induced neurotoxicity.
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| ln Vitro |
Dihydrokawain reduces TNFα secretion. It inhibits COX-1 and COX-2 enzymes. It also inhibits CYP2C9, CYP2C19, and CYP3A4 with IC50 values of 130.95 µM, 10.05 µM, and 78.59 µM, respectively. It non-competitively inhibits binding to voltage-gated sodium channels and activates Nrf2. These activities contribute to its anxiolytic, analgesic, and neuroprotective effects.
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| ln Vivo |
Dihydrokawain has been shown to activate Nrf2 in neurons and astroglia, protecting against amyloid-β (Aβ)-induced neurotoxicity in cellular models. It exhibits anxiolytic effects in the chick social-separation-stress procedure. It also inhibits glycine receptor activity in a dose-dependent manner. These in vivo and ex vivo studies support its traditional use as a calming and anti-anxiety agent.
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| Enzyme Assay |
In vitro enzyme assays for Dihydrokawain typically measure its inhibition of COX-1 and COX-2 activity, as well as its effects on cytochrome P450 enzymes (CYP2C9, CYP2C19, CYP3A4). The compound is incubated with the enzyme and a specific substrate, and the reaction products are quantified to determine IC50 values. Receptor binding assays can assess its interaction with voltage-gated sodium channels.
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| Cell Assay |
In vitro cellular assays for Dihydrokawain involve treating neuronal or other cell types with the compound to assess its effects on cell viability, neuroprotection, and signaling pathways. For example, its ability to activate Nrf2 and protect against Aβ-induced neurotoxicity can be evaluated in neuronal cell cultures. TNFα secretion can be measured by ELISA in treated immune cells.
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| Animal Protocol |
In vivo animal models for Dihydrokawain include the chick social-separation-stress procedure to assess its anxiolytic effects. In this model, chicks are separated from their flock, and the compound's ability to reduce distress vocalizations is measured. Other models may include rodent anxiety tests such as the elevated plus maze or open field test to evaluate its calming properties.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for Dihydrokawain are limited. As a kavalactone, it is expected to be absorbed after oral administration and metabolized in the liver, primarily by cytochrome P450 enzymes. Its inhibition of CYP enzymes may lead to drug-drug interactions. The compound's distribution and elimination half-life are not well-characterized, but it is known to cross the blood-brain barrier to exert its central nervous system effects.
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| Toxicity/Toxicokinetics |
Dihydrokawain is generally considered safe when consumed in moderate amounts as part of kava preparations. However, kava extracts have been associated with hepatotoxicity in rare cases, and the role of individual kavalactones in this toxicity is not fully understood. The compound may cause sedation and should not be combined with other central nervous system depressants.
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| References | |
| Additional Infomation |
Dihydrocarvaline belongs to the 2-pyranone class of compounds and is an aromatic ether. It has been reported to exist in Aniba hostmanniana, Piper majusculum, and other organisms with relevant data. See also: Root (part) of Piper methysticum.
Dihydrokawain is a natural kavalactone with anxiolytic and sedative properties. It inhibits COX-1, COX-2, and several CYP enzymes. It activates Nrf2 and protects against Aβ-induced neurotoxicity. It is found in kava preparations and has been studied for its calming effects and potential as a neuroprotective agent. It also inhibits glycine receptor activity. |
| Molecular Formula |
C14H16O3
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|---|---|
| Molecular Weight |
232.28
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| Exact Mass |
232.109
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| CAS # |
587-63-3
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| PubChem CID |
10220256
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
413.6±45.0 °C at 760 mmHg
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| Melting Point |
56-60ºC
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| Flash Point |
175.6±23.3 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.544
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| LogP |
1.95
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
17
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| Complexity |
290
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| Defined Atom Stereocenter Count |
1
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| SMILES |
COC1=CC(=O)O[C@H](C1)CCC2=CC=CC=C2
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| InChi Key |
VOOYTQRREPYRIW-LBPRGKRZSA-N
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| InChi Code |
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/t12-/m0/s1
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| Chemical Name |
(2S)-4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
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| Synonyms |
Kavain, dihydro-; Dihydrokawain; Dihydrokavain
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~430.51 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.76 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (10.76 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (10.76 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.3051 mL | 21.5257 mL | 43.0515 mL | |
| 5 mM | 0.8610 mL | 4.3051 mL | 8.6103 mL | |
| 10 mM | 0.4305 mL | 2.1526 mL | 4.3051 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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