Synonym
Kavain, Kawain, NSC 112162
IUPAC/Chemical Name
(6R)-5,6-dihydro-4-methoxy-6-[(1E)-2-phenylethenyl]-2H-pyran-2-one
InChi Key
XEAQIWGXBXCYFX-GUOLPTJISA-N
InChi Code
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
SMILES Code
O=C1O[C@@H](/C=C/C2=CC=CC=C2)CC(OC)=C1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
(+)-Kavain is shown to bind at the α4β2δ GABAA receptor and potentiate GABA efficacy.
In vitro activity:
This study characterised the functional properties of the major anxiolytic kavalactone, kavain at human recombinant α1β2, β2γ2L, αxβ2γ2L (x = 1, 2, 3 and 5), α1βxγ2L (x = 1, 2 and 3) and α4β2δ GABAARs expressed in Xenopus oocytes using the two-electrode voltage clamp technique. This study found that kavain positively modulated all receptors regardless of the subunit composition, but the degree of enhancement was greater at α4β2δ than at α1β2γ2L GABAARs.
Reference: PLoS One. 2016 Jun 22;11(6):e0157700. https://pubmed.ncbi.nlm.nih.gov/27332705/
In vivo activity:
Finally, in vivo, Kavain had a significant anti-inflammatory effect on wild type mice that developed Collagen Antibody Induced Arthritis (CAIA), but only a minor effect in ERK2-/- mice also affected by CAIA.
Reference: Toxicol Res (Camb). 2016 Jan 1;5(1):188-196. https://pubmed.ncbi.nlm.nih.gov/26918116/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
25.0 |
108.57 |
| DMSO |
37.5 |
162.86 |
| Ethanol |
5.0 |
0.87 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
230.26
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Vale Junior EPD, Ferreira MVR, Fernandes BCS, Silva TTD, Martins FA, Almeida PM. Protective effect of kavain in meristematic cells of Allium cepa L. An Acad Bras Cienc. 2022 Jun 13;94(2):e20200520. doi: 10.1590/0001-3765202220200520. PMID: 35703688.
2. Chua HC, Christensen ET, Hoestgaard-Jensen K, Hartiadi LY, Ramzan I, Jensen AA, Absalom NL, Chebib M. 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. doi: 10.1371/journal.pone.0157700. PMID: 27332705; PMCID: PMC4917254.
3. Singh SP, Huck O, Abraham NG, Amar S. Kavain Reduces Porphyromonas gingivalis-Induced Adipocyte Inflammation: Role of PGC-1α Signaling. J Immunol. 2018 Sep 1;201(5):1491-1499. doi: 10.4049/jimmunol.1800321. Epub 2018 Jul 23. Erratum in: J Immunol. 2021 Nov 1;207(9):2387. PMID: 30037847; PMCID: PMC6103801.
4. Tang X, Amar S. Kavain Inhibition of LPS-Induced TNF-α via ERK/LITAF. Toxicol Res (Camb). 2016 Jan 1;5(1):188-196. doi: 10.1039/C5TX00164A. Epub 2015 Oct 21. PMID: 26918116; PMCID: PMC4764096.
In vitro protocol:
1. Vale Junior EPD, Ferreira MVR, Fernandes BCS, Silva TTD, Martins FA, Almeida PM. Protective effect of kavain in meristematic cells of Allium cepa L. An Acad Bras Cienc. 2022 Jun 13;94(2):e20200520. doi: 10.1590/0001-3765202220200520. PMID: 35703688.
2. Chua HC, Christensen ET, Hoestgaard-Jensen K, Hartiadi LY, Ramzan I, Jensen AA, Absalom NL, Chebib M. 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. doi: 10.1371/journal.pone.0157700. PMID: 27332705; PMCID: PMC4917254.
In vivo protocol:
1. Singh SP, Huck O, Abraham NG, Amar S. Kavain Reduces Porphyromonas gingivalis-Induced Adipocyte Inflammation: Role of PGC-1α Signaling. J Immunol. 2018 Sep 1;201(5):1491-1499. doi: 10.4049/jimmunol.1800321. Epub 2018 Jul 23. Erratum in: J Immunol. 2021 Nov 1;207(9):2387. PMID: 30037847; PMCID: PMC6103801.
2. Tang X, Amar S. Kavain Inhibition of LPS-Induced TNF-α via ERK/LITAF. Toxicol Res (Camb). 2016 Jan 1;5(1):188-196. doi: 10.1039/C5TX00164A. Epub 2015 Oct 21. PMID: 26918116; PMCID: PMC4764096.
1. Chua, H.C., Christensen, E.T., Hoestgaard-Jensen, K., et al. Kavain, the major constituent of the anxiolytic kava extract, potentiates GABAA receptors: Functional characteristics and molecular mechanism. PLoS One 11(6), e0157700 (2016).
2. Li, X., Liu, Z., Xu, X., et al. Kava components down-regulate expression of AR and AR splice variants and reduce growth in patient-derived prostate cancer xenografts in mice. PLoS One 7(2), e31213 (2012).
3. Tang, X., and Amar, S. Kavain Inhibition of LPS-Induced TNF-α via ERK/LITAF. Toxicol. Res. (Camb). 5(1), 188-196 (2016).
4. Kormann, E.C., de Aguiar Amaral, P., David, M., et al. Kavain analogues as potential analgesic agents. Pharmacol. Rep. 64(6), 1419-1426 (2012).
