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MedKoo Cat#: 540255 | Name: Kawain

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Kawain voltage-gated Na+ and L-type Ca2+ channel blocker found in Puper methysticum (kava plant). It displays a variety of biological activities, including protecting against amyloid-β-induced neurotoxicity, suppressing growth of Fusarium, Trichoderma, and Colletotrichum, increasing non-REM sleep time and delta activity during REM sleep, and inhibiting arachidronic acid-induced platelet aggregation and COX expression.

Chemical Structure

Kawain
Kawain
CAS#3155-48-4

Theoretical Analysis

MedKoo Cat#: 540255

Name: Kawain

CAS#: 3155-48-4

Chemical Formula: C14H14O3

Exact Mass: 230.0943

Molecular Weight: 230.26

Elemental Analysis: C, 73.03; H, 6.13; O, 20.84

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
D,L-Kawin; Kawain
IUPAC/Chemical Name
(E)-4-methoxy-6-styryl-5,6-dihydro-2H-pyran-2-one
InChi Key
XEAQIWGXBXCYFX-BQYQJAHWSA-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+
SMILES Code
O=C1C=C(OC)CC(/C=C/C2=CC=CC=C2)O1
Appearance
Solid powder
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
>2 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
More Info

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.

Recalculate based on batch purity %
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
1: Upadhyay A, Tuenter E, Ahmad R, Amin A, Exarchou V, Apers S, Hermans N, Pieters L. Kavalactones, a novel class of protein glycation and lipid peroxidation inhibitors. Planta Med. 2014 Aug;80(12):1001-8. doi: 10.1055/s-0034-1382949. Epub 2014 Aug 6. PubMed PMID: 25098935. 2: Janeczko Z, Krzek J, Pilewski N, Walusiak D. Densitometric analysis of kawain in kava-kava root extracts. Acta Pol Pharm. 2001 Nov-Dec;58(6):463-8. PubMed PMID: 12197620. 3: Mathews JM, Etheridge AS, Valentine JL, Black SR, Coleman DP, Patel P, So J, Burka LT. Pharmacokinetics and disposition of the kavalactone kawain: interaction with kava extract and kavalactones in vivo and in vitro. Drug Metab Dispos. 2005 Oct;33(10):1555-63. Epub 2005 Jul 20. PubMed PMID: 16033948. 4: Walden J, von Wegerer J, Winter U, Berger M, Grunze H. Effects of kawain and dihydromethysticin on field potential changes in the hippocampus. Prog Neuropsychopharmacol Biol Psychiatry. 1997 May;21(4):697-706. PubMed PMID: 9194150. 5: Frey R. [Demonstration of the central effects of D,L-kawain with EEG brain mapping]. Fortschr Med. 1991 Aug 30;109(25):505-8. German. PubMed PMID: 1682226. 6: Abourashed EA, Khan IA. Microbial transformation of kawain and methysticin. Chem Pharm Bull (Tokyo). 2000 Dec;48(12):1996-8. PubMed PMID: 11145158. 7: 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. eCollection 2016. PubMed PMID: 27332705; PubMed Central PMCID: PMC4917254. 8: Köppel C, Tenczer J. Mass spectral characterization of urinary metabolites of D,L-kawain. J Chromatogr. 1991 Jan 2;562(1-2):207-11. PubMed PMID: 2026693. 9: Tang X, Amar S. Kavain Involvement in LPS-Induced Signaling Pathways. J Cell Biochem. 2016 Oct;117(10):2272-80. doi: 10.1002/jcb.25525. Epub 2016 Mar 9. PubMed PMID: 26917453. 10: Csupor L. [Quantitative determination of kawa lactones in Piper methysticum (Forster). 2. Determination of kawain, methysticin and yangonin]. Pharmazie. 1970 Mar;25(3):197-8. German. PubMed PMID: 5453803. 11: Tang X, Amar S. Kavain Inhibition of LPS-Induced TNF-α via ERK/LITAF. Toxicol Res (Camb). 2016 Jan 1;5(1):188-196. Epub 2015 Oct 21. PubMed PMID: 26918116; PubMed Central PMCID: PMC4764096. 12: Csupor L. [Quantitative determination of kawa-lactones in Piper methysticum (Forster). 1. Determination methods with pure substances kawain, methysticin and yangonin]. Arch Pharm Ber Dtsch Pharm Ges. 1970 Mar;303(3):193-200. German. PubMed PMID: 5267714. 13: Baum SS, Hill R, Rommelspacher H. Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Oct;22(7):1105-20. PubMed PMID: 9829291. 14: Li Y, Mei H, Wu Q, Zhang S, Fang JL, Shi L, Guo L. Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1. Toxicol Sci. 2011 Dec;124(2):388-99. doi: 10.1093/toxsci/kfr235. Epub 2011 Sep 9. PubMed PMID: 21908763. 15: Carlier J, Guitton J, Romeuf L, Bévalot F, Boyer B, Fanton L, Gaillard Y. Screening approach by ultra-high performance liquid chromatography-tandem mass spectrometry for the blood quantification of thirty-four toxic principles of plant origin. Application to forensic toxicology. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jan 15;975:65-76. doi: 10.1016/j.jchromb.2014.10.028. Epub 2014 Nov 1. PubMed PMID: 25438245. 16: Rasmussen AK, Scheline RR, Solheim E, Hänsel R. Metabolism of some kava pyrones in the rat. Xenobiotica. 1979 Jan;9(1):1-16. PubMed PMID: 760318. 17: Wang J, Qu W, Bittenbender HC, Li QX. Kavalactone content and chemotype of kava beverages prepared from roots and rhizomes of Isa and Mahakea varieties and extraction efficiency of kavalactones using different solvents. J Food Sci Technol. 2015 Feb;52(2):1164-9. doi: 10.1007/s13197-013-1047-2. Epub 2013 Jun 25. PubMed PMID: 25694734; PubMed Central PMCID: PMC4325077. 18: Whittaker P, Clarke JJ, San RH, Betz JM, Seifried HE, de Jager LS, Dunkel VC. Evaluation of commercial kava extracts and kavalactone standards for mutagenicity and toxicity using the mammalian cell gene mutation assay in L5178Y mouse lymphoma cells. Food Chem Toxicol. 2008 Jan;46(1):168-74. Epub 2007 Jul 31. PubMed PMID: 17822821. 19: Kormann EC, Amaral Pde A, David M, Eifler-Lima VL, Cechinel Filho V, Campos Buzzi F. Kavain analogues as potential analgesic agents. Pharmacol Rep. 2012;64(6):1419-26. PubMed PMID: 23406752. 20: Fu S, Rowe A, Ramzan I. Kavalactone metabolism in the isolated perfused rat liver. Phytother Res. 2012 Dec;26(12):1813-6. doi: 10.1002/ptr.4656. Epub 2012 Mar 9. PubMed PMID: 22407838.