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MedKoo Cat#: 558158 | Name: Dihydrokawain
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Description:

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

Dihydrokawain inhibits binding of batrachotoxinin-A 20-alpha-benzoate to receptor site 2 of voltage-gated sodium channels.

Chemical Structure

Dihydrokawain
CAS#587-63-3

Theoretical Analysis

MedKoo Cat#: 558158

Name: Dihydrokawain

CAS#: 587-63-3

Chemical Formula: C14H16O3

Exact Mass: 232.1099

Molecular Weight: 232.28

Elemental Analysis: C, 72.39; H, 6.94; O, 20.66

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
Dihydrokavain; Dihydrokawain; Kavain, dihydro-; 7,8-Dihydrokavain; (+)-Dihydrokawain; Marindinin; NSC 112163; NSC-112163; NSC112163;
IUPAC/Chemical Name
(S)-4-methoxy-6-phenethyl-5,6-dihydro-2H-pyran-2-one
InChi Key
VOOYTQRREPYRIW-LBPRGKRZSA-N
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
SMILES Code
O=C1C=C(OC)C[C@H](CCC2=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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
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.
In vitro activity:
TBD
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMF 25.0 107.62
DMSO 25.0 107.62
Ethanol 5.0 21.52
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 232.28 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
Formulation protocol:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
1: Herath W, Ferreira D, Mikell JR, Khan IA. Microbial metabolism. Part 5. Dihydrokawain. Chem Pharm Bull (Tokyo). 2004 Nov;52(11):1372-4. PubMed PMID: 15516767. 2: Du H, Zhao D, Ding K. Enantioselective catalysis of the hetero-Diels-Alder reaction between Brassard's diene and aldehydes by hydrogen-bonding activation: a one-step synthesis of (S)-(+)-dihydrokawain. Chemistry. 2004 Nov 19;10(23):5964-70. Erratum in: Chemistry. 2005 Mar 18;11(7):1975. PubMed PMID: 15487027. 3: Singh RP, Singh VK. Facile one-step synthesis of beta-alkoxy lactone via sequential lactonization and 1,4-addition of alkoxide group: total synthesis of all stereoisomers of dihydrokawain-5-ol. J Org Chem. 2004 May 14;69(10):3425-30. PubMed PMID: 15132552. 4: Arai Y, Masuda T, Yoneda S, Masaki Y, Shiro M. Asymmetric synthesis of (+)-dihydrokawain-5-ol. J Org Chem. 2000 Jan 14;65(1):258-62. PubMed PMID: 10813926. 5: 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; PubMed Central PMCID: PMC5736320. 6: Otoguro K, Iwatsuki M, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Kiyohara H, Hashimoto T, Asakawa Y, Omura S, Yamada H. In vitro antitrypanosomal activity of some phenolic compounds from propolis and lactones from Fijian Kawa (Piper methysticum). J Nat Med. 2012 Jul;66(3):558-61. doi: 10.1007/s11418-011-0613-z. Epub 2011 Nov 25. PubMed PMID: 22116743. 7: Wu D, Yu L, Nair MG, DeWitt DL, Ramsewak RS. Cyclooxygenase enzyme inhibitory compounds with antioxidant activities from Piper methysticum (kava kava) roots. Phytomedicine. 2002 Jan;9(1):41-7. PubMed PMID: 11924763. 8: Häberlein H, Boonen G, Beck MA. Piper methysticum: enantiomeric separation of kavapyrones by high performance liquid chromatography. Planta Med. 1997 Feb;63(1):63-5. PubMed PMID: 17252330. 9: Keledjian J, Duffield PH, Jamieson DD, Lidgard RO, Duffield AM. Uptake into mouse brain of four compounds present in the psychoactive beverage kava. J Pharm Sci. 1988 Dec;77(12):1003-6. PubMed PMID: 3244102. 10: Jamieson DD, Duffield PH. The antinociceptive actions of kava components in mice. Clin Exp Pharmacol Physiol. 1990 Jul;17(7):495-507. PubMed PMID: 2401103. 11: 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. 12: Kato K, Motodate S, Mochida T, Kobayashi T, Akita H. Intermolecular methoxycarbonylation of terminal alkynes catalyzed by palladium(II) bis(oxazoline) complexes. Angew Chem Int Ed Engl. 2009;48(18):3326-8. doi: 10.1002/anie.200806080. PubMed PMID: 19191366. 13: Matthias A, Blanchfield JT, Penman KG, Bone KM, Toth I, Lehmann RP. Permeability studies of Kavalactones using a Caco-2 cell monolayer model. J Clin Pharm Ther. 2007 Jun;32(3):233-9. PubMed PMID: 17489874. 14: MEYER HJ, MEYER-BURG J. [INHIBITION OF ELECTROCONVULSION BY THE KAVA-PYRONES DIHYDROMETHYSTICIN AND DIHYDROKAVAIN]. Arch Int Pharmacodyn Ther. 1964 Mar 1;148:97-110. German. PubMed PMID: 14169874. 15: de Jager LS, Perfetti GA, Diachenko GW. LC-UV and LC-MS analysis of food and drink products containing kava. Food Addit Contam. 2004 Oct;21(10):921-34. PubMed PMID: 15712517. 16: Hashimoto T, Suganuma M, Fujiki H, Yamada M, Kohno T, Asakawa Y. Isolation and synthesis of TNF-alpha release inhibitors from Fijian kawa (Piper methysticum). Phytomedicine. 2003 May;10(4):309-17. PubMed PMID: 12809361. 17: MEYER HJ. [A STUDY OF THE ANTICONVULSANT PROPERTIES OF THE KAWA PYRONES DIHYDROMETHYSTICIN (DHM) AND DIHYROKAWAIN (DHK) IN CHEMICALLY INDUCED CONCLUSIONS]. Arch Int Pharmacodyn Ther. 1964 Jul 1;150:118-31. German. PubMed PMID: 14204485. 18: Ma Y, Sachdeva K, Liu J, Ford M, Yang D, Khan IA, Chichester CO, Yan B. Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23. Drug Metab Dispos. 2004 Nov;32(11):1317-24. Epub 2004 Jul 28. PubMed PMID: 15282211. 19: Backhauss C, Krieglstein J. Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodents. Eur J Pharmacol. 1992 May 14;215(2-3):265-9. PubMed PMID: 1396990. 20: 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.