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

Hodoodo CAT#: H558158

CAS#: 587-63-3

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

Chemical Structure

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Dihydrokawain
CAS# 587-63-3
Instruction

Theoretical Analysis

Hodoodo Cat#: H558158
Name: Dihydrokawain
CAS#: 587-63-3
Chemical Formula: C14H16O3
Exact Mass: 232.11
Molecular Weight: 232.279
Elemental Analysis: C, 72.39; H, 6.94; O, 20.66

Price and Availability

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5mg USD 600 2 weeks
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Synonym: Dihydrokavain; Dihydrokawain; Kavain, dihydro-; 7,8-Dihydrokavain; (+)-Dihydrokawain; 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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 107.62
DMSO 25.0 107.62
Ethanol 5.0 21.52

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:
In vitro protocol:
In vivo protocol:

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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.

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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.