Dihydrokavain - CAS 587-63-3
Catalog number: 587-63-3
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
Molecular Weight:
Dihydrokavain is a kavalactone source from kava beverages used in herbal medicine to treat sleep disturbances, as well as stress and anxiety.
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(2S)-4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one; (+)-(S)-Dihydrokavain; 7,8-Dihydrokawain;
Soluble in DMSO
Store at -20 °C
Used in herbal medicine to treat sleep disturbances, as well as stress and anxiety.
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Melting Point:
57-59 °C
1.12 g/cm3
Canonical SMILES:
1.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.
Wang J1, Qu W2, Bittenbender HC3, Li QX4. J Food Sci Technol. 2015 Feb;52(2):1164-9. doi: 10.1007/s13197-013-1047-2. Epub 2013 Jun 25.
The South Pacific islanders have consumed kava beverage for thousands of years. The quality of kava and kava beverage is evaluated through determination of the content of six major kavalactones including methysticin, dihydromethysticin, kavain, dihydrokavain, yangonin and desmethoxyyangonin. In this study, we determined contents of kavalactones in and chemotype of kava beverages prepared from roots and rhizomes of Isa and Mahakea varieties and extraction efficiency of five different solvents including hexane, acetone, methanol, ethanol and ethyl acetate. The six major kavalactones were detected in all kava beverages with these five solvents. Different solvents had different extraction efficiencies for kavalactones from the lyophilized kava preparations. The contents of kavalactones in the extracts with acetone, ethanol, and methanol did not differ significantly. Ethanol had the highest extraction efficiency for the six major kavalactones whereas hexane gave the lowest extraction efficiency.
2.Dihydromethysticin from kava blocks tobacco carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis and differentially reduces DNA damage in A/J mice.
Narayanapillai SC1, Balbo S2, Leitzman P1, Grill AE2, Upadhyaya P2, Shaik AA3, Zhou B1, O'Sullivan MG4, Peterson LA5, Lu J6, Hecht SS7, Xing C8. Carcinogenesis. 2014 Oct;35(10):2365-72. doi: 10.1093/carcin/bgu149. Epub 2014 Jul 22.
We have previously shown that kava and its flavokavain-free Fraction B completely blocked 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung tumorigenesis in A/J mice with a preferential reduction in NNK-induced O (6)-methylguanine (O (6)-mG). In this study, we first identified natural (+)-dihydromethysticin (DHM) as a lead compound through evaluating the in vivo efficacy of five major compounds in Fraction B on reducing O (6)-mG in lung tissues. (+)-DHM demonstrated outstanding chemopreventive activity against NNK-induced lung tumorigenesis in A/J mice with 97% reduction of adenoma multiplicity at a dose of 0.05mg/g of diet (50 ppm). Synthetic (±)-DHM was equally effective as the natural (+)-DHM in these bioassays while a structurally similar analog, (+)-dihydrokavain (DHK), was completely inactive, revealing a sharp in vivo structure-activity relationship. Analyses of an expanded panel of NNK-induced DNA adducts revealed that DHM reduced a subset of DNA adducts in lung tissues derived from 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL, the active metabolite of NNK).
3.Identification of phytotoxic substances from early growth of barnyard grass (Echinochloa crusgalli) root exudates.
Xuan TD1, Chung IM, Khanh TD, Tawata S. J Chem Ecol. 2006 Apr;32(4):895-906. Epub 2006 May 5.
Barnyard grass is a problematic weed worldwide. It competes with crops and causes reduction in crop yields. In this study, barnyard grass suppressed rice emergence, and the degree of rice inhibition was proportional to the density of barnyard grass. Root exudates of barnyard grass reduced germination and growth of lettuce, rice, and monochoria. Fifteen compounds potentially involved in the phytotoxic activities of barnyard grass were isolated and identified, including phenolics, long-chain fatty acids, lactones, diethyl phthalate, acenaphthene, and derivatives of phthalic acids, benzoic acid, and decane. Quantities of diethyl phthalate, decanoic acid, myristic acid, stearic acid, 7,8-dihydro-5,6-dehydrokavain, and 7,8-dihydrokavain were 2.7, 11.1, 19.6, 35.5, 10.3, and 15.5 microg/ml of barnyard grass root exudates, respectively. The two lactones exhibited the greatest inhibition, followed by the phenolics and the derivatives of phthalic acids.
4.Cyclodextrins as carriers for kavalactones in aqueous media: spectroscopic characterization of (S)-7,8-dihydrokavain and beta-cyclodextrin inclusion complex.
Pescitelli G1, Bilia AR, Bergonzi MC, Vincieri FF, Di Bari L. J Pharm Biomed Anal. 2010 Aug 1;52(4):479-83. doi: 10.1016/j.jpba.2010.01.037. Epub 2010 Feb 1.
Kavalactones represent the active constituents of kava-kava (Piper methysticum G. Forster), endowed with sedative and anaesthetic properties. Kavalactones are polar constituents, but poorly soluble in water with a low bioavailability. In this study, the formation of inclusion complexes of one of the most representative kavalactone isolated from kava-kava extract, (S)-7,8-dihydrokavain (DHK), with beta-cyclodextrin (beta-CyD) was investigated mainly by spectroscopic methods. NMR experiments were extensively used for the complete characterization of the complex and included (1)H NMR complexation shifts analysis, (1)H NMR diffusion measurements (DOSY), and ROESY experiments. In particular DOSY experiments demonstrated that in the presence of beta-CyD the translational diffusion of kavalactone is sizably slowed down (2.5x10(-10)m(2)/s) with respect to the free drug (4.4x10(-10)m(2)/s) according to the inclusion of DHK in the cavity of (beta-CyD).
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CAS 587-63-3 Dihydrokavain

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