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Dihydrokavain

Names
IUPAC name 4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
Other names Dihydrokawain Marindinin
Identifiers
CAS Number	587-63-3
3D model (JSmol)	Interactive image
ChemSpider	88817
PubChem CID	98356
UNII	NW8ZGW9XRZ
CompTox Dashboard (EPA)	DTXSID101018162 DTXSID8033433, DTXSID101018162
InChI 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,7-9H2,1H3Key: VOOYTQRREPYRIW-UHFFFAOYSA-N InChI=1/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3Key: VOOYTQRREPYRIW-UHFFFAOYAX
SMILES COC1=CC(=O)OC(C1)CCC2=CC=CC=C2
Properties
Chemical formula	C14H16O3
Molar mass	232.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Dihydrokavain is one of the six major kavalactones found in the kava plant. It appears to contribute significantly to the anxiolytic effects of kava, based on a study in chicks.

Dihydrokavain bears some structural similarity to the strobilurins and has some fungicidal activity.

An analogue of the molecule was also shown to improve glycemic control by modulating AMPK target genes expression in fruit flies.

References

1. Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver" (PDF). Fiji School of Medicine. Archived from the original (PDF) on 2009-03-20. Retrieved 2009-09-04.
2. Feltenstein, MW; LC Lambdin; M Ganzera; H Ranjith; W Dharmaratne; NP Nanayakkara; IA Khan; KJ Sufka (March 2003). "Anxiolytic properties of Piper methysticum extract samples and fractions in the chick social-separation-stress procedure". Phytotherapy Research. 17 (3): 210–216. doi:10.1002/ptr.1107. PMID 12672148. S2CID 10548965.
3. Zakharychev, Vladimir V; Kovalenko, Leonid V (1998-06-30). "Natural compounds of the strobilurin series and their synthetic analogues as cell respiration inhibitors". Russian Chemical Reviews. 67 (6): 535–544. Bibcode:1998RuCRv..67..535Z. doi:10.1070/rc1998v067n06abeh000426. ISSN 0036-021X. S2CID 95676421.
4. Hadiza Muhammad Maiturare; Mudassir Aliyu Magaji; Muhammad Kabiru Dallatu; Kabir Magaji Hamid; Mustapha Umar Imam; Ibrahim Malami (2022). "5,6-dehydrokawain improves glycaemic control by modulating AMPK target genes in Drosophila with a high-sucrose diet-induced hyperglycaemia". Phytomedicine Plus. 2 (2): 100261–. doi:10.1016/j.phyplu.2022.100261. ISSN 2667-0313. S2CID 247649601.

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