Dihydrokavain

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,7-9H2,1H3 Key: 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,7-9H2,1H3 Key: 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 [77 °F], 100 kPa). verify (what is ?) Infobox references

Dihydrokavain is one of the six major kavalactones found in the kava plant. It showed the highest systemic exposure among all six major kavalactones tested, indicating it may play a central role in kava's pharmacological effects in humans. The anxiolytic effects of kava are primarily attributed to dihydrokavain.

In animal models, such as socially isolated chicks, dihydrokavain reduces anxiety-related distress without causing the sedation typically seen with standard anxiolytic drugs. Beyond its anxiolytic properties, dihydrokavain has demonstrated anti-inflammatory and analgesic effects, including inhibition of cyclooxygenase (COX) enzymes and suppression of tumor necrosis factor alpha (TNFα). It also shows potential anti-diabetic activity by activating AMP-activated protein kinase (AMPK) signaling and improving glycemic control in Drosophila models. Additionally, dihydrokavain inhibits several cytochrome P450 enzymes, indicating a potential for drug interactions, and shares structural similarities with strobilurins, contributing to mild fungicidal activity.