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Dihydrokavain

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Dihydrokavain
Chemical structure of dihydrokavain
An accurate three dimensional representation of the molecule of Dihydrokavain in ball-and-stick forma
Names
IUPAC name
4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
Other names
Dihydrokawain
Marindinin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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 ☒N
    Key: VOOYTQRREPYRIW-UHFFFAOYSA-N ☒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
  • COC1=CC(=O)OC(C1)CCC2=CC=CC=C2
Properties
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).
☒N verify (what is checkY☒N ?)

Dihydrokavain is one of the six major kavalactones found in the kava plant.[1] It appears to contribute significantly to the anxiolytic effects of kava, based on a study in chicks.[2]

Dihydrokavain bears some structural similarity to the strobilurins and has some fungicidal activity.[3]

An analogue of the molecule was also shown to improve glycemic control by modulating AMPK target genes expression in fruit flies.[4]

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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