Dihydromethysticin

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Dihydromethysticin
Chemical structure of dihydromethysticin
3D Chemical structure of dihydromethysticin
Names
IUPAC name
(2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
MeSH C107882
UNII
  • InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3
    Key: RSIWXFIBHXYNFM-UHFFFAOYSA-N
  • COC1=CC(=O)OC(C1)CCC2=CC3=C(C=C2)OCO3
Properties
C15H16O5
Molar mass 276.28 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dihydromethysticin is one of the six major kavalactones found in the kava plant.[1]

Pharmacology

Dihydromethysticin has marked activity on the induction of CYP3A23, as does the related chemical desmethoxyyangonin.[2]

Both dihydromethysticin and

benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide in the body (via the metabolism of benzo[a]pyrene) and may be responsible for some of the toxic effects associated with kava consumption.[citation needed
]

carcinogenic
benzo[a]pyren-7,8-dihydrodiol-9,10-epoxide.

positive allosteric modulator and as an reversible inhibitor of monoamine oxidase B.[4][5]

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. S2CID 43840844.{{cite journal}}: CS1 maint: numeric names: authors list (link
    )
  3. S2CID 34014477
    .
  4. S2CID 42935399
    .
  5. S2CID 34322458
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Dihydromethysticin&oldid=1129973667"