Methysticin

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Methysticin
Methysticin.svg
Methysticin02.png
Names
IUPAC name
(2R)-2-[(E)-2-(1,3-Benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
Identifiers
495-85-2 YesY
ChemSpider 4444889 N
Jmol 3D model Interactive image
KEGG C09952 N
PubChem 5281567
  • InChI=1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1 N
    Key: GTEXBOVBADJOQH-FWEMWIAWSA-N N
  • InChI=1/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1
    Key: GTEXBOVBADJOQH-FWEMWIAWBD
  • COC1=CC(=O)O[C@H](C1)/C=C/C2=CC3=C(C=C2)OCO3
Properties
C15H14O5
Molar mass 274.27 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Methysticin is one of the six major kavalactones found in the kava plant.[1] Research suggests that methysticin and the related compound dihydromethysticin have CYP1A1 inducing effects which may be responsible for their toxicity.[2]

Toxicity

Methysticin induces the function of the hepatic enzyme CYP1A1, an enzyme involved in the toxification of benzo[a]pyrene into benzopyrene-7,8-dihydrodiol-9,10-epoxide, one of the most highly carcinogenic substances known. This property is shared by the related compound dihdromethysticin, both of which occur in significant quantities in Piper methysticum.[2][3][4]

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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