Methysticin

Methysticin

Names
IUPAC name (2R)-2-[(E)-2-(1,3-Benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
Identifiers
CAS Number	495-85-2 Y
ChemSpider	4444889 N
Jmol 3D model	Interactive image
KEGG	C09952 N
PubChem	5281567
InChI 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
SMILES COC1=CC(=O)O[C@H](C1)/C=C/C2=CC3=C(C=C2)OCO3
Properties
Chemical formula	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 YN ?)
Infobox references

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

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.