Desmethoxyyangonin

Desmethoxyyangonin

Names
Preferred IUPAC name 4-Methoxy-6-[(E)-2-phenylethen-1-yl]-2H-pyran-2-one
Other names (E)-4-Methoxy-6-styryl-2H-pyran-2-one 5,6-Dehydrokavain 4-Methoxy-6-[(E)-2-phenylvinyl]-2-pyranone
Identifiers
CAS Number	15345-89-8 Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL254218 Y
ChemSpider	4438012 Y
PubChem CID	5273621
UNII	F2MBQ8QRUN Y
CompTox Dashboard (EPA)	DTXSID4033390
InChI InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+ Y Key: DKKJNZYHGRUXBS-BQYQJAHWSA-N Y InChI=1/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+ Key: DKKJNZYHGRUXBS-BQYQJAHWBF
SMILES COC1=CC(=O)OC(=C1)C=CC2=CC=CC=C2 O=C/1O\C(=CC(\OC)=C\1)\C=C\c2ccccc2
Properties
Chemical formula	C14H12O3
Molar mass	228.247 g·mol−1
Appearance	white to faint yellow powder
Density	1.18 g/mL
Melting point	148 °C (298 °F; 421 K)
Boiling point	440 °C (824 °F; 713 K)
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

Desmethoxyyangonin or 5,6-dehydrokavain is one of the six main kavalactones found in the Piper methysticum (kava) plant.

Pharmacology

Desmethoxyyangonin is a reversible inhibitor of monoamine oxidase B (MAO-B). Kava is able to increase dopamine levels in the nucleus accumbens and desmethoxyyangonin likely contributes to this effect. This, along with several other catecholamines, may be responsible for the purported attention-promoting effects of kava.

Unlike the other major kavalactones, desmethoxyyangonin does not appear to act as a GABA_A receptor positive allosteric modulator.

Desmethoxyyangonin has marked activity on the induction of CYP3A23.

See also

• Kavain