Desmethoxyyangonin or 5,6-dehydrokavain is one of the six main kavalactones found in the Piper methysticum (kava) plant.
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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 | |
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Properties | |
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).
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Infobox references
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Desmethoxyyangonin is a reversible inhibitor of monoamine oxidase B (MAO-B).[1] Kava is able to increase dopamine levels in the nucleus accumbens[2] 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 GABAA receptor positive allosteric modulator.[3]
Desmethoxyyangonin has marked activity on the induction of CYP3A23.[4]
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