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| 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 | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| UNII | |
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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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Desmethoxyyangonin or5,6-dehydrokavain is one of the six mainkavalactones found in thePiper methysticum (kava) plant. It is a reversible inhibitor ofmonoamine oxidase B (MAO-B), likely contributing to increaseddopamine levels in the brain’snucleus accumbens and supporting kava’s attention-enhancing effects. Unlike otherkavalactones, it does not modulateGABAA receptors. It also strongly induces the liver enzymeCYP3A23. It is an active compound inAlpinia pricei with anti-inflammatory and liver-protective effects that improve survival in mice with endotoxin-induced hepatitis.
Desmethoxyyangonin is a reversibleinhibitor ofmonoamine oxidase B (MAO-B).[1] Kava is able to increasedopamine levels in thenucleus 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 aGABAA receptor positive allosteric modulator.[3]
Desmethoxyyangonin has marked activity on the induction of CYP3A23.[4]
It is an active compound in theFormosan plantAlpinia pricei and exhibits potentanti-inflammatory andhepatoprotective effects by inhibiting immune cell activation and key inflammatory signaling pathways, significantly improving survival and metabolic balance in mice with endotoxin-induced fulminanthepatitis.[5]
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