Desmethoxyyangonin

Desmethoxyyangonin
Names
	IUPAC name 4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one
	Other names 5,6-Dehydrokawain; 4-methoxy-6-[(E)-2-phenylvinyl]-2-pyranone
Identifiers
CAS Number	15345-89-8 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL254218 ;
ChemSpider	4438012 ;
PubChem CID	5273621;
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+ Key: DKKJNZYHGRUXBS-BQYQJAHWSA-N ; 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). verify (what is ?) Infobox references

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

Pharmacology

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 the potential increases of serotonin and other catecholamine concentrations, may be responsible for the purported attention-promoting effects of kava.

Desmethoxyyangonin has marked activity on the induction of CYP3A23.^[3]

References

^ Uebelhack, R (September 1998). "Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava)". Pharmacopsychiatry. 31 (5): 187–192. doi:10.1055/s-2007-979325. PMID 9832350. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)CS1 maint: date and year (link)
^ Baum, SS (October 1998). "Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats". Progress in Neuro-Psychopharmacology and Biological Psychiatry. 22 (7): 1105–1120. doi:10.1016/S0278-5846(98)00062-1. PMID 9829291. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)CS1 maint: date and year (link)
^ Ma, Yuzhong (November 2004). "Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23". Drug Metabolism and Disposition. 32 (11): 1317–1324. doi:10.1124/dmd.104.000786. PMID 15282211. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

Pharmacology

References

See also