Desmethoxyyangonin

Names

[ Name ]:
Desmethoxyyangonin

[Synonym ]:
DIHYDROKAVAIN
2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-
2H-Pyran-2-one, 4-methoxy-6-[(E)-2-phenylethenyl]-
4-Methoxy-6-[(E)-2-phenylvinyl]-2H-pyran-2-one
4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one
Desmethoxyyangonin
(E)-4-Methoxy-6-(2-phenylethenyl)-2H-pyran-2-one,5,6-Dehydrokavain,Demethoxyyangonin

Biological Activity

[Description]:

Desmethoxyyangonin is one of the six major kavalactones found in the Piper methysticum (kava) plant; reversible inhibitor of MAO-B.

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase

Research Areas >> Others

Natural Products >> Others

[References]

[1]. Uebelhack R, et al. Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava). Pharmacopsychiatry. 1998 Sep;31(5):187-92.

[2]. Baum SS, et al. Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Oct;22(7):1105-20.

[3]. Ma Y, et al. Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23. Drug Metab Dispos. 2004 Nov;32(11):1317-24.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
440.0±45.0 °C at 760 mmHg

[ Melting Point ]:
138-140ºC

[ Molecular Formula ]:
C₁₄H₁₂O₃

[ Molecular Weight ]:
228.243

[ Flash Point ]:
188.0±23.3 °C

[ Exact Mass ]:
228.078644

[ PSA ]:
39.44000

[ LogP ]:
1.80

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.588

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ1240000

CHEMICAL NAME :: 2H-Pyran-2-one, 4-methoxy-6-styryl-, (E)-

CAS REGISTRY NUMBER :: 15345-89-8

LAST UPDATED :: 199206

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C14-H12-O3

MOLECULAR WEIGHT :: 228.26

WISWESSER LINE NOTATION :: T6OVJ DO1 F1U1R DO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 55 mg/kg

TOXIC EFFECTS :: Behavioral - anticonvulsant

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Articles

Fatal kavalactone intoxication by suicidal intravenous injection.

Forensic Sci. Int. 249 , e7-11, (2015)

Kavalactones are a group of compounds found in kava, a beverage or extract prepared from the rhizome of the kava plant (Piper methysticum). Traditionally kava extracts have been used for their anxioly...

Contribution to the quantitative and enantioselective determination of kavapyrones by high-performance liquid chromatography on ChiraSpher NT material.

J. Chromatogr. B. Biomed. Sci. Appl. 702(1-2) , 240-4, (1997)

A simultaneous HPLC separation of the enantiomers of kavain, dihydrokavain, methysticin and dihydromethysticin, as well as the achiral dienolides yangonin and desmethoxyyangonin was carried out on a C...

[Effects of the constituents of Alpinia speciosa rhizoma on experimental ulcers].

Taiwan Yi Xue Hui Za Zhi. 86(1) , 58-64, (1987)