Dihydrokavain

Names

[ CAS No. ]:
587-63-3

[ Name ]:
Dihydrokavain

[Synonym ]:
2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethyl)-
4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
Dihydrokavain
dihydrokawain
2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6- (2-phenylethyl)-, (S)-
(6S)-4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
5,6-Dihydro-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one
2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethyl)-, (6S)-

Biological Activity

[Description]:

Dihydrokavain is one of the six major kavalactones found in the kava plant; appears to contribute significantly to the anxiolytic effects of kava, based on a study in chicks.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Others

Research Areas >> Others

[References]

[1]. Feltenstein MW, et al. Anxiolytic properties of Piper methysticum extract samples and fractions in the chick social-separation-stress procedure. Phytother Res. 2003 Mar;17(3):210-6.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
413.6±45.0 °C at 760 mmHg

[ Melting Point ]:
56-60ºC

[ Molecular Formula ]:
C₁₄H₁₆O₃

[ Molecular Weight ]:
232.275

[ Flash Point ]:
175.6±23.3 °C

[ Exact Mass ]:
232.109940

[ PSA ]:
35.53000

[ LogP ]:
1.95

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.544

[ Storage condition ]:
-20℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ0517700

CHEMICAL NAME :: 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-phenethyl-

CAS REGISTRY NUMBER :: 587-63-3

LAST UPDATED :: 199206

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C14-H16-O3

MOLECULAR WEIGHT :: 232.30

WISWESSER LINE NOTATION :: T6OV CUTJ DO1 F1U1R

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 :: 920 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - other changes

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: 138,505,1962

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 325 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - other changes

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: 138,505,1962

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 53 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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >200 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Behavioral - muscle contraction or spasticity Gastrointestinal - nausea or vomiting

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: 138,505,1962

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: >250 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Behavioral - muscle contraction or spasticity Gastrointestinal - nausea or vomiting

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: 138,505,1962

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 350 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - muscle contraction or spasticity Lungs, Thorax, or Respiration - other changes

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: 138,505,1962

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Interaction of various Piper methysticum cultivars with CNS receptors in vitro.

Planta Med. 67(4) , 306-11, (2001)

Methanolic leaf and root extracts of the Hawaiian kava (Piper methysticum Forst.) cultivars, Mahakea, Nene, Purple Moi and PNG, were tested on binding affinities to CNS receptors including GABAA (GABA...

Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard.

J. AOAC Int. 88(1) , 16-25, (2005)

Kava (Piper methysticum) dietary products have been sold worldwide for treatment of nervous anxiety, tension, and restlessness. Recent reports showed potential association of kava usage and liver inju...

Glial dysfunction in the mouse habenula causes depressive-like behaviors and sleep disturbance.

J. Neurosci. 34(49) , 16273-85, (2014)

The lateral habenula (LHb) regulates the activity of monoaminergic neurons in the brainstem. This area has recently attracted a surge of interest in psychiatry because studies have reported the pathol...