Kawain

Names

[ CAS No. ]:
500-64-1

[ Name ]:
Kawain

[Synonym ]:
2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-[(E)-2-phenylethenyl]-, (6R)-
4-Methoxy-6-(b-phenylvinyl)-5,6-dihydro-a-pyrone
4-Methoxy-6-(β-phenylvinyl)-5,6-dihydro-α-pyrone
(R)-kavain
5-Hydroxy-3-methoxy-7-phenyl-2,6-heptadienoic Acid d-Lactone
(+)-kavain
[R-(E)]-5,6-Dihydro-4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one
2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-styryl-, (R)-
Kawain
Neuronika
Kavain
L-KAWAIN
Gonosan
(6R)-4-Methoxy-6-[(E)-2-phenylvinyl]-5,6-dihydro-2H-pyran-2-one
cavain
5,6-Dihydro-4-methoxy-6-styryl-2H-pyran-2-one
5,6-Dihydro-4-methoxy-6-styryl-2-pyron
(R)-5,6-Dihydro-4-methoxy-6-styryl-2H-pyran-2-one
D-Kawain
4-Methoxy-6-styryl-5,6-dihydro-a-pyrone
(6R)-4-methoxy-6-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one

Biological Activity

[Description]:

(+)-Kavain, a main kavalactone extracted from Piper methysticum, has anticonvulsive properties, attenuating vascular smooth muscle contraction through interactions with voltage-dependent Na+ and Ca2+ channels[1]. (+)-Kavain is shown to bind at the α4β2δ GABAA receptor and potentiate GABA efficacy[2]. (+)-Kavain is used as a treatment for inflammatory diseases, its anti-inflammatory action has been widely studied[4].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Natural Products >> Flavonoids

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

[Target]

Na+, Ca2+ channel[1]. α4β2δ GABAA receptor[2].

[In Vitro]

(+)-Kavain (10-300 μM) enhances GABA-elicited responses in a concentration-dependent manner. The modulatory effect of Kavain is moderate, with only 170±23% of enhancement measured at 300 μM[2]. (+)-Kavain inhibits TNF-α secretion in cells via suppression of LITAF[4].

[In Vivo]

[References]

[1]. Bradić I, et al. [Hirschsprung's disease -- therapy and results]. Acta Chir Iugosl. 1975;22(2):183-95.

[2]. Chua HC, et al. Kavain, the Major Constituent of the Anxiolytic Kava Extract, Potentiates GABAA Receptors: Functional Characteristics and Molecular Mechanism. PLoS One. 2016 Jun 22;11(6):e0157700.

[3]. G. Boonen, et al. In vivo Effects of the Kavapyrones (+)-Dihydromethysticin and (±)-Kavain on Dopamine, 3,4-Dihydroxyphenylacetic Acid, Serotonin and 5-Hydroxyindoleacetic Acid Levels in Striatal and Cortical Brain Regions. Planta Medica 64 (1998) 507-510.

[4]. Tang X, et al. Kavain Inhibition of LPS-Induced TNF-α via ERK/LITAF. Toxicol Res (Camb). 2016 Jan 1;5(1):188-196.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
432.6±45.0 °C at 760 mmHg

[ Melting Point ]:
142-148ºC

[ Molecular Formula ]:
C₁₄H₁₄O₃

[ Molecular Weight ]:
230.259

[ Flash Point ]:
184.6±23.3 °C

[ Exact Mass ]:
230.094299

[ PSA ]:
35.53000

[ LogP ]:
1.69

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

[ Index of Refraction ]:
1.565

[ Storage condition ]:
-20℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ0518000

CHEMICAL NAME :: 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-styryl-, (R)-

CAS REGISTRY NUMBER :: 500-64-1

LAST UPDATED :: 198706

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C14-H14-O3

MOLECULAR WEIGHT :: 230.28

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 :: 1130 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 :: Rodent - mouse

DOSE/DURATION :: 420 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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 69 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

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ HS Code ]:
2932999099

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%