Dihydrokawain Chemical Properties

Melting point:

58-60°

alpha 

D24 +31° (methanol)

Boiling point:

314.44°C (rough estimate)

Density 

1.1649 (rough estimate)

refractive index 

1.5557 (estimate)

storage temp. 

2-8°C

solubility 

DMF:25.0(Max Conc. mg/mL);107.62(Max Conc. mM)
DMSO:25.0(Max Conc. mg/mL);107.62(Max Conc. mM)
Ethanol:5.0(Max Conc. mg/mL);21.52(Max Conc. mM)

optical activity

[α]/D 29±2°, c = 0.5 in methanol

BRN 

15362

InChIKey

VOOYTQRREPYRIW-LBPRGKRZSA-N

LogP

1.950 (est)

Safety Information

WGK Germany 

3

Dihydrokawain Usage And Synthesis

Chemical Properties

White-pale yellow powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from the rhizome of kava-kava (Piper methysticum G. Forst).

Uses

(+)-(S)-Dihydrokavain is a kavalactone found in kava beverages consumed by South Pacific islanders. Furthermore, roots and extracts of the kava plant have been used in herbal medicine to treat sleep disturbances, as well as stress and anxiety.

Definition

ChEBI: Dihydrokavain is a member of 2-pyranones and an aromatic ether.

Application

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.Used in herbal medicine to treat sleep disturbances, as well as stress and anxiety.

Preparation

Starting from 2,3-O-isopropylidene-D-glyceraldehyde (2) as chiral material, the naturally occurring (S)-(+)-dihydrokavain (1a) was synthesized by a procedure that involves a sonochemical Blaise reaction as the key step. The absolute configuration of (S)-(+)-dihydrokavain (1a) is demonstrated for the first time by total synthesis from a chiral source. Its opposite enantiomer, (R)-(–)-dihydrokavain (1b), was also synthesized after inversion of the chiral center in a Mitsunobu reaction.
A Total Synthesis of (+)- and (–)-Dihydrokavain with a Sonochemical Blaise Reaction as the Key Step

Dihydrokawain(587-63-3)Related Product Information

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