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HomeProduct name listDihydrokawain

Dihydrokawain

Synonym(s):(6S)-5,6-Dihydro-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one;7,8-Dihydrokawain;Dihydrokavain;Marindinin

  • CAS NO.:587-63-3
  • Empirical Formula: C14H16O3
  • Molecular Weight: 232.27
  • MDL number: MFCD01694032
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-04 20:04:50
Dihydrokawain Structural

What is Dihydrokawain?

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).

The Uses of Dihydrokawain

(+)-(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.

What are the applications of Application

7,8-Dihydrokawain is a compound that displays neuroprotective and antinociceptive activity

Definition

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

What are the applications of 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

Properties of Dihydrokawain

Melting point: 58-60°
Boiling point: 314.44°C (rough estimate)
alpha  D24 +31° (methanol)
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)
form  Solid
form  neat
color  White to off-white
optical activity [α]/D 29±2°, c = 0.5 in methanol
BRN  15362

Safety information for Dihydrokawain

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P501:Dispose of contents/container to..…

Computed Descriptors for Dihydrokawain

InChIKey VOOYTQRREPYRIW-LBPRGKRZSA-N

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