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Dihydrokawain

Dihydrokawain Structure
CAS No.
587-63-3
Chemical Name:
Dihydrokawain
Synonyms
MARINDININ;DIHYDROKAVAIN;DIHYDROKAWAIN;dihydro-kawai;DIHYDROKAWAIN;DIHYDROKAVAIN(P);7,8-Dihydrokavain;7,8-DIHYDROKAWAIN;(S)-(+)-7,8-Dihydrokavain;Dihydrokavain (7,8-Dihydrokawain
CBNumber:
CB4314738
Molecular Formula:
C14H16O3
Molecular Weight:
232.27
MOL File:
587-63-3.mol
MSDS File:
SDS
Modify Date:
2024/7/2 8:55:08

Dihydrokawain 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)
form Solid
color White to off-white
optical activity [α]/D 29±2°, c = 0.5 in methanol
BRN 15362
InChIKey VOOYTQRREPYRIW-LBPRGKRZSA-N
LogP 1.950 (est)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312+P330-P501
WGK Germany  3
NFPA 704
0
1 0

Dihydrokawain price More Price(1)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 41866 (S)-(+)-7,8-Dihydrokavain analytical standard 587-63-3 5MG ₹42618.03 2022-06-14 Buy
Product number Packaging Price Buy
41866 5MG ₹42618.03 Buy

Dihydrokawain Chemical Properties,Uses,Production

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

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(R)-5,6-Dihydro-4-methoxy-6-phenethyl-2H-pyran-2-one 4-Methoxy-6-phenethyl-5,6-dihydropyran-2-one 4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one (6S)-5,6-Dihydro-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one (S)-(+)-7,8-Dihydrokavain DIHYDROKAWAIN DIHYDROKAVAIN MARINDININ 7,8-DIHYDROKAWAIN 5,6-dihydro-4-methoxy-6-phenethyl-2h-pyran-2-on 7,8-Dihydrokavain Dihydrokavain (7,8-Dihydrokawain DIHYDROKAVAIN(P) 6-dihydro-4-methoxy-6-(2-phenylethyl)-(s)-2h-pyran-2-on dihydro-kawai (6R)-4-Methoxy-6-phenethyl-5,6-dihydro-2H-pyran-2-one Dihydrokavain, 98%, from Piper methysticum Forst 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethyl)-, (6S)- DIHYDROKAWAIN 587-63-3 Coumarins