587-63-3

Basic information

• Product Name: DIHYDROKAVAIN
• Synonyms: (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
• CAS NO: 587-63-3
• Molecular Formula: C₁₄H₁₆O₃
• Molecular Weight: 232.28
• Product Categories: Coumarins
• Mol File: 587-63-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 58-60°
• Boiling Point: 314.44°C (rough estimate)
• Flash Point: 175.6 ºC
• Appearance: White powder
• Density: 1.1649 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5557 (estimate)
• Storage Temp.: 2-8°C
• BRN: 15362
• CAS DataBase Reference: DIHYDROKAVAIN(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDROKAVAIN(587-63-3)
• EPA Substance Registry System: DIHYDROKAVAIN(587-63-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 587-63-3(Hazardous Substances Data)

Usage

Description

DIHYDROKAVAIN, also known as (+)-(S)-Dihydrokavain, is a kavalactone derived from the kava plant, which is native to the South Pacific. It is a member of the 2-pyranones and an aromatic ether, characterized by its white-pale yellow powder form. DIHYDROKAVAIN is soluble in various organic solvents such as methanol, ethanol, and DMSO. It is one of the six major kavalactones found in the kava plant and is known for its potential anxiolytic effects.

Uses

Used in Herbal Medicine:
DIHYDROKAVAIN is used as a therapeutic agent for treating sleep disturbances, stress, and anxiety. Its anxiolytic effects have been observed in studies, such as one conducted on chicks, which suggests that it contributes significantly to the overall calming properties of kava.
Used in the Beverage Industry:
DIHYDROKAVAIN is used as an active ingredient in kava beverages, which are consumed by South Pacific islanders. These beverages are known for their relaxing and stress-relieving properties, making them a popular choice for social and ceremonial occasions.
Used in Pharmaceutical Research:
Due to its potential anxiolytic effects, DIHYDROKAVAIN is also used as a subject of research in the pharmaceutical industry. Scientists are exploring its potential applications in the development of new drugs and therapies for anxiety and stress-related disorders.
Used in Dietary Supplements:
DIHYDROKAVAIN is used as an ingredient in dietary supplements that aim to promote relaxation, reduce stress, and improve sleep quality. These supplements are often marketed to individuals seeking natural alternatives to conventional medications for anxiety and sleep disorders.

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

InChI:InChI=1/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3/t12-/m0/s1

Upstream product

• 500-64-1 kawain 
• 104-53-0 3-phenyl-propionaldehyde 
• 90857-62-8 Brassard's diene 
• 592533-53-4 C₁₃H₁₄O₃ 
• 77-78-1 dimethyl sulfate 
• 125639-64-7 (S)-ethyl 2-hydroxy-4-phenylbutyrate 
• 115016-95-0 (S)-2-hydroxy-4-phenylbutanoic acid 
• 146912-63-2 (S)-2-hydroxy-4-oxo-4-phenylbutanoic acid 
• 67-56-1 methanol 
• 913258-21-6 (4S)-4-(2-phenylethyl)-1,3,2-dioxathiolane 2-oxide 
• 1443322-44-8 methyl 3-[(2S)-2-hydroxy-4-phenylbutyl]but-3-enoate 
• 100-39-0 benzyl bromide 
• 157732-87-1 (4S)-2,2-dimethyl-4-(2-phenylethyl)-1,3-dioxolane 
• 118629-73-5 (S)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate 

Downstream Products

• 845533-34-8 (8S)-hydroxy-(6S)-dihydrokawain 

Relevant articles and documents

Asymmetric synthesis of (S)-dihydrokavain from l-malic acid

A practical and efficient asymmetric synthesis of (S)-dihydrokavain from known ethyl (S)-2-hydroxy-4-phenylbutanoate which is, in turn, readily available from l-malic acid as a cheap chiral pool material is described using regioselective ring-opening of the 1,2-cyclic sulfate with lithium-3,3,3-triethoxypropiolate and subsequent HgO/H2SO4-mediated lactonization as the key steps. Its opposite enantiomer (R)-dihydrokavain was also synthesized from d-malic acid using the same sequences of reactions for the purpose of optical purity determination.

Asymmetric synthesis of (S)-vigabatrin and (S)-dihydrokavain via cobalt catalyzed hydrolytic kinetic resolution of epoxides

A concise route to the asymmetric synthesis of (S)-vigabatrin and (S)-dihydrokavain has been described using Co-catalyzed hydrolytic kinetic resolution of racemic epoxides and regiospecific opening of terminal epoxides with dimethylsulfonium me

Chemoenzymatic synthesis of enantiomerically enriched kavalactones

Lipase-mediated kinetic resolution of methyl-3-hydroxy-5-phenylpentanoate and (6E)-ethyl 5-hydroxy-3-oxo-7-phenylhept-6-enoate is described in high enantiomeric excess and good yields. The effect of different lipases in different solvents has been screened using different acylating agents. This protocol has been extended for the preparation of enantiomerically pure biologically important kavalactones.