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

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

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

• 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 
• 104-53-0 3-phenyl-propionaldehyde 
• 592533-53-4 C₁₃H₁₄O₃ 
• 77-78-1 dimethyl sulfate 
• 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 
• 125103-96-0 (S)-5-phenyl-3-hydroxypentanenitrile 
• 124988-64-3 (S)-4-phenyl-1,2-butanediol 
• 1449-46-3 benzyltriphenylphosphonium bromide 

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.

Efficient enantioselective hetero-diels-alder reaction of brassard's diene with aliphatic aldehydes: A one-step synthesis of (R)-(+)-kavain and (S)-(+)-dihydrokavain

An efficient catalytic asymmetric hetero-Diels-Alder reaction of Brassard's diene with aliphatic aldehydes was reported The catalyst which was generated from (R)-BINOL, Ti(i-PrO)4, and 4-picolyl chloride hydrochloride, promoted the reaction smoothly to afford the corresponding α, β-unsaturated λ-lactone derivatives in moderate-to-good yields (46-79%) with high enantioselectivities (up to 88% ee) Natural products (R)-(+)-kavain (70% ee, > 99% ee after single re crystallization) and (S)-(+)-dihydrokavain (84% ee) were also prepared in one step by using this methodology.

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.