19902-91-1

Basic information

• Product Name: DIHYDROMETHYSTICIN
• Synonyms: 6-(2-(1,3-benzodioxol-5-yl)ethyl)-5,6-dihydro-4-methoxy-2h-pyran-2-on(s);6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)phenethyl)-(s)-2h-pyran-2-on;7,8-dihydromethysticin;dhm;DIHYDROMETHYLSTICIN;7,8-DIHYDROMETHYLSTICIN;5,6-Dihydro-4-methoxy-6-[2-(1,3-benzodioxol-5-yl)ethyl]-2H-pyran-2-one;6-[2-(1,3-Benzodioxol-5-yl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
• CAS NO: 19902-91-1
• Molecular Formula: C15H16O5
• Molecular Weight: 276.28
• Product Categories: Coumarins
• Mol File: 19902-91-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 117-118 °C
• Boiling Point: 476.1 °C at 760 mmHg
• Flash Point: 214.1 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 3.13E-09mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly), Pyridine (Slightly)
• Stability: Hygroscopic
• BRN: 91699
• CAS DataBase Reference: DIHYDROMETHYSTICIN(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDROMETHYSTICIN(19902-91-1)
• EPA Substance Registry System: DIHYDROMETHYSTICIN(19902-91-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19902-91-1(Hazardous Substances Data)

Usage

Description

Dihydromethysticin is a kavalactone originally isolated from P. methysticum (kava-kava) that has diverse biological activities, including efflux transporter inhibitory, antinociceptive, and neuroprotective properties. Dihydromethysticin is a P-glycoprotein (P-gp) inhibitor that increases uptake of the P-gp substrate calcein AM by 50% in P388 mouse leukemia cancer cells overexpressing P-gp when used at a concentration of 54.6 μM. Dihydromethysticin (275 mg/kg) has analgesic activity, increasing the latency to tail withdrawal in the tail-flick assay in mice. It also decreases the infarct size in a mouse model of ischemia induced by microbipolar coagulation of the left middle cerebral artery (MCA) when administered at a dose of 10 mg/kg.

Uses

(6S)-6-[2-(1,3-Benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one, is used in toxicity studies through in vitro analysis. This complex is found in the roots of kava plant.

InChI:InChI=1/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3

Upstream product

• 3129-60-0 (E)-6-[2-(benzo[d][1,3]dioxol-5-yl)vinyl]-4-methoxy-2H-pyran-2-one 
• 120-57-0 piperonal 
• 495-85-2 (+/-)-methysticin 
• 821775-38-6 3-(3′,4′-methylenedioxophenyl)propenal 
• 77-78-1 dimethyl sulfate 
• 30830-55-8 3-(3,4-methylenedioxyphenyl)propionaldehyde 
• 117081-50-2 5,6-dihydro-6-ethenyl-4-hydroxy-2H-pyran-2-one 
• 1092383-57-7 4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 1257109-04-8 1-[benzo[d][1,3]dioxol-5-yl]hex-5-yn-3-ol 
• 674-82-8 4-methyleneoxetan-2-one 
• 149-73-5 trimethyl orthoformate 
• 67-64-1 acetone 

Downstream Products

• 3384-27-8 7-benzo[1,3]dioxol-5-yl-3-methoxy-hepta-2,4-dienoic acid 

Relevant articles and documents

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Heck-matsuda arylation as a strategy to access kavalactones isolated from polygala sabulosa, piper methysticum, and analogues

Herein, we describe the total syntheses of three bioactive pyrones isolated from Polygala sabulosa (i.e., 1, 4, and 7) and eight isolated from Piper methysticum (i.e., 8-10, 13, 15, and 18-20) using the Heck-Matsuda arylation as the key strategy. The evaluation of this methodology by employing different arenediazonium tetrafluoroborates revealed that the Heck arylation was more efficient when the olefin undergoing arylation possessed the vinyl-2-pyrone structural unit instead of the vinyl dihydro-2-pyrone moiety. The Heck-Matsuda arylation of many of the examined olefins proceeded in a practical manner with total regio- and stereocontrol.

Highly regio- and stereoselective Heck reaction of allylic esters with arenediazonium salts: Application to the synthesis of kavalactones

Image Presented A highly efficient palladium-catalyzed Heck reaction of allylic esters with arenediazonium salts is described. The reaction proceeds under mild conditions, with excellent to total regio- and stereochemical control and with retention of the traditional leaving group. Furthermore, the generality of the present methodology is illustrated by the short total synthesis of the natural kavalactones, yangonine, (±)-methysticin, and (±)-dihydromethysticin.