495-85-2

Basic information

• Product Name: METHYSTICIN
• Synonyms: METHYLSTICIN;(6R)-6-[(E)-2-(1,3-Benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one;(+)-Methysticin;(R)-6-[(E)-2-(1,3-Benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one;d-Methysticin;R-(+)-Methysticin;NF-κB Activation Inhibitor X, Methysticin;(r-(e))-6-(2-(1,3-benzodioxol-5-yl)ethenyl)-5,6-dihydro-4-methoxy-2h-pyran-2
• CAS NO: 495-85-2
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27
• Product Categories: Coumarins;Aromatics;Chiral Reagents;Heterocycles;Mutagenesis Research Chemicals
• Mol File: 495-85-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 132-134°
• Boiling Point: 337.26°C (rough estimate)
• Flash Point: 224 °C
• Appearance: white powder
• Density: 1.1827 (rough estimate)
• Vapor Pressure: 5.39E-10mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 2-8°C
• BRN: 91701
• CAS DataBase Reference: METHYSTICIN(CAS DataBase Reference)
• NIST Chemistry Reference: METHYSTICIN(495-85-2)
• EPA Substance Registry System: METHYSTICIN(495-85-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 495-85-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 495-85-2 differently. You can refer to the following data:
1. A lactone isolated from the Kava plant (Piper methysticum).
2. A lactone isolated from the Kava plant (Piper methysticum). The active constituents of Kava are a group of approx. 18 compounds collectively referred to as kavalactones or kava pyrones. One of the active components of the intoxicating beverage Kava from the Pacific Islands.

InChI:InChI=1/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3

Upstream product

• 821775-38-6 3-(3′,4′-methylenedioxophenyl)propenal 
• 77-78-1 dimethyl sulfate 
• 58095-77-5 (E)-3,4-methylenedioxycinnamaldehyde 
• 120-57-0 piperonal 
• 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 
• 1682-37-7 3,4-(methylenedioxy)benzenediazonium tetrafluoroborate 
• 5876-51-7 5-iodo-1,3-benzodioxole 
• 26536-93-6 methyl 4-bromo-3-methoxy-2-butenoate 

Downstream Products

• 3155-57-5 (+/-)-dihydromethysticin 
• 19902-91-1 (+)-dihydromethysticin 
• 3384-27-8 7-benzo[1,3]dioxol-5-yl-3-methoxy-hepta-2,4-dienoic acid 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 120-57-0 piperonal 

Relevant articles and documents

Pilot in Vivo Structure-Activity Relationship of Dihydromethysticin in Blocking 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone-Induced O6-Methylguanine and Lung Tumor in A/J Mice

(+)-Dihydromethysticin was recently identified as a promising lung cancer chemopreventive agent, while (+)-dihydrokavain was completely ineffective. A pilot in vivo structure-activity relationship (SAR) was explored, evaluating the efficacy of its analogs in blocking 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced short-term O6-methylguanine and long-term adenoma formation in the lung tissues in A/J mice. Both results revealed cohesive SARs, demonstrating that the methylenedioxy functional group in DHM is essential while the lactone functional group tolerates modifications.

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.

Towards synthesis of kavalactone derivatives

Kavalactone derivatives were synthesized using a Heck reaction of the 4-methoxy-6-vinyl-5,6-dihydropyran-2-one with aryl iodides. The Suzuki-Miyaura reaction of an aryl boronic acid and (Z)-4-methoxy-6-(2-iodovinyl)-5,6-dihydropyran-2-one has also been successfully used to produce both Z and E isomers of lactones.