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

Description

METHYSTICIN, also known as kava pyrone or kavalactone, is a lactone compound isolated from the Kava plant (Piper methysticum). It is one of the active constituents of the intoxicating beverage Kava, which is traditionally consumed in the Pacific Islands. METHYSTICIN possesses various pharmacological properties and is considered a promising candidate for various applications.
Used in Pharmaceutical Industry:
METHYSTICIN is used as a therapeutic agent for its anxiolytic, sedative, and muscle relaxant properties. It is commonly used in the treatment of anxiety disorders, insomnia, and restlessness. METHYSTICIN is believed to modulate the activity of the gamma-aminobutyric acid (GABA) receptors, leading to its calming effects.
Used in Dietary Supplements:
METHYSTICIN is used as a dietary supplement to promote relaxation and reduce stress. It is often found in the form of capsules, tablets, or liquid extracts, which can be consumed to alleviate anxiety and stress-related symptoms.
Used in Traditional Medicine:
In the Pacific Islands, METHYSTICIN has been traditionally used as a key component of the Kava beverage, which is consumed during cultural and religious ceremonies. It is believed to induce a state of relaxation and well-being, promoting social harmony and fostering a sense of community.

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

• 26536-93-6 methyl 4-bromo-3-methoxy-2-butenoate 
• 58095-77-5 (E)-3,4-methylenedioxycinnamaldehyde 
• 1092383-57-7 4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one 
• 5876-51-7 5-iodo-1,3-benzodioxole 
• 1682-37-7 3,4-(methylenedioxy)benzenediazonium tetrafluoroborate 
• 117081-50-2 5,6-dihydro-6-ethenyl-4-hydroxy-2H-pyran-2-one 
• 120-57-0 piperonal 
• 77-78-1 dimethyl sulfate 
• 821775-38-6 3-(3′,4′-methylenedioxophenyl)propenal 

Downstream Products

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

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.

Economically viable efficient synthesis of (±)-methysticin: A component in kava potentially responsible for its cancer chemopreventive activity

A highly efficient and green synthesis of (±)-methysticin was developed from inexpensive piperonal, requiring two extraction procedures and one chromatographic purification in the final step with 51% overall yield. This new method is superior compared to known literature procedures and is highly reproducible and scalable up to gram scale. ARKAT-USA, Inc.

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.