3155-57-5

Basic information

• Product Name: DIHYDROMETHYSTICIN
• Synonyms: DIHYDROMETHYSTICIN;NSC23878;6-[2-(1,3-Benzodioxol-5-yl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one;2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
• CAS NO: 3155-57-5
• Molecular Formula: C15H16O5
• Molecular Weight: 276.28
• Mol File: 3155-57-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 118°
• Boiling Point: 476.1 ºC at 760 mmHg
• Flash Point: 214.1 ºC
• Appearance: /
• Density: 1.28 g/cm³
• CAS DataBase Reference: DIHYDROMETHYSTICIN(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDROMETHYSTICIN(3155-57-5)
• EPA Substance Registry System: DIHYDROMETHYSTICIN(3155-57-5)

Safety Data

• Hazardous Substances Data: 3155-57-5(Hazardous Substances Data)

Usage

General Description

Dihydromethysticin is a chemical compound found in the kava plant, traditionally used in the Pacific Islands for its sedative and anxiolytic properties. It belongs to the class of compounds known as kavalactones, which are believed to be responsible for the plant's psychoactive effects. Dihydromethysticin has been shown to have potential as a natural remedy for anxiety and stress, with some studies suggesting that it may help to reduce symptoms of anxiety without causing the sedative effects associated with other kavalactones. It is also being explored for its potential as a treatment for cancer, due to its ability to induce cell death in certain cancer cell lines. However, further research is needed to fully understand the potential benefits and risks of dihydromethysticin.

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 30830-55-8 3-(3,4-methylenedioxyphenyl)propionaldehyde 
• 149-73-5 trimethyl orthoformate 
• 77-78-1 dimethyl sulfate 
• 821775-38-6 3-(3′,4′-methylenedioxophenyl)propenal 
• 495-85-2 (+/-)-methysticin 
• 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 
• 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 
• 67-64-1 acetone 
• 64-17-5 ethanol 

Downstream Products

• 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.

Synthesis of β-methoxyacrylate natural products based on box-Pd IIcatalyzed intermolecular methoxycarbonylation of alkynoles

Bis(oxazoline)-palladium(II) catalyzed carbonylation of homopropargyl alcohols afforded acyclic methoxyacrylate 2 and 6-membered lactone 3a-k in good combined yield. In the case of propargyl alcohols, 5-membered lactones 3p, 3q, 16 were obtained in moderate yields. The one-pot synthesis of kawa lactones 3a, 3r, 3s and formal synthesis of dihydroxycystothiazole A and dihydroxycystothiazole C are presented. To elucidate the stereochemistry of (+)-annularin G and (-)-annularin H, the first asymmetric syntheses of these natural products were achieved.

Polymer-supported electron-rich diene for hetero Diels-Alder reactions

A Brassard diene analogue was grafted on a modified Merrifield resin and used in a hetero Diels-Alder reaction with various aldehydes or ketones. The reaction gave access to 6-substituted 5,6-dihydropyrones (5a-u). This new immobilized electron-rich diene is more stable than the corresponding native diene, and is a versatile supported reagent.