19902-91-1

Usage

Uses

Used in Pharmaceutical Industry:
Dihydromethysticin is used as an efflux transporter inhibitor for enhancing the uptake of P-glycoprotein (P-gp) substrates in cancer cells. It increases the 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.
Used in Pain Management:
Dihydromethysticin is used as an analgesic agent for pain relief. It has demonstrated analgesic activity by increasing the latency to tail withdrawal in the tail-flick assay in mice when administered at a dose of 275 mg/kg.
Used in Neuroprotection:
Dihydromethysticin is used as a neuroprotective agent for reducing 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.
Used in Toxicity Studies:
Dihydromethysticin is used in toxicity studies through in vitro analysis, as it is found in the roots of the kava plant and has potential applications in understanding its effects on human health and safety.

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 
• 495-85-2 (+)-methysticin 
• 495-85-2 (+/-)-methysticin 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 67-64-1 acetone 
• 674-82-8 4-methyleneoxetan-2-one 
• 30830-55-8 3-(3,4-methylenedioxyphenyl)propionaldehyde 
• 149-73-5 trimethyl orthoformate 
• 1092383-57-7 4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one 
• 117081-50-2 5,6-dihydro-6-ethenyl-4-hydroxy-2H-pyran-2-one 
• 77-78-1 dimethyl sulfate 
• 821775-38-6 3-(3′,4′-methylenedioxophenyl)propenal 
• 120-57-0 piperonal 

Downstream Products

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

Relevant academic research and scientific papers

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.

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.

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.

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.

Methods of using kavalactone compositions

This invention relates to methods of using compositions having health enhancing qualities, and more particularly to compositions having kavalactones, as well as use and preparation of the compositions.

Wood preservative

A wood preservative that comprises as an active ingredient a Piper methysticum, plant or a processed product thereof or a compound represented by Formula (I): wherein R1, R2, R3, R4 and R16 are same or different and each denotes a hydrogen atom, hydroxy or a C1-4 alkoxy, or R1 and R2 are taken together to form a group represented by —O—(CH2)n—O— wherein n is an integer of 1 to 3, R5 is a C1-4 alkoxy and X is —CH=CH—, —CH2—CH2— or epoxyethylene, and the bond: denotes a single bond or a double bond can prevent the attacking wood by an insect harmful to the wood and also prevents the appearance and the growth of a wood-rotting fungus or a wood- staining fungus while being highly safe to humans and animals without exerting no adverse effect on the environment.

Methods of using kavalactone compositions

This invention relates to methods of using compositions having health enhancing qualities, and more particularly to compositions having kavalactones, as well as use and preparation of the compositions.

Kavalactone compositions

This invention relates to compositions having health enhancing qualities, and more particularly to compositions having kavalactones, as well as use and preparation of the compositions.

Heterogeneous enantioselective hydrogenation of 2-pyrones over cinchona-modified palladium

Asymmetric hydrogenation of 4-alkoxy and 4-methyl derivatives of 2-pyrones to the corresponding dihydro- or tetrahydropyrones over cinchona-modified Pd/TiO2 is fast under ambient conditions and affords good yields and high ee. cis-Tetrahydropyr