495-85-2

Usage

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

• 5876-51-7 5-iodo-1,3-benzodioxole 
• 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 
• 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 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.

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.

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.

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.

Versatile asymmetric synthesis of the kavalactones: First synthesis of (+)-kavain

(Equation Presented) Three asymmetric pathways to the kavalactones have been developed. The first method is chiral auxiliary-based and utilizes aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/decarboxylation reaction. The second approach uses the asymmetric catalytic Mukaiyama additions of dienolate nucleophile equivalents developed by Carreira and Sato. Finally, tin-substituted intermediates, prepared by either of these routes, can serve as advanced general precursors of kavalactone derivatives via Pd(0)-catalyzed Stille couplings with aryl halides.

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.