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Usage

Uses

Used in Pharmaceutical Industry:
Ardisianone A is used as a therapeutic agent for its anti-inflammatory properties, helping to reduce inflammation and alleviate symptoms associated with various inflammatory conditions.
Used in Oncology:
Ardisianone A is utilized as an anti-cancer agent, targeting various types of cancer cells and potentially contributing to cancer treatment strategies. Its mechanism of action may involve the modulation of cellular processes that promote tumor growth and progression.
Used in Microbiology:
Ardisianone A serves as an anti-microbial agent, exhibiting activity against certain microorganisms, which could be beneficial in the development of new antimicrobial drugs to combat resistant strains.
Used in Malaria Treatment Research:
Ardisianone A is employed as a potential treatment for malaria, with ongoing studies investigating its efficacy and mechanism in combating the Plasmodium parasites responsible for this disease.

InChI:InChI=1/C22H34O3/c1-4-5-9-13-19(21-17-20(23)15-16-22(21)24)14-11-8-6-7-10-12-18(2)25-3/h6,8,15-19H,4-5,7,9-14H2,1-3H3/b8-6+

Upstream product

• 34809-61-5 1,3-dimethoxy-5-<(Z)-10'-pentadecenyl>benzene 
• 148808-17-7 1,3-dimethoxy-5-<10-(2-tetrahydropyranyloxy)decanyl>benzene 
• 148808-16-6 1,3-dimethoxy-5-<10-(2-tetrahydropyranyloxy)-1-decenyl>benzene 
• 152430-95-0 10-(3,5-Dimethoxy-phenyl)-decan-1-ol 
• 137786-97-1 10-(3,5-dimethoxyphenyl)decanal 
• 13019-22-2 9-Decen-1-ol 
• 70863-80-8 9-((tetrahydro-2H-pyran-2-yl)oxy)nonan-1-al 
• 67136-13-4 1-(tetrahydro-2-pyranyloxy)-9-decene 
• 137786-94-8 belamcandol B 

Downstream Products

• 137786-93-7 belamcandaphenol 
• 148808-21-3 1,4-dihydroxy-2-methoxy-6-<(Z)-10'-pentadecenyl>benzene 

Relevant academic research and scientific papers

Ultrasound-assisted Wittig reaction: A short, efficient synthesis of 2-methoxy-6-alkyl-1,4-benzoquinones

A short, efficient synthesis of 2-methoxy-6-alkyl-1,4-benzoquinones is described. Ultrasound-assisted Wittig reaction of alkyltriphenyl phosphonium bromides with o-vanillin in basic aqueous conditions followed by reduction with Na/n-BuOH gave 2-methoxy-6-alkylphenols. Oxidation of 2-methoxy-6-alkylphenols with Fremy's salt produced the title compounds.

Synthesis of Natural Compounds with Alkyl-methoxy-1,4-benzoquinone Structure

The 1,4-benzoquinones 1-7 occurring in various plants and having interesting biological properties have been synthesized from the tetrahydropyranyl ethers 17 and 21.Reaction with n-butyllithium gave selectively the ortho-lithiated compounds.These could be alkylated with the haloalkenes 13-16 and haloalkanes to give the substituted phenols 18-20 and 22-25 in high yield after methanolysis.Alkylations of the methoxyisopropylether 8 of 10-undecyn-1-ol with bromobutane and bromohexane gave 9 and 10.These alkynols could be selectively hydrogenated with Lindlar-Palladium catalyst to give the (Z)-alkenols 11 and 12 which could be converted into the bromoalkenes 13, 14 and the iodoalkenes 15, 16.Oxidation of the phenols 18-20 and 22-25 with molecular oxygen in the presence of salcomine as catalyst produced the substituted 1,4-benzoquinones 1-3 and 26-29 in high yield.Selective hydrolysis with perchloric acid converted 26-29 into the natural products 4-7. - Key Words: Tetrahydropyranyl-ethers / ortho-Lithiation / ortho-Alkylation / 1,4-Benzoquinones, alkyl-methoxy- / 1,4-Benzoquinones, alkyl-hydroxy-methoxy-

Naturally occurring 5-lipoxygenase inhibitor. II. Structures and syntheses of ardisianones A and B, and maesanin, alkenyl-1,4-benzoquinones from the rhizome of Ardisia japonica

New alkenyl-1,4-benzoquinones, ardisianones A (1) and B (2), and the known maesanin (3) as 5-lipoxygenase inhibitors have been isolated from the rhizome of Ardisia japonica. Their structures have been elucidated as 2-methoxy-6-[(Z)-10'-pentadecenyl]-1,4-benzoquinone and 5-hydroxy-2-methoxy-6-[(Z)-8'-tridecenyl]-1,4-benzoquinone, respectively, on the basis of spectroscopic data and chemical degradation. Ardisianone A (1), maesanin (3) and belamcandol A (7) have been synthesized starting from belamcandol B (6), readily prepared by Wittig reaction between 9-(2-tetrahydropyranyloxy)nonanal and 3,5-dimethoxybenzyltriphenylphosphonium bromide followed by selective demethylation with sodium thioethoxide.