83036-57-1

Upstream product

• 60699-32-3 (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 918800-77-8 2,3,4,5-tetramethoxy-6-methylphenylmagnesium bromide 
• 35896-58-3 2,3,4,5-tetramethoxytoluene 
• 83036-59-3 geranyl diisopropyl phosphate 
• 6138-90-5 trans-geranyl bromide 
• 13909-73-4 2',3',4'-trimethoxyacetophenone 
• 65884-12-0 2,3,4,5-tetramethoxybenzaldehyde 
• 19676-64-3 2,3,4-trimethoxyphenol 
• 73875-27-1 2,3,4,5-tetramethoxy-6-methyl-1-bromobenzene 
• 106-24-1 Geraniol 
• 25245-39-0 1-bromo-2,3,4,5-tetramethoxybenzene 
• 21450-56-6 1,2,3,4-tetramethoxybenzene 
• 106-44-5 p-cresol 
• 203059-93-2 4a-((E)-3,7-Dimethyl-octa-2,6-dienyl)-6,7-dimethoxy-8a-methyl-1,4,4a,8a-tetrahydro-1,4-methano-naphthalene-5,8-dione 

Downstream Products

• 606-06-4 2-[(E)-3,7-dimethyl-2,6-octadienyl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone 
• 85228-79-1 1-<(2E)-6,7-epoxy-3,7-dimethyloct-2-enyl>-2,3,4,5-tetramethoxy-6-methylbenzene 
• 99347-84-9 1-((E)-6-Chloro-3,7-dimethyl-octa-2,7-dienyl)-2,3,4,5-tetramethoxy-6-methyl-benzene 
• 849034-07-7 3-bromo-2,6-dimethyl-8-(2-methyl-3,4,5,6-tetramethoxyphenyl)oct-6-en-2-ol 
• 4370-62-1 2-<(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl>-3-methyl-5,6-dimethoxy-1,4-benzoquinone 
• 85228-84-8 (E)-2,6-Dimethyl-8-(2,3,4,5-tetramethoxy-6-methyl-phenyl)-octa-1,6-dien-3-ol 
• 102745-41-5 1-<(2E,6E,10E)-3,7,11,15-tetramethyl-9-(p-tolylsulfonyl)hexadeca-2,6,10,15-tetraenyl>-2,3,4,5-tetramethoxy-6-methylbenzene 
• 102779-87-3 1-<(2E,6E,10E)-9-(methoxycarbonyl)-3,7,11,15-tetramethyl-9-(p-tolylsulfonyl)hexadeca-2,6,10,14-tetraenyl>-2,3,4,5-tetramethoxy-6-methylbenzene 
• 114094-40-5 C₇₈H₁₀₄O₁₇S₃ 
• 114060-26-3 1-<(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl>-6-methyl-2,3,4,5-tetramethoxybenzene 
• 114060-25-2 1-<(2E)-6-<(methoxycarbonyl)oxy>-3,7-dimethylocta-2,7-dienyl>-2,3,4,5-tetramethoxy-6-methylbenzene 
• 114060-36-5 (4E,8E)-2-((E)-5-Hydroxy-2,6-dimethyl-hepta-1,6-dienyl)-4,8-dimethyl-10-(2,3,4,5-tetramethoxy-6-methyl-phenyl)-2-(toluene-4-sulfonyl)-deca-4,8-dienoic acid methyl ester 
• 114060-27-4 1-<(2E,6E,10E)-9-(methoxycarbonyl)-14-<(methoxycarbonyl)oxy>-3,7,11,15-tetramethyl-9-(p-tolylsulfonyl)hexadeca-2,6,10,15-tetraenyl>-2,3,4,5-tetramethoxy-6-methylbenzene 
• 114060-37-6 (3E,7E)-2-[(2E,6E)-2,6-Dimethyl-8-(2,3,4,5-tetramethoxy-6-methyl-phenyl)-octa-2,6-dienyl]-10-((E)-5-hydroxy-2,6-dimethyl-hepta-1,6-dienyl)-4,8-dimethyl-2,10-bis-(toluene-4-sulfonyl)-undeca-3,7-dienedioic acid dimethyl ester 

Relevant academic research and scientific papers

Synthesis of natural product-like polyprenylated phenols and quinones: Evaluation of their neuroprotective activities

Twenty-seven natural product-like polyprenylated phenols and quinones were synthesized and their neuroprotective activity was tested using human monoamine oxidase B (MAO-B) and SH-SY5Y cells. Eight compounds inhibited MAO-B (IC50 values 25 μM

The preparation of side chain functionalized analogues of coenzyme Q for protein conjugation studies

The synthesis of two analogues of CoQ (10 and 13) suitable for conjugation to a peptide or protein, and hence the development of an ELISA immunoassay, is presented. These analogues were synthesized from the protected quinone, 1-bromo-2-methyl-3,4,5,6-tetramethoxybenzene (1), itself prepared from commercially available CoQ-0 (3). Model coupling studies of one of the analogues (10) to N-acetyl-L-lysine methyl ester and a lysine containing dipeptide (N-acetylglycine-L-lysine methyl ester) were also undertaken as a first step to monoclonial antibody production.

Synthesis of coenzyme Q10 ubiquinone

Processes for the stereospecific synthesis of coenzyme Q10, ubiquinone, are disclosed; a total synthetic procedure using geraniol as the starting material. The process of the invention results in high yields of isometrically pure ubiquinone. The synthetic coenzyme Q10 can be used as an antioxidant, a nutritional supplement and as a pharmaceutical in treating many conditions.

Total Synthesis of Linear Polyprenoids. 2. Improved preparation of the Aromatic Nucleus of Ubiquinone

Highly efficient copper-catalyzed polymethoxylation of tribromocresol is the key process in a three-step, practical approach to obtain ubiquinone 0 from p-cresol.Short syntheses of several ubiquinones were achieved via direct, copper-mediated coupling of 2-lithio-3,4,5,6-tetramethoxytoluene to the appropriate polyprenyl bromide.

AN EFFICIENT REGIO- AND STEREOSPECIFIC ALKENYLATION OF PHENOLIC ETHERS BY PRENYL AND GERANYL DIISOPROPYL PHOSPHATES

Prenyl and geranyl diisopropyl phosphates readily alkenylate a variety of phenolic ethers regio- and stereospecifically without any appreciable side reactions.

Quinones. Part 2. General Synthetic Routes to Quinone Derivatives with Modified Polyprenyl Side Chains and the Inhibitory Effects of these Quinones on the Generation of the Slow Reacting Substance of Anaphylaxis (SRS-A)

General synthetic routes to quinone acids (8), quinone amides (9), quinone alcohols (10), and quinone methylketones (11) with polyprenyl side chains, in which allylic alcohols (3) are employed as the key intermediates, are described.The Claisen rearrangements and the Carrol reactions of the allylic alcohols (3) with ethyl orthoacetate and diketen produced the ethyl esters (4) and the methylketones (5), respectively.Quinone products (8), (10), and (11) were recovered by oxidative demethylation of hydroquinone dimethyl ethers (4), (5), and (7) or by acid hydrolysis of hydroquinone bis(methoxymethyl) ethers (4) and (5) followed by ferric chloride oxidation.Amidation of quinone acids (8) led to the formation of quinone amides (9).Inhibitory effects of these quinone derivatives on the generation of the slow reacting substance of anaphylaxis (SRS-A) in the lungs of sensitised guinea pigs are evaluated.

SYNTHESIS OF UBIQUINONE AND MENAQUINONE ANALOGUES BY OXIDATIVE DEMETHYLATION OF ALKENYLHYDROQUINONE ETHERS WITH ARGENTIC OXIDE OR CERIC AMMONIUM NITRATE IN THE PRESENCE OF 2,4,6-PYRIDINE-TRICARBOXYLIC ACID

It was found that alkenylhydroquinone ethers demethylated with argentic oxide or ceric ammonium nitrate in the presence of 2,4,6-pyridinetricarboxylic acid as a catalyst and afforded ubiquinone-2, menaquinone-2 and their analogs in yields of 53 to 89 percent.The new approach to the synthesis of starting alkenylhydroquinone ethers as well as 2,4,6-pyridinetricarboxylic acid and its derivatives has been reported.