131135-40-5

Upstream product

• 478703-09-2 C₁₀H₁₁⁽²⁾H₃O₃ 
• 478703-05-8 5-hydroxy(²H₂)methyl-1,2,3-trimethoxybenzene 
• 478703-06-9 C₁₀H₁₁⁽²⁾H₂BrO₃ 
• 118-41-2 Eudesmic acid 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 

Downstream Products

• 478703-13-8 C₉H₉⁽²⁾H₃O₄ 
• 105801-92-1 2-((all-E)-1,1-dideuterio-3,7,11,15,19,23,27,31,35,39-decamethyl-tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl)-5,6-dimethoxy-3-trideuteriomethyl-[1,4]benzoquinone 

Relevant academic research and scientific papers

Synthesis of deuterium-labelled coenzyme Q10

Deuterium-labelled coenzyme Q10 ([2-CD3-1′-CD2]coenzyme Q10, coenzyme Q10-d5) was synthesized by condensation of 2,3-dimethoxy-[5-CD3]methyl-1, 4-hydroquinone with [1-CD2]decaprenol. Five positions were selected for deuteration as replacement at these positions allowed examination of every step of the synthesis. This examination was carried out by a combination of 1H- and 13C-nuclear magnetic spectrometry and mass spectrometry. Further, these positions have been proved to be metabolically stable. This reagent makes simultaneous quantification of the source of coenzyme Q10 (exogenously supplied or endogenously supplied) possible in biological samples by measurements on gas chromatography-mass spectrometry. Copyright

Synthesis of [3-D3]-, [3-13C]-, and [1,2-13C2]propynes and their use for the synthesis of [5-D3-methyl]-, [5-13C-methyl]-, and [5,6- 13,C2-2,5-cyclohexadienyl]ubiquinones 3

Three selectively labeled propynes were prepared either with deuterium or carbon-13 at position 3 and doubly labeled with carbon-13 at positions 1 and 2 by an alkylation reaction from the corresponding labeled or unlabeled monolithio acetylides and dimethylsulfates. Their lithiation with nBuLi gave the corresponding propynyllithium derivatives which reacted with dimethyl squarate to afford the corresponding propargylic alcohols. These were thermolysed in p-xylene to furnish [5-D3-methyl]-, [5-13C-methyl]-, and [5,6-13C2-2,5-cyclohexadienyl]ubiquinone. The farnesyl side chain was introduced onto the labeled quinones with farnesyl trimethyltin under BF3 catalysis to provide [5-D3-methyl]-, [5-13C-methyl]-, and [5,6-13C2- 2,5-cyclohexadienyl]ubiquinone 3 (6c, 6b, 6a, respectively).