Research On The Synthesis Of Coenzyme Q10, Ubiquinone

Coenzyme Q10, Ubiquinone(CoQ10) is a compound used as medicine and health-care product. As one of the most effective anti-oxidation product, Coenzyme Q10 is widely uesd in the cure of cardiovascular disease, hepatitis, cancer etc and in the improvement of immunotherapy. By now, there are only several countries that have the capability to produce in scale like Japan. In the paper, the auther did some research on synthesis Q10.There are three parts in the synthesis of Q10 The first part is the syntheis of matrix, that is (2E)-1 -(3-methyl-4-phenylsulfonylbut-2-enyl)-6-methyl-2,3,4-trimethoxylbenzene. 3,4,5-trimethoxytoluene was brominated to give 2-bromo-3,4,5-trimethoxytoluene, then reacted with Mg, followed by reaction with (E)-4-halogeno-2-methyl-phenylsulfonyl-2-butene to give compound (2E)-1-(3-methyl-4-phenylsulfonylbut-2-enyl)-6-methyl-2,3,4-trimethoxylbenzene. The yield is 90.4%. As a new compound, it was used as an intermediate of coenzyme Q10. (E)-4-halogeno-2-methyl-phenylsulfonyl-2-butene is synthesized by isoprene addition with phenylsulfonyl bromide, the yield is improved from 40% to 88.2% by comparison with original literature. We find a region isomer in this reaction, and then we research the machnism of this reaction.The second part is the synthesis of solanesyl bromide. It is obtained by bromide sonanesol with PBr3, The yield is 90.7%.The third part is cross-coupling reaction. Coupling reaction of the matrix and solanesyl bromide and then reductive elimination of the sulfone group by sodium-ethyl alcohol, and followed by CAN oxidation afforded CoQ10.The paper found a low- cost routine to synthesize Q10. Based on it, we changed the original material to 2,3,4,5-tetramethoxyltoluene in the hope of improving the rate of the last oxidation.