Synthesis Of Coenzyme Q₁₀

Coenzyme Q₁₀ exists widely in the body of many animals including human and plants. It has the ability of transporting hydrogen in respiration system, and anti-oxidation. With the developments of researches on its applications, it is found that coenzyme Q₁₀ has good cure ability for cardiovascular diseases, such as heart-angina, arrhythmia and hypertension. Besides, i t c an a ssist t he c ure o f h epatitis, c ancer e tc and i s u seful i n t he i mprovement o f immunotherapy. As coenzyme Q₁₀ has the ability of anti-oxidation, it has also been used in health-care and cosmetics.Based on coenzyme Q₁₀'s wide applications, many researchers pay attention to the synthesis of it in different ways. A practical route of chemical synthesis of coenzyme Q₁₀ is developed in this paper.Benzenesulfonyl bromide is given from sodium benzenesulfinate and bromine in 98.1%, which reacts with isoprene to give 4-bromo-2-methyl-l-phenylsulfonyl-2-butene (compound 2) with the yield of 88.2%.The 2,3,4,5-tetramethoxytoluene as the starting material reacts with compound 2 to give (2E)-l-(3-methyl-4-phenylsulfonylbut-2-enyl)-6-methyl-2,3,4,5-tetramethoxylbenzene (compound 4), the yield is 75.0%, which is a key intermediate product in this route.Solanesyl bromide is got from the brominating reaction between solanesol and Vilsmeier reagent. Coupling reaction of solanesyl bromide with compound 4 in the presence of potassium tert-butoxide gives compound 5, which is another intermediate product, in 51.9%. Coenzyme Q₁₀ is obtained by eliminating phenylsulfonyl group of compound 5 and the following oxidation.The total yield of this routine is 15.5%, while the conditions are mild, so what we have done provides useful data for the industrial synthesis of coenzyme Q₁₀.