The Lipshutz Method
The coenzyme Q10 (CoQ10) supplied worldwide is produced by two distinct processes: fermentation and synthesis. Most traditional synthetic approaches to coenzyme Q10 are based upon joining two key subsections, the “head” and the “tail”. Both subsections are isolated from natural sources. The ‘head’ portion is obtained from the tannins found in wood, while the ‘tail’ is modified from an ingredient, solanesol, derived from tobacco waste. Both processes can produce coenzyme Q10 that is of high quality.
There are several aspects to the Lipshutz route to coenzyme Q10, developed at the University of California, that distinguish it from other synthetic processes. Most importantly, with the Lipshutz method, the ‘tail’ is attached to the ‘head’ in the natural, or all ‘trans’ orientation. The resulting molecule is referred to as the trans isomer of coenzyme Q10.
Cis-trans isomers describe the orientation of functional groups within molecules that contain double bonds. When the groups are arranged on the same side of the double bond, the isomer is referred to as cis. When the groups are oriented on opposite sides, a trans isomer exists. An example of a hydrocarbon displaying cis-trans isomerism is the 4-carbon-containing compound, 2-butene, as illustrated below.
Since interconversion between cis and trans isomers does not readily occur, the isomers are completely different compounds and usually have different physical properties. The ‘cis’ isomer of coenzyme Q10 is an undesirable, non-natural side-product formed by other synthetic approaches and has no nutritional value.
Next in importance, the number of manipulations needed to arrive at natural coenzyme Q10 is minimized in the Lipshutz method. Reducing the extent of handling achieves lower costs of manufacturing, less utilization of energy-dependent resources, and a significant decrease in the amount of waste generated and potentially released into the environment. To accomplish all of these goals, the Lipshutz method, achieves the joining, or coupling, of the head and tail portions by chemically “stitching” the fragments together. This can be realized in a single vessel, and at the site in the newly formed coenzyme Q10 that determines side chain geometry, as indicated in the following image.
The result is all-natural coenzyme Q10, which contains a ‘hairpin-like’ orientation in space, as illustrated below.
This method is by far the “cleanest”, most direct route to coenzyme Q10. This innovative process takes advantage of small quantities of two trace metals that serve as catalysts (chemicals that increase the rate of a reaction without undergoing change themselves) to form the required carbon-carbon (C-C) bond. Thus, the Lipshutz technology provides access to potentially unlimited amounts of pure coenzyme Q10 using the minimum number of steps. It yields the natural, nutritionally relevant trans-isomer exclusively while placing very little stress on the environment.