Valproic Acid → (-)-Carnitine

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Reaction Steps

The inventors have discovered that simple admixture or combination of L-carnitine, a calcium or magnesium salt, and valproic acid without a suitable solvent is not sufficient to provide an L-carnitine valproate salt of the present invention. After simple admixture or combination without a suitable solvent, L-carnitine retains its objectionable malodor and offensive taste, as well as its hygroscopicity, and valproic acid remains an oil. In contrast, use of the methods of preparing the L-carnitine valproate salt of the present invention as disclosed herein provides a composition of the present invention that is free from objectionable taste and free or nearly free from repugnant odor. Further, an L-carnitine valproate salt of the present invention has different physico-chemical properties from the starting materials. As we discovered and disclose in Example 1, for example, L-carnitine calcium valproate, an embodiment of the present invention, has a melting point of 171.2° C., different from the melting point of L-carnitine (186-190° C.) or valproic acid (an oil at room temperature and above). The 1H-NMR spectrum of L-carnitine calcium valproate (FIG. 2) differs from that of the starting materials (i.e., L-carnitine and valproic acid) and confirms the structure. L-carnitine calcium valproate is soluble in water, and aqueous solutions of this salt provide bioavailable L-carnitine, calcium, and valproate.

Provenance & Evidence