Valproic Acid → (-)-Carnitine

HRID 273254

Reaction equation

HRID 273254 reaction equation
[OH:1][C@H:2]([CH2:8][C:9](=[O:11])[O-:10])[CH2:3][N+:4]([CH3:7])([CH3:6])[CH3:5].[C:12]([OH:21])(=[O:20])[CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16].C([O-])(=O)C(CCC)CCC.[Ca+2:32].O[C@H](CC(=O)[O-])C[N+](C)(C)C.C([O-])(=O)C(CCC)CCC>O>[OH:1][C@H:2]([CH2:8][C:9](=[O:10])[O-:11])[CH2:3][N+:4]([CH3:7])([CH3:5])[CH3:6].[Ca:32].[C:12]([O-:21])(=[O:20])[CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 3

HCID 3121Valproic Acid3×HCID 10917(-)-Carnitine3×HCID 24936378L-carnitine calcium valproate3×

Product 3

HCID 10917(-)-CarnitineHCID 3549980ValproateHCID 5460341Calcium

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. customas disclosed herein provides a composition of the present invention that
  2. customat room temperature

Sources & evidence

ORD record
ord-9caebc7359e54cb1a270bf525cc2c29c
Source dataset
uspto-grants-2008_11
Patent number
US07456216B2

Linked notes

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