|
|
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result sql = HPLC and LC-MS studies of the transesterification reaction of methylparaben with twelve 3- to 6-carbon sugar alcohols and propylene glycol and the isomerization of the reaction products by acyl migration.
HPLC and LC-MS studies of the transesterification reaction of methylparaben with twelve 3- to 6-carbon sugar alcohols and propylene glycol and the isomerization of the reaction products by acyl migration.char = S;code = 83
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char = ;code = 32
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result sql = Sugar alcohols and parabens are commonly used ingredients in oral suspension formulations. However, their possible incompatibility because of transesterification reaction is a concern during formulation development. In order to gain more knowledge about the reaction, a high-performance liquid chromatographic (HPLC) method is developed to separate the transesterification reaction products of methylparaben preservative with twelve 3- to 6-carbon sugar alcohols and propylene glycol. It is found that the number of peaks separated or partially separated correlate well with the number of distinct hydroxyl groups present in the sugar alcohol molecules. This means that all the hydroxyl groups in a sugar alcohol molecule can react with methylparaben to form transesterification reaction products. These products are positional isomers that have identical UV spectra with a maximum at 255 nm and the same m/z ratio for molecular ions by liquid chromatography-mass spectrometry. When isolated individually, they can isomerize (interconvert) under suitable conditions to form other positional isomers by intramolecular acyl migration. The acyl migration pathway for each of the isolated positional isomers from the transesterification reaction of methylparaben with sorbitol, ribitol, and xylitol is followed by HPLC. Based on the information, a tentative assignment of the six isomer peaks generated from the transesterification reaction between methylparaben and sorbitol is proposed.
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char = c;code = 99
char = o;code = 111
char = h;code = 104
char = o;code = 111
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = p;code = 112
char = y;code = 121
char = l;code = 108
char = e;code = 101
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = g;code = 103
char = l;code = 108
char = y;code = 121
char = c;code = 99
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = s;code = 115
char = o;code = 111
char = m;code = 109
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = z;code = 122
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = d;code = 100
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = b;code = 98
char = y;code = 121
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = y;code = 121
char = l;code = 108
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = g;code = 103
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = .;code = 46
result sql = HPLC and LC-MS studies of the transesterification reaction of methylparaben with twelve 3- to 6-carbon sugar alcohols and propylene glycol and the isomerization of the reaction products by acyl migration.
char = u;code = 117
char = g;code = 103
char = a;code = 97
char = r;code = 114
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = c;code = 99
char = o;code = 111
char = h;code = 104
char = o;code = 111
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = p;code = 112
char = a;code = 97
char = r;code = 114
char = a;code = 97
char = b;code = 98
char = e;code = 101
char = n;code = 110
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = m;code = 109
char = o;code = 111
char = n;code = 110
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = u;code = 117
char = s;code = 115
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = r;code = 114
char = e;code = 101
char = d;code = 100
char = i;code = 105
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = o;code = 111
char = r;code = 114
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = s;code = 115
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = s;code = 115
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = m;code = 109
char = u;code = 117
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = s;code = 115
char = .;code = 46
char = ;code = 32
char = H;code = 72
char = o;code = 111
char = w;code = 119
char = e;code = 101
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = ,;code = 44
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = i;code = 105
char = r;code = 114
char = ;code = 32
char = p;code = 112
char = o;code = 111
char = s;code = 115
char = s;code = 115
char = i;code = 105
char = b;code = 98
char = l;code = 108
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = b;code = 98
char = i;code = 105
char = l;code = 108
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = b;code = 98
char = e;code = 101
char = c;code = 99
char = a;code = 97
char = u;code = 117
char = s;code = 115
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = n;code = 110
char = s;code = 115
char = e;code = 101
char = s;code = 115
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = f;code = 102
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = i;code = 105
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = r;code = 114
char = n;code = 110
char = ;code = 32
char = d;code = 100
char = u;code = 117
char = r;code = 114
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = m;code = 109
char = u;code = 117
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = v;code = 118
char = e;code = 101
char = l;code = 108
char = o;code = 111
char = p;code = 112
char = m;code = 109
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = .;code = 46
char = ;code = 32
char = I;code = 73
char = n;code = 110
char = ;code = 32
char = o;code = 111
char = r;code = 114
char = d;code = 100
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = g;code = 103
char = a;code = 97
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = m;code = 109
char = o;code = 111
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = k;code = 107
char = n;code = 110
char = o;code = 111
char = w;code = 119
char = l;code = 108
char = e;code = 101
char = d;code = 100
char = g;code = 103
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = b;code = 98
char = o;code = 111
char = u;code = 117
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = h;code = 104
char = i;code = 105
char = g;code = 103
char = h;code = 104
char = -;code = 45
char = p;code = 112
char = e;code = 101
char = r;code = 114
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = m;code = 109
char = a;code = 97
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = ;code = 32
char = l;code = 108
char = i;code = 105
char = q;code = 113
char = u;code = 117
char = i;code = 105
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = h;code = 104
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = a;code = 97
char = t;code = 116
char = o;code = 111
char = g;code = 103
char = r;code = 114
char = a;code = 97
char = p;code = 112
char = h;code = 104
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = (;code = 40
char = H;code = 72
char = P;code = 80
char = L;code = 76
char = C;code = 67
char = );code = 41
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = d;code = 100
char = ;code = 32
char = i;code = 105
char = s;code = 115
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = v;code = 118
char = e;code = 101
char = l;code = 108
char = o;code = 111
char = p;code = 112
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = s;code = 115
char = e;code = 101
char = p;code = 112
char = a;code = 97
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = n;code = 110
char = s;code = 115
char = e;code = 101
char = s;code = 115
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = f;code = 102
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = d;code = 100
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = p;code = 112
char = a;code = 97
char = r;code = 114
char = a;code = 97
char = b;code = 98
char = e;code = 101
char = n;code = 110
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = e;code = 101
char = r;code = 114
char = v;code = 118
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = t;code = 116
char = w;code = 119
char = e;code = 101
char = l;code = 108
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = 3;code = 51
char = -;code = 45
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = 6;code = 54
char = -;code = 45
char = c;code = 99
char = a;code = 97
char = r;code = 114
char = b;code = 98
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = g;code = 103
char = a;code = 97
char = r;code = 114
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = c;code = 99
char = o;code = 111
char = h;code = 104
char = o;code = 111
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = p;code = 112
char = y;code = 121
char = l;code = 108
char = e;code = 101
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = g;code = 103
char = l;code = 108
char = y;code = 121
char = c;code = 99
char = o;code = 111
char = l;code = 108
char = .;code = 46
char = ;code = 32
char = I;code = 73
char = t;code = 116
char = ;code = 32
char = i;code = 105
char = s;code = 115
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = n;code = 110
char = u;code = 117
char = m;code = 109
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char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
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char = e;code = 101
char = a;code = 97
char = k;code = 107
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char = s;code = 115
char = e;code = 101
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char = a;code = 97
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char = a;code = 97
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char = e;code = 101
char = d;code = 100
char = ;code = 32
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = p;code = 112
char = a;code = 97
char = r;code = 114
char = t;code = 116
char = i;code = 105
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = y;code = 121
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char = s;code = 115
char = e;code = 101
char = p;code = 112
char = a;code = 97
char = r;code = 114
char = a;code = 97
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char = ;code = 32
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char = r;code = 114
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char = l;code = 108
char = a;code = 97
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char = l;code = 108
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char = h;code = 104
char = ;code = 32
char = t;code = 116
char = h;code = 104
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char = ;code = 32
char = n;code = 110
char = u;code = 117
char = m;code = 109
char = b;code = 98
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = s;code = 115
char = t;code = 116
char = i;code = 105
char = n;code = 110
char = c;code = 99
char = t;code = 116
char = ;code = 32
char = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = l;code = 108
char = ;code = 32
char = g;code = 103
char = r;code = 114
char = o;code = 111
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char = p;code = 112
char = r;code = 114
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char = s;code = 115
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char = t;code = 116
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char = i;code = 105
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char = e;code = 101
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char = u;code = 117
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char = a;code = 97
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char = o;code = 111
char = l;code = 108
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char = m;code = 109
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char = e;code = 101
char = c;code = 99
char = u;code = 117
char = l;code = 108
char = e;code = 101
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char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = i;code = 105
char = s;code = 115
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char = m;code = 109
char = e;code = 101
char = a;code = 97
char = n;code = 110
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char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
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char = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
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char = y;code = 121
char = l;code = 108
char = ;code = 32
char = g;code = 103
char = r;code = 114
char = o;code = 111
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char = p;code = 112
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char = i;code = 105
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char = ;code = 32
char = a;code = 97
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char = s;code = 115
char = u;code = 117
char = g;code = 103
char = a;code = 97
char = r;code = 114
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = c;code = 99
char = o;code = 111
char = h;code = 104
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = m;code = 109
char = o;code = 111
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = u;code = 117
char = l;code = 108
char = e;code = 101
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char = c;code = 99
char = a;code = 97
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char = r;code = 114
char = e;code = 101
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = ;code = 32
char = w;code = 119
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char = t;code = 116
char = h;code = 104
char = ;code = 32
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char = a;code = 97
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char = t;code = 116
char = i;code = 105
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char = p;code = 112
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char = u;code = 117
char = c;code = 99
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char = s;code = 115
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = s;code = 115
char = e;code = 101
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char = e;code = 101
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char = i;code = 105
char = o;code = 111
char = n;code = 110
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char = p;code = 112
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char = s;code = 115
char = e;code = 101
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result sql = Sugar alcohols and parabens are commonly used ingredients in oral suspension formulations. However, their possible incompatibility because of transesterification reaction is a concern during formulation development. In order to gain more knowledge about the reaction, a high-performance liquid chromatographic (HPLC) method is developed to separate the transesterification reaction products of methylparaben preservative with twelve 3- to 6-carbon sugar alcohols and propylene glycol. It is found that the number of peaks separated or partially separated correlate well with the number of distinct hydroxyl groups present in the sugar alcohol molecules. This means that all the hydroxyl groups in a sugar alcohol molecule can react with methylparaben to form transesterification reaction products. These products are positional isomers that have identical UV spectra with a maximum at 255 nm and the same m/z ratio for molecular ions by liquid chromatography-mass spectrometry. When isolated individually, they can isomerize (interconvert) under suitable conditions to form other positional isomers by intramolecular acyl migration. The acyl migration pathway for each of the isolated positional isomers from the transesterification reaction of methylparaben with sorbitol, ribitol, and xylitol is followed by HPLC. Based on the information, a tentative assignment of the six isomer peaks generated from the transesterification reaction between methylparaben and sorbitol is proposed.
Publication: J Chromatogr Sci 2002 Mar ;40(3)::170-7.
Publication Date: 2002 Mar
Study Author(s): Ma, Minhui;DiLollo, Antonio;Mercuri, Robert;Lee, Tony;Bundang, Mark;Kwong, Elizabeth;
Institution: Pharmaceutical Research & Development, Merck Frosst Canada & Co., Kirkland, Quebec.
Shortcut link to this study:
Publication Date: 2002 Mar
Study Author(s): Ma, Minhui;DiLollo, Antonio;Mercuri, Robert;Lee, Tony;Bundang, Mark;Kwong, Elizabeth;
Institution: Pharmaceutical Research & Development, Merck Frosst Canada & Co., Kirkland, Quebec.
Shortcut link to this study:
Sugar alcohols and parabens are commonly used ingredients in oral suspension formulations. However, their possible incompatibility because of transesterification reaction is a concern during formulation development. In order to gain more knowledge about the reaction, a high-performance liquid chromatographic (HPLC) method is developed to separate the transesterification reaction products of methylparaben preservative with twelve 3- to 6-carbon sugar alcohols and propylene glycol. It is found that the number of peaks separated or partially separated correlate well with the number of distinct hydroxyl groups present in the sugar alcohol molecules. This means that all the hydroxyl groups in a sugar alcohol molecule can react with methylparaben to form transesterification reaction products. These products are positional isomers that have identical UV spectra with a maximum at 255 nm and the same m/z ratio for molecular ions by liquid chromatography-mass spectrometry. When isolated individually, they can isomerize (interconvert) under suitable conditions to form other positional isomers by intramolecular acyl migration. The acyl migration pathway for each of the isolated positional isomers from the transesterification reaction of methylparaben with sorbitol, ribitol, and xylitol is followed by HPLC. Based on the information, a tentative assignment of the six isomer peaks generated from the transesterification reaction between methylparaben and sorbitol is proposed.
PMID: 11954655
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