2,3-dihydroxypropyl octadecanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a twin shell blender were placed 369.6 grams of the dried wet granulation of Example 3, 369.6 grams glyceryl monostearate (Myvaplex® 600, Eastman Chemical Co.), 33.2 grams of aspartame (The NutraSweet Co.), 21.6 grams of apple cinnamon durarome #860.310/TD 05.91 (Firminich Inc.), and 27.6 grams of an artificial special compound flavor (Firminish Inc.). This mixture was blended for 10 minutes after which 138.6 grams of Pregelatinized Starch (Starch 1500 Colorcon), 969.8 grams of granular mannitol, and 27.6 grams of crosslinked sodium carboxymethylcellulose (Accelerate™, FMC Corporation) were added to the blender. Mixing was continued for 10 more minutes, and then 19.4 grams of magnesium stearate was added to the blender. Mixing was completed in five minutes. Prior to adding each material to the blender, it was passed through a Number 30 US Standard Sieve. This mixture was then compressed into a tablet. The particle size distribution of the granulation used in this formulation was determined by using a Sonic Sifter, a vibrated stack of U.S. Standard Sieves in which each succeeding sieve is finer in mesh than the one above it. The amount of product retained on each sieve provides the percentage of particles larger than that sieve, but smaller then the next higher sieve. Particles having sizes in each mesh range were: 48.23%>297 microns (>50 mesh); 29.657% 177-297 microns (50-80 mesh); 5.39% 149-177 microns (80-100 mesh); 13.57% 74-149 microns (100-200 mesh); 3.17% 53-74 microns (200-270 mesh); and 5.00%<53 microns (<270 mesh). The loose bulk density of this material was 0.6164 grams/mL. The water content of the granulation was 1.50%. Properties of the chewable tablets include tablet thickness (3.25 mm, 0.1279 inch), hardness (5.37 kiloponds), and disintegration time in 37° C. purified water (184 seconds). All of these measurements were taken on ten tablets except disintegration time which used six tablets. The unpleasant flavor of ibuprofen was effectively masked by using the wet granulation in combination with other excipients. Mixing Mixing was completed in five minutes Prior to adding each material to the blender, it provides the percentage of particles larger than that sieve in 37° C. purified water (184 seconds)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of glycerol (30 g, 326 mmol) and pyridine (25 ml) dissolved in DMF (300 ml) was added dropwise stearoyl chloride (10 g, 33 mmol) dissolved in DMF 100 ml9. The mixture was cooled on an ice bath until addition was complete, whereupon the reaction was maintained under an N2 atmosphere overnight. After 15 hours CH2CL2 (300 ml) and saturated NaHCO3 (aq) was added. The phases were separated and the organic phase washed with water (50 ml) and dried with Na2SO4. The solvent and any pyridine were evaporated under vacuum. The crude product was chromatographed on a silica column (CH2Cl2-MeOH, 20:1) and recrystallised (CH2Cl2-ether) to yield around 7 grams. The mixture was cooled on an ice bath until addition was maintained under an N2 atmosphere overnight The phases were separated the organic phase washed with water (50 ml) dried with Na2SO4 The solvent and any pyridine were evaporated under vacuum The crude product was chromatographed on a silica column (CH2Cl2-MeOH, 20:1) recrystallised (CH2Cl2-ether) to yield around 7 grams

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Octadecanoic acid, monoester with 1,2,3-propanetriol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of glycerol (30 g, 326 mmol) and pyridine (25 ml) dissolved in DMF (300 ml) was added dropwise stearoyl chloride (10 g, 33 mmol) dissolved in DMF 100 ml9. The mixture was cooled on an ice bath until addition was complete, whereupon the reaction was maintained under an N2 atmosphere overnight. After 15 hours CH2CL2 (300 ml) and saturated NaHCO3 (aq) was added. The phases were separated and the organic phase washed with water (50 ml) and dried with Na2SO4. The mixture was cooled on an ice bath until addition was maintained under an N2 atmosphere overnight The phases were separated the organic phase washed with water (50 ml) dried with Na2SO4

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of glycerol (30 g, 326 mmol) and pyridine (25 ml) dissolved in DMF (300 ml) was added dropwise stearoyl chloride (10 g, 33 mmol) dissolved in DMF 100 ml9. The mixture was cooled on an ice bath until addition was complete, whereupon the reaction was maintained under an N2 atmosphere overnight. After 15 hours CH2CL2 (300 ml) and saturated NaHCO3 (aq) was added. The phases were separated and the organic phase washed with water (50 ml) and dried with Na2SO4. The mixture was cooled on an ice bath until addition was maintained under an N2 atmosphere overnight The phases were separated the organic phase washed with water (50 ml) dried with Na2SO4

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The experiment was carried out under the same conditions as in Example 3 but using a molar ratio of glycidol:stearic acid of 1.3:1. After 3 hours the amount of glycidol equivalent to the stearic acid had reacted and the mixture was cooled and worked up in a manner analogous to Example 1. There were obtained 116 grams of monostearin (80.9% yield) with the following properties: the mixture was cooled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.4 mole of stearic acid were heated to boiling (about 113° C.) under reflux with 280 grams of toluene and 0.29 gram of NaOH (water free) and, in the course of 20 minutes, 31.2 grams of glycidol dropped in. After a further 5 hours at this temperature, the glycidol was 99% reacted and the reaction ended. After working as in Example 1, there were obtained 123.5 grams (86%) of monostearin having the following properties: (about 113° C.) dropped in reacted

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Octadecanoic acid, monoester with 1,2,3-propanetriol