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| CAS No. : | 540-10-3 |
| Formula : | C32H64O2 |
| M.W : | 480.85 |
| SMILES Code : | CCCCCCCCCCCCCCCC(OCCCCCCCCCCCCCCCC)=O |
| English Name : | Hexadecyl palmitate |
| MDL No. : | MFCD00053739 |
| InChI Key : | PXDJXZJSCPSGGI-UHFFFAOYSA-N |
| Pubchem ID : | 10889 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 99.5% | With zirconium(IV) oxychloride In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 98.7% | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 97% | With choline chloride; zinc(II) chloride at 110℃; for 10h; |
| 96% | In hexane at 25℃; for 4h; | |
| 88% | With bromine; triphenylphosphine for 0.5h; Ambient temperature; | |
| With diethyl ether; pig's pancreas esterase; acetone | ||
| With sodium deoxycholate; pig's pancreas esterase | ||
| With pig's pancreas esterase; sodium Oleate | ||
| With toluene-4-sulfonic acid; benzene | ||
| In 1,1,1-trichloroethane at 25℃; Yield given; | ||
| In water at 70 - 75℃; for 6h; | 1 COMPARATIVE EXAMPLE 1; This example demonstrates a typical prior art process of using a conventional acid catalyst. A reactor was charged with palmitic acid (7.79 parts), cetyl alcohol (14.71 parts) and water (6.47 parts). After warming under agitation to 70-75° C., sulphuric acid (10% aqueous solution, 1.15 parts) was added and the mixing temperature maintained for six hours. The reaction mixture was biphasic. A sample of the mixture revealed that 8.2 mole % of the palmitic acid was converted into the ester. | |
| In water at 70 - 75℃; for 6h; | 18; 23; 28 EXAMPLES 14-33; Experiments were conducted to study the effect of the amount and type of hydrolyzable catalyst. The reactor was charged with palmitic acid, cetyl alcohol, the sodium salt of the hydrolyzable catalyst, and water. After warming under agitation to 70-75° C., sulphuric acid is added and the mixing and temperature maintained for 6 hours. Samples of the mixture are taken to determine the mole conversion of palmitic acid into ester. The results are shown in Table 3 below: | |
| In water at 70 - 75℃; for 6h; | 17; 22; 27 EXAMPLES 14-33; Experiments were conducted to study the effect of the amount and type of hydrolyzable catalyst. The reactor was charged with palmitic acid, cetyl alcohol, the sodium salt of the hydrolyzable catalyst, and water. After warming under agitation to 70-75° C., sulphuric acid is added and the mixing and temperature maintained for 6 hours. Samples of the mixture are taken to determine the mole conversion of palmitic acid into ester. The results are shown in Table 3 below: | |
| In water at 70 - 75℃; for 6h; | 3; 4; 5; 6; 7; 8; 9; 10; 11; 14; 19; 24 EXAMPLES 3-7; Experiments were conducted to determine the preferred ratio of carboxylic acid to alcohol. A reactor was charged with various amounts of palmitic acid, cetyl alcohol, sodium lauryl sulphate, (10% aqueous solution, 6.75 parts), and water (0.29 parts). After warming under agitation to 70-75° C., sulphuric acid (10% aqueous solution, 1.26 parts) was added and the mixing and temperature maintained for six hours. Samples of the reaction products were taken to determine the mole % conversion of palmitic acid into ester. The results are shown in Table 1 below:; Experiments were conducted to study the amount and type of strong acid. A reactor was charged with palmitic acid (1.56 parts), cetyl alcohol (2.94 parts), sodium lauryl sulphate (0.14 parts), and water. After warming under agitation at 70-75° C., the strong acid was added and the mixing and temperature maintained for 6 hours. Samples of the mixture were taken to determine the mole conversion of the palmitic acid into ester. The results are shown in Table 2 below:; Experiments were conducted to study the effect of the amount and type of hydrolyzable catalyst. The reactor was charged with palmitic acid, cetyl alcohol, the sodium salt of the hydrolyzable catalyst, and water. After warming under agitation to 70-75° C., sulphuric acid is added and the mixing and temperature maintained for 6 hours. Samples of the mixture are taken to determine the mole conversion of palmitic acid into ester. The results are shown in Table 3 below: | |
| In water at 70 - 75℃; for 6h; | 32 EXAMPLES 14-33; Experiments were conducted to study the effect of the amount and type of hydrolyzable catalyst. The reactor was charged with palmitic acid, cetyl alcohol, the sodium salt of the hydrolyzable catalyst, and water. After warming under agitation to 70-75° C., sulphuric acid is added and the mixing and temperature maintained for 6 hours. Samples of the mixture are taken to determine the mole conversion of palmitic acid into ester. The results are shown in Table 3 below: | |
| In water at 70 - 75℃; for 6h; | 30 EXAMPLES 14-33; Experiments were conducted to study the effect of the amount and type of hydrolyzable catalyst. The reactor was charged with palmitic acid, cetyl alcohol, the sodium salt of the hydrolyzable catalyst, and water. After warming under agitation to 70-75° C., sulphuric acid is added and the mixing and temperature maintained for 6 hours. Samples of the mixture are taken to determine the mole conversion of palmitic acid into ester. The results are shown in Table 3 below: | |
| In water at 70 - 75℃; for 6h; | 29 EXAMPLES 14-33; Experiments were conducted to study the effect of the amount and type of hydrolyzable catalyst. The reactor was charged with palmitic acid, cetyl alcohol, the sodium salt of the hydrolyzable catalyst, and water. After warming under agitation to 70-75° C., sulphuric acid is added and the mixing and temperature maintained for 6 hours. Samples of the mixture are taken to determine the mole conversion of palmitic acid into ester. The results are shown in Table 3 below: | |
| In water at 70 - 75℃; for 6h; | 31 EXAMPLES 14-33; Experiments were conducted to study the effect of the amount and type of hydrolyzable catalyst. The reactor was charged with palmitic acid, cetyl alcohol, the sodium salt of the hydrolyzable catalyst, and water. After warming under agitation to 70-75° C., sulphuric acid is added and the mixing and temperature maintained for 6 hours. Samples of the mixture are taken to determine the mole conversion of palmitic acid into ester. The results are shown in Table 3 below: | |
| In water at 70 - 75℃; for 6h; | 33 EXAMPLES 14-33; Experiments were conducted to study the effect of the amount and type of hydrolyzable catalyst. The reactor was charged with palmitic acid, cetyl alcohol, the sodium salt of the hydrolyzable catalyst, and water. After warming under agitation to 70-75° C., sulphuric acid is added and the mixing and temperature maintained for 6 hours. Samples of the mixture are taken to determine the mole conversion of palmitic acid into ester. The results are shown in Table 3 below: | |
| In water at 70 - 75℃; for 6h; | 16; 21; 26 EXAMPLES 14-33; Experiments were conducted to study the effect of the amount and type of hydrolyzable catalyst. The reactor was charged with palmitic acid, cetyl alcohol, the sodium salt of the hydrolyzable catalyst, and water. After warming under agitation to 70-75° C., sulphuric acid is added and the mixing and temperature maintained for 6 hours. Samples of the mixture are taken to determine the mole conversion of palmitic acid into ester. The results are shown in Table 3 below: | |
| In water at 70 - 75℃; for 6h; | 15; 20; 25 EXAMPLES 14-33; Experiments were conducted to study the effect of the amount and type of hydrolyzable catalyst. The reactor was charged with palmitic acid, cetyl alcohol, the sodium salt of the hydrolyzable catalyst, and water. After warming under agitation to 70-75° C., sulphuric acid is added and the mixing and temperature maintained for 6 hours. Samples of the mixture are taken to determine the mole conversion of palmitic acid into ester. The results are shown in Table 3 below: | |
| With sodium dodecyl-sulfate In water at 70 - 75℃; for 6h; | 12 EXAMPLES 8-13; Experiments were conducted to study the amount and type of strong acid. A reactor was charged with palmitic acid (1.56 parts), cetyl alcohol (2.94 parts), sodium lauryl sulphate (0.14 parts), and water. After warming under agitation at 70-75° C., the strong acid was added and the mixing and temperature maintained for 6 hours. Samples of the mixture were taken to determine the mole conversion of the palmitic acid into ester. The results are shown in Table 2 below: | |
| With sodium dodecyl-sulfate In water at 70 - 75℃; for 6h; | 13 EXAMPLES 8-13; Experiments were conducted to study the amount and type of strong acid. A reactor was charged with palmitic acid (1.56 parts), cetyl alcohol (2.94 parts), sodium lauryl sulphate (0.14 parts), and water. After warming under agitation at 70-75° C., the strong acid was added and the mixing and temperature maintained for 6 hours. Samples of the mixture were taken to determine the mole conversion of the palmitic acid into ester. The results are shown in Table 2 below: | |
| 73.8 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 73.8 %Chromat. | In 1,3,5-trimethyl-benzene at 165℃; for 12h; | |
| 72.4 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 99.2 %Chromat. | In 1,3,5-trimethyl-benzene at 165℃; for 24h; | |
| 100 %Chromat. | In tetralin at 207℃; for 24h; | |
| 86 %Chromat. | In 1,3,5-trimethyl-benzene at 165℃; for 24h; | |
| 41 %Chromat. | In 1,3,5-trimethyl-benzene at 165℃; for 24h; | |
| 98.0 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 81.5 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 93.5 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 97.5 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 98.6 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 88.0 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 95.6 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 53.6 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 99.2 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 92.5 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 84.3 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 89.1 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 95.8 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 88.2 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 99.6 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 70.5 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 32.3 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 49.2 %Chromat. | In 1,3,5-trimethyl-benzene at 162℃; for 24h; | |
| 61 - 100 %Chromat. | In 1,3,5-trimethyl-benzene at 165℃; for 24h; | |
| 41 - 53 %Chromat. | In m-xylene at 140℃; for 24h; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 55% | With hydrogen In neat (no solvent) at 20 - 200℃; for 24h; Autoclave; High pressure; | |
| With copper chromite; hydrogen at 360℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With quinoline; chloroform anfangs unter Kuehlung, dann bei Zimmertemperatur; | ||
| With diethyl ether; magnesium | ||
| With pyridine |
| In pyridine; chloroform |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dimethylsulfide borane complex; pyridinium chlorochromate 1) THF, reflux, 1 h, 2.) CH2Cl2, reflux, 1 h; Yield given. Multistep reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 61% 2: 22% | With trimethylamine borane In xylene for 9h; Heating; | |
| With hydrogen; zirconium(IV) oxide In dodecane at 20 - 260℃; Autoclave; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 50% | With triethylamine In dichloromethane at 0 - 20℃; | 5 General procedure: . A three neck round bottom flask was equipped with dropping funnel, drying tube (with CaCl2) and thermometer and charged with 1.0 eq. alcohol, 1.2 eq. triethylamine and dichloromethane (concentration: 1.0 mmol alcohol in 4 ml dichloromethane). The mixture in the flask was cooled down to 0°C and the dichloromethane solution of 1.0 eq. acyl chloride (concentration: 1.0 mmol acyl chloride in 1.0 ml dichloromethane) was added dropwise. The reaction mixture was left to warm to room temperature and stirred for overnight. The reaction was monitored by TLC (hexane/ethyl acetate 9/1). After overnight the volatiles were removed under reduced pressure and filtered the triethylamine hydrochloride salt. The filtrate was evaporated onto silica gel under reduced pressure, and it was purified by flash column chromatography. |
| Hexadecansaeure, Hexadecylalkohol; | ||
| Saeure, Alkohol, SOCl2; |
| Me-(CH2)14-CH2OH <CuCO3/ZnCO3>; | ||
| Palmitic acid, cetyl alcohol in THF, p-CH3C6H4SO3H, molecular sieve; | ||
| Palmitylalkohol, Palmitinsaeurechlorid; | ||
| Hexadecan-1-ol-Lsg., tert-Butylchromat (ca. 30grad), neben Palmitinsaeure; | ||
| Methylpalmitat, Essigester, Na-methylat; | ||
| Cetylalkohol (Essigs., Acn., 15grad), CrO3 (wss. H2SO4, 15grad, 30 min); | ||
| In another aspect the invention is the use, in the manufacture of oral dosage units for the treatment or prophylaxis of irritable bowel syndrome in a mammal, of (a) cetyl myristate or (b) cetyl myristate and cetyl palmitate or, (c) cetyl palmitate. |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| at 180℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 1-(14)C cetyl alcohol In acetone at 40℃; for 1h; transesterification with enzyme from Sinapis alba L.; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With [14C]-Cholesterol In acetone at 40℃; for 1h; transesterification with enzyme from Sinapis alba L.; influence of incubation time and <1-14C>n-hexadecanol concentration on ester formation; double pH optima: 6.4, 8.4; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Irradiation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With phosphoric acid In hexane; water for 8.5h; Heating / reflux; | A Experiment A.-Hexane Solvent; Myristic acid/palmitic acid, 200 cc. of 85% phosphoric acid and 1800 ml. of hexane were mixed, heated to reflux and then 251 grams of cetyl alcohol added in 30 min. The mixture was refluxed further for 8 hours. Then the hot mixture consisted of a muddy acid layer and a opaque solvent layer which could not be separated by decantation or filtration. The mixture was further diluted with three volumes of hexane causing the slushy hexane layer to further soften enough to be separated from aqueous layer. The hexane layer was then cooled to bring about crystallization of fatty ester. The weight of cetyl myristate isolated was 294 grams which had a melting point of 54-59° C. The conversion, based on the cetyl alcohol used, was 63.71% | |
| With phosphoric acid In n-heptane; water for 18h; Heating / reflux; | B Experiment B.-Heptane Solvent; Myristic acid/palmitic acid, 200 cc. of phosphoric acid, and 1800 ml. of heptane were mixed, heated to reflux and then 251 grams of cetyl alcohol refluxed further for 18 hours and separated as in example A. On crystallization, the cetyl myristate obtained was much darker in colour then in Experiment-A. [0030] It is evident that this process as exemplified by Experiment B is even less satisfactory than that set forth in Experiment-A | |
| With phosphoric acid In water; toluene at 92℃; for 38.5h; Heating / reflux; | 1 EXAMPLE 1; Toluene Solvent; 1800 cc. of toluene, myristic acid/palmitic acid and 400 cc. of 85% phosphoric acid were mixed, heated to 92° C. and 251 grams of cetyl alcohol was introduced over a 30-minute period. When the addition was complete, the reaction mixture was further refluxed for 38 hours. The hot reaction mixture was a two phase system consisting of a toluene layer and an aqueous phosphoric acid layer. No solid material was present. The hot toluene layer was separated and mixed with charcoal to remove the undesired colouring matter. [0037] The filtrate was cooled to bring about crystallization of cetyl myristate which was isolated by filtration. The weight of cetyl myristate isolated was 436 grams which had a melting point of 54-58° C. The percentage conversion based on the cetyl alcohol employed was 92.3 percent |
| With phosphoric acid In water; xylene at 105℃; for 1h; | 2; 3 EXAMPLE 2; Xylene Solvent; Myristic acid/palmitic acid, 250 grams of 85% phosphoric acid and 1000 cc. of xylene were mixed in a three neck flask provided with thermometer, agitator and reflux condenser. The temperature was increased to 105 with good agitation and 55 grams of cetyl alcohol was introduced over a one-hour period. After the reaction the supernatant xylene layer was drawn off, and the lower phosphoric acid layer was preserved for use in the following run. [0040] The xylene layer on cooling deposited a crystalline solid which weighed 154 gms. This material consisted of cetyl myristate and any unreacted fatty acid. The crude product was easily purified by recrystallization from hot xylene to yield pure cetyl myristate M.P.=54-56° C; EXAMPLE 3; Xylene Solvent; Myristic acid/palmitic acid, 400 cc. of 85% phosphoric acid and 2400 cc. of xylene were mixed in a three neck flask provided with a thermometer, agitator and reflux condenser. The temperature was raised to 105° C. with good agitation and 251 grams of cetyl alcohol was introduced with good agitation over a 1-hour period. The mixture reflux for 36 hour. Next, the supernatant xylene layer was drawn off, and the lower phosphoric acid layer was preserved for use in a subsequent run. The xylene layer on cooling deposited a crystalline solid which weighed 438 grams. This crude material was substantially cetyl myristate and was purified by recrystallization from hot xylene so as to yield pure cetyl myristate having a melting point of 54-56° C. [0045] The water which is formed by the employment of cetyl alcohol in the course of the reaction as in Example 2 dilutes the reaction mixture but can be readily removed by azeotropic distillation of the reaction mixture | |
| With phosphoric acid In water at 95℃; for 0.5h; | C Experiment C.-Alkylation in Absence of a Solvent; Myristic acid/palmitic acid, 400 cc. of 85% phosphoric acid were mixed, heated to 95 C., and 251 grams of cetyl alcohol was added over a period of 30 minutes. The mixture further heated in vacuum and then on cooling. The reaction mixture, which contained a finely divided white solid, was diluted to 3000 ml. with water cooled to 25 C. and filtered. The white product was treated with hot water, and the mixture filtered hot to remove any alcohol. [0033] The unreacted fatty acid was present in a large quantity. The reaction was not complete |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 4 Composition No. 1: 70% glyceryl stearate & 10% cetearyl alcohol & 10% coco-glycerides & 10% cetyl palmitate: 0.1% to 5% Potassium cetyl phosphate: 0.1% to 2% Carbomer: 0.1% to 2% Fragrance: 0.1% to 1% Xanthan gum: 0.1% to 1% Purified water: QSP 100% |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogen In dodecane at 20 - 260℃; Autoclave; |