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Chemical Structure| 36653-82-4 Chemical Structure| 36653-82-4
Chemical Structure| 36653-82-4

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CAS No.: 36653-82-4

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1-Hexadecanol is a solid organic compound and a member of the alcohol class of compounds. It is produced from whale oil, or vegetable oils such as palm oil and coconut oil. 1-Hexadecanol has hydrating properties that makes it a suitable emulsifier and stabilizer in pharmaceutical formulations. It is also present in washable ointment base due to its dispersant abilities and stabilizing properties. 1-Hexadecanol has potential antimicrobial activity.

Synonyms: Palmityl alcohol

4.5 *For Research Use Only !

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Product Details of 1-Hexadecanol

CAS No. :36653-82-4
Formula : C16H34O
M.W : 242.44
SMILES Code : CCCCCCCCCCCCCCCCO
Synonyms :
Palmityl alcohol
MDL No. :MFCD00004760
InChI Key :BXWNKGSJHAJOGX-UHFFFAOYSA-N
Pubchem ID :2682

Safety of 1-Hexadecanol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of 1-Hexadecanol

* 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.

  • Downstream synthetic route of [ 36653-82-4 ]

[ 36653-82-4 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 36653-82-4 ]
  • [ 99-14-9 ]
  • [ 4964-56-1 ]
  • 2
  • [ 628-97-7 ]
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YieldReaction ConditionsOperation in experiment
98% With C32H36ClNO2P2Ru; potassium tert-butylate; hydrogen; In tetrahydrofuran; at 120℃; under 38002.6 Torr; for 20h;Autoclave; Green chemistry; General procedure: In a glove box in a nitrogen atmosphere, 3.33 mg of ruthenium complex 1c (0.005 mmol) Add to a 125-mL Parr autoclave, After adding 11.2 mg of potassium t-butoxide (0.1 mmol), Then take 2mL of tetrahydrofuran and add it to the kettle for a while. Finally, methyl benzoate (1.3615 g, 10 mmol) was added. After the autoclave is sealed, it is taken out of the glove box. Charge hydrogen to 50 atm. The mixture in the reaction kettle was heated and stirred in an oil bath at 120 C for 10 hours, The reactor was cooled to room temperature in a water bath and the remaining gas was slowly drained from the fume hood. Tridecane (50 muL) was added to the mixture as an internal standard, and the yield of methyl benzoate was determined by gas chromatography to be 99%.
92% With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen; In tetrahydrofuran; at 100℃; under 38002.6 - 76005.1 Torr; for 15h;Glovebox; Autoclave; General procedure: In a glove box, add a ruthenium complex Ia (0.3 to 0.7 mg, 0.0002 to 0.001 mmol) to a 300 mL autoclave,Potassium methoxide (35-700 mg, 0.5-10 mmol), tetrahydrofuran (4-60 mL), and ester compounds (10-200 mmol).After sealing the autoclave, take it out of the glove box and fill it with 50 100atm of hydrogen.The reaction kettle was heated and stirred in an oil bath at 100 C for 10 to 336 hours.After the reaction kettle was cooled in an ice-water bath for 1.5 hours, the excess hydrogen was slowly released.The solvent was removed from the reaction solution under reduced pressure, and the residue was purified with a short silica gel column to obtain an alcohol compound. The results are shown in Table 5.
  • 3
  • [ 629-54-9 ]
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  • 4
  • [ 6608-47-5 ]
  • [ 36653-82-4 ]
  • [ 66143-69-9 ]
  • 5
  • [ 71-41-0 ]
  • [ 629-54-9 ]
  • sodium [ No CAS ]
  • [ 36653-82-4 ]
  • 6
  • [ 5601-60-5 ]
  • [ 36653-82-4 ]
  • [ 123648-40-8 ]
  • [ 200925-72-0 ]
  • (R)-8-Methyl-decanoic acid hexadecyl ester [ No CAS ]
  • (S)-8-Methyl-decanoic acid hexadecyl ester [ No CAS ]
  • 8
  • [ 36653-82-4 ]
  • potassium hydroxide [ No CAS ]
  • [ 58066-85-6 ]
YieldReaction ConditionsOperation in experiment
[0184] The shampoo compositions illustrated in the following Examples illustrate specific embodiments of the shampoo compositions of the present invention, but are not intended to be limiting thereof. Other modifications can be undertaken by the skilled artisan without departing from the spirit and scope of this invention. These exemplified embodiments of the shampoo composition of the present invention provide enhanced conditioning benefits to the hair. [0185] The shampoo compositions illustrated in the following Examples are prepared by conventional formulation and mixing methods, an example of which is set forth hereinbelow. All exemplified amounts are listed as weight percents and exclude minor materials such as diluents, preservatives, color solutions, imagery ingredients, botanicals, and so forth, unless otherwise specified. [0186] The compositions illustrated in the examples were prepared in the following manner (all percentages are based on weight unless otherwise specified). [0187] For each of the compositions, 6-9% of ammonium laureth-3 sulfate, P43 oil, PureSyn6 oil, cationic polymers, 0-1.5% Ammonium Xylene Sulfonate, and 0-5% water was added to a jacketed mix tank and heated to about 74 C. with agitation to form a solution. Citric Acid, Sodium Citrate, Sodium Benzoate, Disodium EDTA, Cocamide MEA and 0.6-0.9% Cetyl alcohol, were added to the tank and allowed to disperse. Ethylene glycol distearate (EGDS) was then added to the mixing vessel, and melted. After the EGDS was well dispersed (after about 10 minutes) preservative was added and mixed into the surfactant solution. This mixture was passed through a heat exchanger where it was cooled to about 35 C. and collected in a finishing tank. As a result of this cooling step, the ethylene glycol distearate crystallized to form a crystalline network in the product. [0188] Separately about 20% of the water was heated to about 74 C. and the remainder of the Cetyl Alcohol, Stearyl Alcohol, and the Cationic Surfactant were added to it. After incorporation, this mixture was passed through a heat exchanger where it was cooled to about 35 C. As a result of this cooling step, the Fatty Alcohols and surfactant crystallized to form a crystalline gel network. [0189] These two premixes are the mixed together and the remainder of the surfactants, perfume, Dimethicone, Sodium Chloride or Ammonium Xylene Sulfonate for viscosity adjustment and the remainder of the water were added with ample agitation to insure a homogeneous mixture. [0190] Preferred viscosities range from about 5000 to about 9000 centipoise at 27 C. (as measured by a Wells-Brookfield model RVTDCP viscometer using a CP-41 cone and plate at 2/s at 3 minutes).
YieldReaction ConditionsOperation in experiment
EXAMPLES [0184] The shampoo compositions illustrated in the following Examples illustrate specific embodiments of the shampoo compositions of the present invention, but are not intended to be limiting thereof. Other modifications can be undertaken by the skilled artisan without departing from the spirit and scope of this invention. These exemplified embodiments of the shampoo composition of the present invention provide enhanced conditioning benefits to the hair. [0185] The shampoo compositions illustrated in the following Examples are prepared by conventional formulation and mixing methods, an example of which is set forth hereinbelow. All exemplified amounts are listed as weight percents and exclude minor materials such as diluents, preservatives, color solutions, imagery ingredients, botanicals, and so forth, unless otherwise specified. [0186] The compositions illustrated in the examples were prepared in the following manner (all percentages are based on weight unless otherwise specified). [0187] For each of the compositions, 6-9% of ammonium laureth-3 sulfate, P43 oil, PureSyn6 oil, cationic polymers, 0-1.5% Ammonium Xylene Sulfonate, and 0-5% water was added to a jacketed mix tank and heated to about 74 C. with agitation to form a solution. Citric Acid, Sodium Citrate, Sodium Benzoate, Disodium EDTA, Cocamide MEA and 0.6-0.9% Cetyl alcohol, were added to the tank and allowed to disperse. Ethylene glycol distearate (EGDS) was then added to the mixing vessel, and melted. After the EGDS was well dispersed (after about 10 minutes) preservative was added and mixed into the surfactant solution. This mixture was passed through a heat exchanger where it was cooled to about 35 C. and collected in a finishing tank. As a result of this cooling step, the ethylene glycol distearate crystallized to form a crystalline network in the product. [0188] Separately about 20% of the water was heated to about 74 C. and the remainder of the Cetyl Alcohol, Stearyl Alcohol, and the Cationic Surfactant were added to it. After incorporation, this mixture was passed through a heat exchanger where it was cooled to about 35 C. As a result of this cooling step, the Fatty Alcohols and surfactant crystallized to form a crystalline gel network. [0189] These two premixes are the mixed together and the remainder of the surfactants, perfume, Dimethicone, Sodium Chloride or Ammonium Xylene Sulfonate for viscosity adjustment and the remainder of the water were added with ample agitation to insure a homogeneous mixture. [0190] Preferred viscosities range from about 5000 to about 9000 centipoise at 27 C. (as measured by a Wells-Brookfield model RVTDCP viscometer using a CP-41 cone and plate at 2/s at 3 minutes).
  • 11
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  • [ 320-47-8 ]
  • [ 1132110-17-8 ]
  • 12
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  • [ 55357-38-5 ]
  • [ 58066-85-6 ]
  • 13
  • [ 111897-57-5 ]
  • [ 36653-82-4 ]
  • [ 58066-85-6 ]
YieldReaction ConditionsOperation in experiment
Various phosphocholine derivatives were synthesized using a three-step process as shown in FIGS. 1-2. Specifically, 0.484 grams of hexadecanol (n=15) (from Aldrich Chemical Company) was mixed with 20 milliliters of toluene and 100 milliliters of phosphoryl chloride (?POCl3?). The mixture was heated in an oil bath at 87 to 90 C. for 5 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuum. 50 milliliters of methylene chloride and 1.38 grams of choline tosylate were then stirred into the mixture at room temperature for 40 to 50 hours. This reaction mixture was concentrated by a rotavaporator and the resulting residue was mixed with 1.5 milliliters of water. The residue was stirred at room temperature for 5 hours and concentrated with a nitrogen stream to give crude hexadecyl phosphocholine. Tetradecyl phosphocholine (C14 chain) and docosanoyl phosphocholine (C22 chain) were also synthesized using the technique described above, except that tetradecanol (n=13) and docosanoyl alcohol (n=21) were used to as starting materials instead of hexadecanol. Further, as shown in FIG. 2, the procedure set forth above was also used to synthesize hexadecyl thiophosphocholine, except that thiophosphoryl chloride was used instead of phosphoryl chloride. The expected molecular ion and the corresponding mass spectral results for each synthesized phosphocholine or thiophosphocholine derivatives were determined using mass spectral analysis. The results are shown below in Table 1.
  • 15
  • [ 36653-82-4 ]
  • [ 3543-75-7 ]
  • [ 1609623-06-4 ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; Preparation of 4-{5-[Bis-(chloroethyl)-amino]-l-methyl-lH-benzimidazol-2-yl}butyric acid pentadecyl ester (<strong>[3543-75-7]bendamustine</strong> Ci ester): A 250 mL three neck round bottom flask was equipped with an overhead stirrer, thermocouple, temperature controller and nitrogen sweep then charged with 10.0 g (25.34 mmol) of <strong>[3543-75-7]<strong>[3543-75-7]bendamustine</strong> hydrochloride</strong>, 5.85 g (25.6 mmol, 1.01 eq) of pentadecanol, 5.3 g (25.6 mmol, 1.01 eq) of dicyclohexylcarbodiimide (DCC), 100 mL of MDC and 0.31 g (2.54 mmol, 0.1 eq) of DMAP. The reaction was stirred at room temperature overnight at which time an in process analysis indicated the reaction was complete. Solids were removed by vacuum filtration and washed with 25 mL of MDC. The filtrate was washed with saturated aqueous sodium bicarbonate solution (2 X 100 mL), DI water (1 X 100 mL) and brine (1 X 100 mL) before drying over sodium sulfate, filtering and concentrating to dryness in vacuo to an off-white solid. This solid was triturated with 25 mL of MDC and the solid impurities were removed by vacuum filtration and washed with 5 mL of MDC. The filtrate was concentrated to dryness in vacuo to yield 10.8 g (19.0 mmol, 75%) of the product as an off-white solid with an HPLC purity of 94.6A%. NMR (400 MHz, CDC13) delta 7.17 (d, J= 8.76 Hz, 1H), 7.08 (d, J= 2.32 Hz, 1H), 6.78 (dd, J= 2.4, 8.76 Hz, 1H), 4.05 (t, J= 6.8 Hz, 2 H), 3.72 (m, 4H), 3.69 (s, 3H), 3.63 (m, 4H), 2.91 (t, J= 7.4 Hz, 2H), 2.49 (t, J= 7.08 Hz, 2H), 2.18 (m, 2H), 1.60 (m, 2H), 1.32 (m, 24H), 0.88 (t, J= 6.68 Hz, 3H).
  • 16
  • [ 36653-82-4 ]
  • 2-(((2-cyanoethoxy)(diisopropylamino)phosphaneyl)oxy)-N,N,N-trimethylethan-1-aminium tetraphenylborate [ No CAS ]
  • [ 58066-85-6 ]
 

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