1-Тетрадеканол

Химические свойства

white low melting solid or flakes

Использование

1-Tetradecanol is used as an ingredient in cosmetics such as cold creams. It is an active intermediate in the chemical synthesis of sulfated alcohol. It is also employed in the fabrication of temperature-regulated drug release system based on phase-change materials. It plays a vital role in filling the hollow interiors of gold nanocages in the fabrication of new theranostic system, which has unique feature of photoacoustic imaging.

Методы производства

Myristyl alcohol is found in spermaceti wax and sperm oil, and may be synthesized by sodium reduction of fatty acid esters or the reduction of fatty acids by lithium aluminum hydride. It can also be formed from acetaldehyde and dimethylamine.

Определение

ChEBI: 1-Tetradecanol is a long-chain fatty alcohol that is tetradecane in which one of the terminal methyl hydrogens is replaced by a hydroxy group It is a long-chain primary fatty alcohol, a fatty alcohol 14:0 and a primary alcohol.

Подготовка

1-Tetradecanol is prepared from the head oil of the Sperm Whale via the acid and the ester.

Общее описание

Colorless thick liquid (heated) with a faint alcohol odor. Solidifies and floats on water.

Реакции воздуха и воды

Insoluble in water.

Профиль реактивности

1-Tetradecanol is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Угроза здоровью

Low toxicity. Overexposure causes some central nervous system depression. Prolonged skin contact causes skin irritation.

Фармацевтические приложения

Myristyl alcohol is used in oral, parenteral, and topical pharmaceutical formulations. It has been evaluated as a penetration enhancer in melatonin transdermal patches in rats.
Myristyl alcohol has also been tested as a bilayer stabilizer in niosome formulations containing ketorolac tromethamine,and zidovudine.Niosomes containing myristyl alcohol showed a considerably slower release rate of ketorolac tromethamine than those containing cholesterol.This was also observed with the zidovudine formulation.

Безопасность

Myristyl alcohol is used in oral parenteral, and topical pharmaceutical formulations. The pure form of myristyl alcohol is mildly toxic by ingestion and may be carcinogenic; experimental tumorigenic data are available.It is also a human skin irritant. In animal studies of the skin permeation enhancement effect of saturated fatty alcohols, myristyl alcohol exhibited a lower effect when compared with decanol, undecanol, or lauryl alcohol but caused greater skin irritation.A study investigating contact sensitization to myristyl alcohol revealed that patch testing of myristyl alcohol 10% petrolatum should not be carried out owing to observed irritant effects; thus the use of a lower concentration of myristyl alcohol for such tests (5% petrolatum) was recommended.Myristyl alcohol has been associated with some reports of contact allergy.(8,9)A moderate-to-severe erythema and moderate edema are seen when 75 mg is applied to human skin intermittently in three doses over 72 hours.
LD₅₀(rabbit, skin): 7.1 g/kg
LD₅₀(rat, oral): 33.0 g/kg

хранилище

The bulk material should be stored in a well-closed container in a cool, dry place.

Методы очистки

Crystallise the alcohol from aqueous EtOH. It has also been purified by zone melting. [Beilstein 1 IV 1864.]

Несовместимости

Myristyl alcohol is combustible when exposed to heat or flame. It can react with oxidizing materials. When heated to decomposition, it emits acrid smoke and irritating fumes.

Регуляторный статус

Included in the FDA Inactive Ingredients Database (oral tablet: sustained-release; and topical formulations: cream, lotion, suspension). Included in nonparenteral (topical cream) formulations licensed in the UK.