2-фенилэтанол химические свойства, назначение, производство
Химические свойства
Phenethyl alcohol is the main component of rose oils obtained from rose blossoms. It occurs in smaller quantities in neroli oil, ylang-ylang oil, carnation oil, and geranium oils. Since the alcohol is rather soluble in water, losses occur when essential oils are produced by steam distillation.
Phenylethyl alcohol is a colorless liquid with a mild rose odor. It can be dehydrogenated catalytically to phenylacetaldehyde and oxidized to phenylacetic acid (e.g.,with chromic acid). Its fatty acid esterswith lowermolecularmass, as well as some alkyl ethers, are valuable fragrance and flavor substances.
Вхождение
Reported found (as is or esterified) in several natural products: rose concentrate, rose absolute (60% or more)
and rose distillation waters; also found in the essential oils of neroli, ylang-ylang, narcissus, hyacinth, lily, tea leaves, Michelia champaca,
Pandamus odoratissimus, Congo and Réunion geranium, tobacco and other oils. It has been identified in wines. It has also been reported found in over 200 foods and beverages including apple, apricot, orange juice, orange peel, many berries, bilberry, cherry,
grapefruit, peach, raisin, blackberry, guava, grapes, melon, papaya, asparagus, cabbage, leek, potato, rutabaga, tomato, Mentha
oils, cinnamon, ginger, breads, butter, saffron, mustard, mango, many cheeses, butter, milk, cooked chicken, cognac, hop oil, beer,
rum, whiskies, cider, sherry, cocoa, coffee, tea, nuts, oats, honey, soybean, coconut meat, avocado, olive, passion fruit, plum, beans,
mushroom, starfruit, mango, tamarind, fruit brandies, fig, gin, rice, quince, radish, litchi, sukiyaki, calamus, licorice, buckwheat,
watercress, elderberry fruit, kiwifruit, loquat, Tahiti and Bourbon vanilla, mountain papaya, endive, lemon balm, clary sage, shrimps,
crab, Chinese quince, lamb’s lettuce, truffle and maté.
Использование
Phenylethyl alcohol is qualitatively and quantitatively one of the most important fragrance substances in the class of aliphatic alcohols. Phenylethyl alcohol is used frequently and in large amounts as a fragrance material. It is a popular component in rose-type compositions but is also used in other blossom notes. It is stable to alkali and, therefore, ideally suited for use in soap perfumes. Indeed, it could be used in fragrance, antimicrobial agents, organic synthesis, preservatives, and food additives.
Подготовка
From toluene, benzene or styrene.
Методы производства
Phenylethyl alcohol is prepared by reduction of ethyl phenylacetate
with sodium in absolute alcohol; by hydrogenation of phenylacetaldehyde
in the presence of a nickel catalyst; or by addition of
ethylene oxide or ethylene chlorohydrin to phenylmagnesium
bromide, followed by hydrolysis. Phenylethyl alcohol also occurs
naturally in a number of essential oils, especially rose oil.
Общее описание
Phenylethyl alcohol, is a primary aromatic alcohol of high boiling point, having a characteristic rose-like odor. It presents organoleptic properties and impacts the quality of the wine, distilled beverages, and fermented foods. It shows its presence in fresh beer and is responsible for the rose-like odor of well-ripened cheese. It is commercially and industrially an important flavor and is a component of a variety of foodstuffs such as ice cream, gelatin, candy, pudding, chewing gum, and non-alcoholic beverages. It is formed by yeasts during fermentation of alcohols either by decomposition of L-phenylalanine or metabolism of sugar substrates.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Угроза здоровью
Phenylethanol is an irritant of
the eyes and a teratogen in rats.
Фармацевтические приложения
Phenylethyl alcohol is used as an antimicrobial preservative in
nasal, ophthalmic, and otic formulations at 0.25–0.5% v/v
concentration; it is generally used in combination with other
preservatives.Phenylethyl alcohol has also been used on its own
as an antimicrobial preservative at concentrations up to 1% v/v in
topical preparations. At this concentration, mycoplasmas are
inactivated within 20 minutes, although enveloped viruses are
resistant.Phenylethyl alcohol is also used in flavors and as a
perfumery component, especially in rose perfumes.
Профиль безопасности
Moderately toxic by ingestion and skin contact. A skin and eye irritant. Experimental teratogenic effects. Other experimental reproductive effects. Causes severe central nervous system injury to experimental animals. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidzing materials. To fight fEe, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes
Безопасность
Phenylethyl alcohol is generally regarded as a nontoxic and
nonirritant material. However, at the concentration used to preserve
eye-drops (about 0.5% v/v) or above, eye irritation may occur.
LD50 (rabbit, skin): 0.79 g/kg
LD50 (rat, oral): 1.79 g/kg
Канцерогенность
Phenylethanol was not mutagenic in
bacterial assays, nor did it increase the number
of sister chromatid exchanges in human
lymphocytes.
Метаболизм
Phenylethyl alcohol is oxidized almost entirely to the corresponding acid (Williams. 1959).
хранилище
Phenylethyl alcohol is stable in bulk, but is volatile and sensitive to
light and oxidizing agents. It is reasonably stable in both acidic and
alkaline solutions. Aqueous solutions may be sterilized by
autoclaving. If stored in low-density polyethylene containers,
phenylethyl alcohol may be absorbed by the containers. Losses to
polypropylene containers have been reported to be insignificant
over 12 weeks at 30°C. Sorption to rubber closures is generally
small.
The bulk material should be stored in a well-closed container,
protected from light, in a cool, dry place.
Методы очистки
Purify the ethanol by shaking it with a solution of ferrous sulfate, and the alcohol layer is washed with distilled water and fractionally distilled. [Beilstein 6 IV 3067.]
Несовместимости
Incompatible with oxidizing agents and protein, e.g. serum.
Phenylethyl alcohol is partially inactivated by polysorbates,
although this is not as great as the reduction in antimicrobial
activity that occurs with parabens and polysorbates.
Регуляторный статус
Included in the FDA Inactive Ingredients Database (nasal,
ophthalmic, and otic preparations). Included in nonparenteral
medicines licensed in the UK. Included in the Canadian List of
Acceptable Non-medicinal Ingredients.
2-фенилэтанол препаратная продукция и сырье
сырьё
препарат