2-フェニルエチルアルコール

外観

無色～ほとんど無色, 澄明の液体

定義

本品は、次の化学式で表される芳香族アルコールである。

溶解性

水に微溶 (2%)。エタノール, エーテル等有機溶媒に易溶。エタノールに極めて溶けやすく、水にやや溶けにくい。

用途

医薬的補助剤(抗微生物)、っ風味剤、香料(特にバラ香料)(MERCK(14TH, 2006))

用途

花精油調合剤及び化粧水に用いる。また防腐剤としても用いられる。

化粧品の成分用途

防腐剤、溶剤、香料

効能

抗菌薬

化学的特性

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.

天然物の起源

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.

使用

phenethyl alcohol is used to mask odor and also as a preservative.

製造方法

From toluene, benzene or styrene.

調製方法

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.

一般的な説明

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.

健康ハザード

Phenylethanol is an irritant of the eyes and a teratogen in rats.

応用例（製薬）

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.

安全性プロファイル

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

安全性

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

発がん性

Phenylethanol was not mutagenic in bacterial assays, nor did it increase the number of sister chromatid exchanges in human lymphocytes.

代謝

Phenylethyl alcohol is oxidized almost entirely to the corresponding acid (Williams. 1959).

貯蔵

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.

純化方法

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.]

不和合性

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.

規制状況(Regulatory Status)

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.