Phenethyl alcohol

Chemical properties

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.

Chemical properties

Phenethyl alcohol has a characteristic rose-like odor and an initially slightly bitter taste, then sweet and reminiscent of peach.

Occurrence

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.

The Uses of Phenethyl alcohol

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

The Uses of Phenethyl alcohol

Pharmaceutic aid (antimicrobial). In flavors and perfumery (esp rose perfumes).

The Uses of Phenethyl alcohol

In fragrance; antimicrobial agent; in organic synthesis; preservative, food additive

What are the applications of Application

2-Phenylethanol is an alcohol potentially used as an anti-microbial

Production Methods

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.

Preparation

From toluene, benzene or styrene.

Definition

ChEBI: 2-phenylethanol is a primary alcohol that is ethanol substituted by a phenyl group at position 2. It has a role as a fragrance, a Saccharomyces cerevisiae metabolite, a plant metabolite, an Aspergillus metabolite and a plant growth retardant. It is a primary alcohol and a member of benzenes.

Aroma threshold values

Detection: 0.015 ppb to 3.5 ppm; recognition: 1.2 ppm. Aroma characteristics at 1.0%: floral honey, yeasty bready, musty fresh and sweet.

Taste threshold values

Taste characteristics at 20 ppm: mushroom-like, rose floral, sweet, rosy, bready with honey nuances.

Synthesis Reference(s)

Chemistry Letters, 18, p. 619, 1989
Journal of the American Chemical Society, 100, p. 4888, 1978 DOI: 10.1021/ja00483a042
Tetrahedron Letters, 18, p. 3263, 1977 DOI: 10.1016/S0040-4039(01)83213-5

General Description

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.

Health Hazard

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

Pharmaceutical Applications

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.

Safety Profile

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

Safety

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

Carcinogenicity

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

Metabolism

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

storage

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.

Purification Methods

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.]

Incompatibilities

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.

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.