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Product Details
Edible spices |
Phenethyl alcohol is a kind of edible spices, and naturally exists in neroli, rose oil, geranium oil and other oils, because it has a soft, pleasant and persistent rose fragrance and is widely used in various kinds of flavors and cigarette flavor. It is dispensing rose scent, food additives, the main raw material for rose scent flavor, stable on alkali, which are widely used in soap fragrance, is essence blending all rose scent series of spices, because it does not dissolve in water, it is often used in the making up water, soap and orange flower, purple, etc. It is also used in the blending of flavor. Because the Phenethyl alcohol has a good antibacterial efficiency, it can be used in the ophthalmic solution. At present there are main three synthesis methods as following: 1, by styrene via halogenation, saponification, hydrogenation, distillation. 2, and microorganism fermentation in yeast by bioconversion. 3, calcium carbide, benzene as raw material preparation of benzyl ethanol, reaction equations are as follows: 1)CaC2+2H2O=Ca(OH)2+C2H2 2)C6H6+C2H2=C6H6CHCH2(Styrene) 3)C6H6CHCH2+H2O=C6H6CH2CH2OH(Phenylethyl alcohol) |
Chemical Properties |
Phenethyl alcohol is a clear, colorless liquid with an odor of rose oil. It has a burning taste that irritates and then anesthetizes mucous membranes. Phenethyl Alcohol (PEA) is an aromatic alcohol that is used as a fragrance and an antimicrobial preservative in cosmetic formulations. It is active at pH 6 or less and is inactivated by nonionic detergents including polysorbate-80. PEA is also a widely used fragrance material that imparts a rose character to perfume compositions. Almost all rose fragrances and other floral-type perfumes contain PEA, and PEA is used extensively for many other fragrance applications because it blends ell. PEA is metabolized to phenylacetic acid in mammals. In humans, it is excreted in urine as the conjugate phenylacetylglutamine. |
Uses |
Phenylethyl alcohol is qualitatively and quantitatively one of the most important fragrance substances that belongs to the class of araliphatic alcohols. Phenylethyl alcohol is used frequently and in large amounts as a fragrance material. It is a popular component in rose-type compositions, but it is also used in other blossom notes. It is stable to alkali and, therefore, ideally suited for use in soap perfumes. |
Production |
Many syntheticmethods are known for preparing phenylethyl alcohol; the following are currently of industrial importance: 1) Friedel–Crafts reaction of benzene and ethylene oxide: In the presence of molar quantities of aluminum chloride, ethylene oxide reacts with benzene to give an addition product, which is hydrolyzed to phenylethyl alcohol: Formation of by-products, such as 1,2-diphenylethane, is largely avoided by using an excess of benzene at low temperature. Special purification procedures are required to obtain a pure product that is free of chlorine and suitable for use in perfumery. 2) Hydrogenation of styrene oxide: Excellent yields of phenylethyl alcohol are obtainedwhen styrene oxide is hydrogenated at low temperature, using Raney nickel as a catalyst and a small amount of sodium hydroxide. |
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. |
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. |
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, 1989Journal of the American Chemical Society, 100, p. 4888, 1978 DOI: 10.1021/ja00483a042Tetrahedron 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. |
Who Evaluation |
Evaluation year: 2002 |
InChI:InChI=1/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
-
The 2-phenylethanol production by tradit...
Heteroatom doping has been demonstrated ...
Three hectorites were synthesised at dif...
A tetrahedral stannasilsesquioxane compl...
The effect of Cu(I) salt (i.e., CuCN, Cu...
Oxygenation of hydrocarbons by atmospher...
(Chemical Equation Presented) Tamed OATS...
2-Phenylethanol is formed via an in situ...
A heterogeneous palladium(II) catalyst a...
Three mononuclear iron complexes and one...
-
Exploring both high-performance catalyti...
-
Abstract We show that a monocationic CpR...
The volatile compounds, 2-phenylacetalde...
The reductive opening of epoxides repres...
Different carboxy-functionalized imidazo...
Petroleum hydrocarbons are our major ene...
The metal-catalyzed hydrogenolysis of ep...
styrene oxide
1-Phenylethanol
2-phenylethanol
Conditions | Yield |
---|---|
With
[carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen;
In
toluene;
at 75 ℃;
for 24h;
under 37503.8 Torr;
Pressure;
Temperature;
Reagent/catalyst;
regioselective reaction;
Catalytic behavior;
|
99% |
With
lithium triethylborohydride;
In
tetrahydrofuran;
at 0 ℃;
for 0.0833333h;
Product distribution;
|
97% 3% |
With
Li(1+)*C12H28AlO3(1-);
In
tetrahydrofuran; hexane;
at 0 ℃;
for 0.17h;
Yields of byproduct given;
|
95% |
With
Li(1+)*C12H28AlO3(1-);
In
tetrahydrofuran; hexane;
at 0 ℃;
for 0.17h;
Yield given. Title compound not separated from byproducts;
|
95% |
With
dibutylmagnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane;
In
tetrahydrofuran;
at 40 ℃;
for 24h;
Solvent;
Temperature;
regioselective reaction;
|
95% |
With
sodium tetrahydroborate; alpha cyclodextrin;
In
water;
for 48h;
Title compound not separated from byproducts;
Ambient temperature;
|
17% 66% |
With
methyltriphenylphosphonium tetrahydroborate; zinc(II) chloride;
In
dichloromethane;
at 20 ℃;
for 1h;
|
63% 21% |
With
sodium tetrahydroborate; cyclomaltooctaose;
In
water;
for 48h;
Title compound not separated from byproducts;
Ambient temperature;
|
53% 24% |
With
sodium tetrahydroborate; alpha cyclodextrin;
In
water;
for 48h;
Product distribution;
Ambient temperature;
presence of β-, and γ-cyclodextrin; kinetic resolution; further epoxides;
|
31% 23% |
With
sodium tetrahydroborate; β‐cyclodextrin;
In
water;
for 48h;
Product distribution;
Ambient temperature;
other epoxides, other cyclodextrins;
|
66 % Chromat. 17 % Chromat. |
With
aluminium; nickel dichloride;
In
tetrahydrofuran;
for 0.0833333h;
other epoxides;
|
10 % Chromat. 75 % Chromat. |
With
sodium tetrahydroborate;
In
ethanol;
at 45 ℃;
for 3h;
Product distribution;
var. solvents, times;
|
|
With
water; diisobutylaluminium hydride;
Product distribution;
other organoaluminum reagents; regioselectivity;
|
|
With
sodium tetrahydroborate;
In
methanol; tert-butyl alcohol;
for 2h;
Product distribution;
Heating;
other solvents, other molar ratio;
|
|
With
sodium tetrahydroborate; β‐cyclodextrin;
In
water;
for 72h;
Ambient temperature;
|
3 % Chromat. 48 % Chromat. |
With
2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium iodide;
In
1,2-dimethoxyethane;
at 70 ℃;
for 1h;
Yield given. Yields of byproduct given;
|
|
With
aluminium; nickel dichloride;
In
tetrahydrofuran;
for 0.0833333h;
|
75 % Chromat. 10 % Chromat. |
With
2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium iodide;
In
1,2-dimethoxyethane;
for 1.5h;
Yield given;
Heating;
|
|
With
methanol; sodium tetrahydroborate;
In
tert-butyl alcohol;
for 1h;
Yield given. Yields of byproduct given;
Heating;
|
|
With
sodium tetrahydroborate;
In
isopropyl alcohol;
for 2h;
Yield given. Yields of byproduct given;
Heating;
|
|
With
sodium aluminum tetrahydride;
In
tetrahydrofuran;
at 0 ℃;
for 6h;
Yield given. Yields of byproduct given;
|
|
With
triethylamine alane;
In
tetrahydrofuran;
for 6h;
Ambient temperature;
|
23 % Chromat. 77 % Chromat. |
With
lithium aluminium tetrahydride; water;
Yield given. Multistep reaction. Yields of byproduct given;
1) THF, 25 deg C, 1 h;
|
|
With
1-Methylpyrrolidine; lithium aluminium tetrahydride;
In
tetrahydrofuran;
at 0 ℃;
for 1h;
Yield given. Yields of byproduct given;
|
|
With
methanol; lithium borohydride; benzamide;
In
diethyl ether;
for 1.5h;
Title compound not separated from byproducts;
Heating;
|
|
With
sodium tetrahydroborate;
In
methanol; tert-butyl alcohol;
for 2h;
Yield given. Yields of byproduct given;
|
|
With
LiPyrrBH3;
In
tetrahydrofuran;
at 0 ℃;
Yield given. Yields of byproduct given. Title compound not separated from byproducts;
|
|
With
LiPh2InH2;
In
diethyl ether;
for 24h;
Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Ambient temperature;
|
|
With
LiH-NICRA;
In
tetrahydrofuran;
for 24h;
|
92 % Chromat. 5 % Chromat. |
With
sodium tetrahydroborate; β‐cyclodextrin;
In
water;
at 20 ℃;
for 48h;
|
17 % Spectr. 66 % Spectr. |
With
LiPyrrBH3;
In
tetrahydrofuran; benzonitrile;
at 25 ℃;
for 6h;
|
|
With
borane N-ethyl-N-isopropylaniline complex;
In
tetrahydrofuran;
for 24h;
Title compound not separated from byproducts;
|
|
With
zinc(II) tetrahydroborate; silica gel;
In
tetrahydrofuran;
for 24h;
Yield given. Yields of byproduct given;
Ambient temperature;
|
|
With
2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; magnesium iodide;
In
toluene;
for 1h;
Yield given;
Heating;
|
|
With
sodium tetrahydroborate;
In
ethanol;
for 2h;
Yield given. Yields of byproduct given;
Heating;
|
|
With
i-Bu2Al-O-s-Bu; water; diisobutylaluminium hydride;
Yield given. Multistep reaction. Yields of byproduct given;
1) heptane, 25 deg C, 20 h;
|
|
With
(1-azabicyclo{2.2.2}octane)aluminium hydride;
In
toluene;
for 16h;
Yield given. Yields of byproduct given;
Ambient temperature;
|
|
With
LiPhInH3;
In
diethyl ether;
for 24h;
Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Ambient temperature;
|
|
With
zeolite supported zinc borohydride;
In
tetrahydrofuran;
at 20 ℃;
for 12h;
Yield given. Yields of byproduct given;
|
|
With
tert-butyl-N-methyl-N-isopropylamine-borane;
In
tetrahydrofuran;
at 20 ℃;
for 24h;
|
|
With
tricyclohexylphosphineindium trihydride;
In
toluene;
at -78 - 20 ℃;
for 15h;
|
44 % Spectr. 56 % Spectr. |
With
lithium aluminium tetrahydride; diethyl ether;
|
|
With
sodium tetrahydroborate;
In
water;
for 6h;
|
|
With
[1-(2-aminomethylphenyl)-3-methylimidazol-2-ylidene]-(η5-pentamethylcyclopentadienyl)(pyridine)ruthenium(II) hexafluorophosphate; potassium tert-butylate; hydrogen;
at 25 ℃;
for 3h;
under 6000.6 Torr;
|
ethylbenzene
1-Phenylethanol
2-phenylethanol
Conditions | Yield |
---|---|
bei elektrolytischer Oxydation;
|
|
With
lithium aluminium tetrahydride; Perbenzoic acid;
Mechanism;
Product distribution;
2.) ether, 30 min, reflux; study of the regioselectivity of autoxidation by reduction of the corresponding oxidation-mixture;
|
oxirane
phenyl sodium
benzene
diazomethane
(2-Hydroxyethyl)phenylethyl ether
2-phenethyloxy-tetrahydro-furan-2-carbonitrile
2-phenylethyl nicotinate
1-(2-((1-(ethyloxy)ethyl)oxy)ethyl)benzene
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