2-Phenylethanol

Cosmetic ingredients (Phenethyl Alcohol) -> CIR (Cosmetic Ingredient Review)

Deodorant

log Kow = 1.36

1.36

1.4

CHARACTERISTIC ROSE-LIKE ODOR

Pure PEA has an extremely mild roselike odor. >99% pure vary in odor because of the impurities present.

INITIALLY SLIGHTLY BITTER TASTE THEN SWEET & REMINISCENT OF PEACH

Sharp burning taste

1.0202 AT 20 °C/4 °C

1.02 g/cm³

1.017-1.020

7.58 centapoise @ 25 °C; 3.19 centpoise @ 50 °C

3.1 mm²/s at 50 °C

This chemical does not meet GHS hazard criteria for < 0.1% (2 of 2688) of reports.

Warning

H302 (81.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2688 reports by companies from 36 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Chemical: Benzeneethanol

Regulation (EC) No 1831/2003 (amended)

Benzeneethanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzeneethanol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 08-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13615

Benzeneethanol: Does not have an individual approval but may be used under an appropriate group standard

Higher alcohols are not highly toxic in the industrial setting; Can cause liver injury, somnolence, and respiratory depression in experimental animals; [HSDB] General anesthetic effect after subcutaneous injection of mice; [RTECS] A skin, eye, and respiratory tract irritant; Inhalation of high concentrations may cause CNS effects; Possible toxic effects on human reproduction; [ICSC] May cause corneal injury; [CHEMINFO] Safe when used as a flavoring agent in food; [JECFA] Has teratogenic effects in rats at doses >4.3 mg/kg; [REPROTOX] TLV Basis is embryo/fetal damage. [ACGIH TLVs and BEIs]

Phenethyl alcohol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.

1 - Materials that, under emergency conditions, can cause significant irritation.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

2-Phenylethanol

B: Compounds that form peroxides on concentration (distillation/evaporation)

2 samples had 10, 12 ppm, age &gt;1 yrs

Kelly

Acute Tox. 4 (81.5%)

Acute toxicity (ingestion) - category 4

Acute toxicity (Oral) - Category 4

Fresh air, rest. Refer for medical attention.

Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

TERRESTRIAL FATE: Based on a recommended classification scheme(2), an estimated Koc value of 29(SRC), derived from a molecular structure estimation method(1), suggests that 2-phenylethanol will have very high mobility in soil(SRC). 2-Phenylethanol is estimated to have a Koc of 29(1,SRC) and therefore would be expected to be very mobile in soil(2) and would be likely to leach. Limited data in an aerobic screening test(3) indicate that it is readily biodegradable and therefore may readily biodegrade in soil(SRC).

AQUATIC FATE: The Henry's Law constant for 2-phenylethanol estimated from its vapor pressure, 0.0868 mm Hg at 25 °C(1), and water solubility, 16,000 mg/L(2), is 1.5X10-7 atm-cu m/mol(SRC). Using this value of the Henry's Law constant, one can estimate a volatilization half-life of 2-phenylethanol in a model river 1 m deep flowing at 1 m/s with a wind speed of 3 m/s is 46.5 days(3,SRC). 2-Phenylethanol has been demonstrated to be readily biodegradable in an aerobic screening test(4) and therefore may biodegrade in natural water(SRC). Based on a recommended classification scheme(7), an estimated Koc value of 29(SRC), determined from molecular structure(5), indicates that 2-phenylethanol will not adsorb to sediment and particulate matter in the water column(SRC). An estimated BCF value of 6(SRC), based on a log Kow of 1.36(6) and a recommended regression-derived equation(3), suggest that 2-phenylethanol will not bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(8).

ATMOSPHERIC FATE: According to a theory of gas/particle partitioning of semivolatile organic compounds in the atmosphere(2), 2-phenylethanol, which has a vapor pressure of 0.0868 mm Hg at 25 °C(3) will exist as a vapor in the ambient atmosphere(SRC). Vapor-phase 2-phenylethanol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.6 days(1,SRC). 2-Phenylethanol solubility in water is 16,000 mg/L(4), and therefore it may be washed out of the atmosphere by rain(SRC).

2-Phenylethanol has been identified as a volatile component of following foods: tea(1), mushrooms(1), orange juice(2), beer (8-15 ppm)(2), Korean chamchwi(3), casava(4), filberts(5) and Kogyoku apples(6). It has also been identified in meat(7,8), blue cheese(9), a Swiss Mountain cheese(10) and wine(11).

On the basis of the available data, the Expert Panel concludes that Phenethyl Alcohol is safe in cosmetic products in the present practices of use at concentrations of up to 1%.

Safe for use in cosmetics, with qualifications

Cough. Sore throat. Headache. Nausea.

Redness.

Redness. Pain.

Abdominal pain. Burning sensation. Further see Inhalation.

In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, 2-phenylethanol was identified in discharges of the following industrial category (positive occurrences, median concn in ppb): timber products (5; 252.4), leather tanning (1; 140.1), iron and steel mfg (1; 18.7), nonferrous metals (2; 8.9), paint and ink (1; 37.7), organics and plastics (9; 31.1), textile mills (2; 14.9), pulp and paper (2; 44.3), rubber processing (1; 20.7), soaps and detergents (4; 182.1), pharmaceuticals (3; 301.2), explosives (1; 14.3), electronics (1; 176.2), synfuels (68; 262.4), publicly owned treatment works (10; 40.5), rum industry (10; 489.2)(1). Industries with maximum effluent concns above 1 ppm were: organics and plastics, 4.5 ppm; synfuels, 31.1 ppm, and the rum industry 4.6 ppm(1).

2-Phenylethanol has been reported in effluent from a publicly-owned treatment works (POTW) in New Jersey(1), the Iona Island wastewater treatment plant in Vancouver, British Colombia(2) and in leachate from a sanitary landfill in Barcelona, Spain(3). It was found in wastewater of a petrochemical company that discharged into the Calcasieu River, LA(4).

Using an estimation method based on molecular connectivity indices(1), the Koc for 2-phenylethanol is estimated to be 29(SRC). According to a suggested classification scheme(2), this Koc value suggests that 2-phenylethanol will have very high mobility in soil(SRC).

The effects of phenylethyl alcohol (PEA) on the pregnancy of female CrL: COBS CD (SD) BR strain rats (25/control and mid-dose groups, 35/low- and high-dose groups) exposed to PEA by skin painting at dose levels of 0 (water control), 0.14, 0.43 or 1.40 ml/kg/day during days 6-15 of pregnancy were evaluated. The animals were sacrificed on day 20 of pregnancy. Significant differences between high-dose level and control dams were observed in the following: increased clinical observations such as irritability, hunched posture, walking on toes, piloerection and peri-orbital staining, and increased mortality (3/35 animals), decreased body weight gain, decreased levels of creatinine, glutamic-pyruvic transaminase, and increased white cell count. Significant differences between high-dose level and control litter parameters were observed in the following: increased incidence of embryo-fetal deaths (primarily early in pregnancy), decrease in litter size and weight, increased incidence of defects including anophthalmia/microphthalmia, ventricular septal defects, defects/irregularities affecting thorax, and/or kinky tail, defects of the thoracic ribs and occurrence of cervical rib(s). No significant differences between treated and control animals were observed in the following: relative liver and kidney weights, or pregnancy rates. No significant differences between mid- and low-dose level and control groups were observed with respect to maternal toxicity or litter parameters, although a small, dose-dependent increase in some of the morphological parameters was observed in the fetuses of the mid-dose level group.

2-Phenylethanol is a natural product. It has been found in fresh tearose leaves(1). The alcohol, as well as a number of its esters, has been isolated from a great variety of natural sources including oranges, Plumeria acutifolia oil, Japanese tobacco leaf oil, yland-ylang, narcissus, hyacinth, lily, and tea leaves(2). Other natural essential oils containing 2-phenylethanol include: rose, carnation, Aleppo pine, orange blossom, geranium Bourbon, neroli and champaca(3).

/ALSO REPORTED FOUND/ IN TOBACCO... IT HAS BEEN IDENTIFIED IN WINES.

REPORTED FOUND (AS IS OR ESTERIFIED) IN SEVERAL NATURAL PRODUCTS: ROSE CONCRETE, ROSE ABSOLUTE (60% OR MORE), & ROSE DISTILLATION WATERS; ALSO FOUND IN ESSENTIAL OILS OF NEROLI, YLANG-YLANG, NARCISSUS, HYACINTH, LILY, TEA LEAVES, MICHELIA CHAMPACA, PANDAMUS ODORATISSIMUS, CONGO & REUNION GERANIUM...

PHENETHYL ALCOHOL 0.5% IN 0.9% SODIUM CHLORIDE APPLIED AS EYEDROPS TO PT IS REPORTED TO CAUSE SENSATION OF SMARTING IN ABOUT 3 OF 4 PT, BUT TO PRODUCE ONLY OCCASIONAL SLIGHT CONJUNCTIVAL HYPEREMIA.

... A patch test using phenyl ethyl alcohol full strength for 24 hr produced no irritation in 20 human subjects. A skin sensitization test carried out on 25 volunteers at a conc of 8% in petrolatum produced no sensitization reactions.

Similar threshold conc (0.5%) for conjunctival irritation were noted for phenethyl alcohol in humans and rabbits ... . /Phenethyl alcohol/

Phenethyl alcohol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.

2-PHENYLETHANOL YIELDS PHENYLACETYLALDEHYDE IN RABBITS: SMITH JM ET AL, BIOCHEM J, 56, 320, 1954. /FROM TABLE/

Phenylethyl alcohol is oxidized almost entirely to the corresponding acid. Metabolites excreted in urine following oral doses of 0.2 to 0.3 g/kg to rabbits were phenaceturic acid, the glycine conjugate of phenylacetic acid, 42%; glucosidurinic acid, 5%; and an ether-soluble acid, probably phenylacetic acid, 19%. Only 66% of the original dose could be accounted for. /Phenylethyl alcohol/

... beta-Phenylethyl alcohol is a substrate for ADH, with an initial rate of oxidation nearly as high as that of allyl alcohol and appreciably greater than that of ethanol.

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.

Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley&apos;s Condensed Chemical Dictionary, 11th ed)

Substances added to pharmaceutical preparations to protect them from chemical change or microbial action. They include ANTI-BACTERIAL AGENTS and antioxidants.

CIR ingredient: Phenethyl Alcohol

Found in many natural essential oils; [Merck Index] Used as a flavoring agent in foods and beverages; as a fragrance in perfumes, cosmetics, detergents, synthetic rose oils, and soaps; and as an antibacterial and preservative; [HSDB] Present in food at <20 ppm and in perfumes at 2%; [REPROTOX]

Using Disinfectants or Biocides [Category: Clean]

Used in flavors and perfumery (esp rose perfumes)

FRAGRANCE IN COSMETICS AND DETERGENTS; FLAVORING AGENT IN FOODS & BEVERAGES

Organic synthesis, synthetic rose oil, soaps, flavors, antibacterial, preservative.

(1977) 9.92X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1979) 1.01X10+8 GRAMS (PRINCPL CUSTMS DISTS)

2023: 10,000,000 - <25,000,000 lb

(1975) 4.54X10+8 G (CONSUMPTION AS FRAGRANCE)

(1976) 1.23X10+6 G (MIN CONSUMPTION IN FOODS)

For 1990, estimated total world production was 7000 tons, of which approximately one-fourth was used in North America. /PEA and its esters/

REACTION OF BENZENE, ETHYLENE OXIDE AND POWDERED ALUMINUM CHLORIDE; HYDROGENATION OF STYRENE OXIDE

BY REDUCTION OF ETHYL PHENYLACETATE WITH SODIUM IN ABSOLUTE ALCOHOL. BY HYDROGENATION OF PHENYLACETALDEHYDE IN PRESENCE OF NICKEL CATALYST.

Grignard synthesis: Chlorobenzene is converted to phenylmagnesium chloride which reacts with ethylene oxide at 100 °C to give beta-phenylethoxy magnesium chloride which is decomposed with sulfuric acid to give PEA.

Freidel-Craft process: Benzene is reacted with ethylene oxide over AlCl3.

Catalytic hydrogenation of styrene oxide.

GRADES: TECHNICAL; NF; FCC.

ASSAY 99% MIN.

Perfume-grade

EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants

Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

Benzeneethanol: ACTIVE

The Bouveault-Blanc Reduction method of synthesis in which phenylacetic ester is reduced with sodium and alcohol and Leonard's Method in which toluene is chlorinated to benzyl chloride which is then converted to phenylacetic ester, and then to PEA are primarily of historic interest.

Most of the 2-phenylethanol presently being manufactured is produced by the essentially one-step Friedel-Craft process, although the Grignard synthesis and catalytic hydrogenation of styrene oxide are presently used.

The Friedel-Craft method has been exhaustively studied to optimize reaction conditions and purification procedures. Because of the high reactivity of the intermediates and the tendency toward polymer formation, critical factors ... must be carefully balanced to provide an economical product with acceptable odor properties.

Most of the commercial product is satisfactorily purified using continuous vacuum fractionation. For highest purity, purification via the borate ester is required.