기본 정보
- 표준 SMILES
OCCOc1ccccc1- InChIKey
QCDWFXQBSFUVSP-UHFFFAOYSA-N- 분자식
- C8H10O2
- 평균 분자량
- 138.16 g/mol
개요
Ethylene glycol phenyl ether is a colorless liquid with a pleasant odor. Density 1.02 g / cm3. An irritant.
이름 및 식별자
- 우선 이름
- Phenoxyethanol
- IUPAC
- 2-phenoxyethanol
- 현지명
- 2-페녹시에탄올
- 영어명
- 2-Phenoxyethanol
- 분자식
- C8H10O2
- 분자량
- 138.16
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
122-99-6、9004-78-8- PubChem CID
- 31236
- ChEMBL
CHEMBL1229846- ChEBI
CHEBI:64275- UNII
- HIE492ZZ3T
- EC Number
- 204-589-7
- Nikkaji
- J5.360K
물성
구조 계산 물성
- XLogP
- 1.2
- 극성 표면적
- 29.5 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 10
- 형식 전하
- 0
- 복잡도
- 77.3
실험 및 물리화학적 성질
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
Cosmetics
Cosmetics ingredient -> Antioxidant; Base; Colorant; Fragrance; Other (Specify); Preservative/Stabilizer; Solvent
Cosmetic ingredients (Phenoxyethanol) -> CIR (Cosmetic Ingredient Review)
Preservative
LogP
log Kow = 1.16
1.160
1.2
1.16
Density
1.104 (USCG, 1999) - Denser than water; will sink
1.1094 at 20 °C/20 °C
Bulk density: 9.2 lb/gal
Relative density (water = 1): 1.1
1.11 @ 20°C
물리화학적 성질
- 녹는점
- 11 · 11-13 °C (lit.)
- 끓는 점
- 247 °C · 247 °C (lit.)
- 밀도
- 1.102 g/mL · 1.102 g/mL at 25 °C (lit.)
- 증기 밀도
- 4.8 · 4.8 (vs air)
- 증기압
- 0.01 mm · 0.01 mm Hg ( 20 °C)
- 굴절률
- 20 · n20/D 1.539
- FEMA
- 4620 · 4620 | 2-PHENOXYETHANOL
- 인화점
- 230 °F · >230 °F
- 저장 조건
- 30 °C · Store below +30°C.
- 용해도
- 가용성, 투명, 무색 내지 매우 희미한 노란색
- 산도 계수 (pKa)
- 14.36 · 14.36±0.10(Predicted)
- 물리적 상태
- 액체
- 색상
- 무색의
- Specific Gravity
- 1.109 · 1.109 (20/4℃)
- 냄새
- 희미한 방향족 냄새
- 수소이온지수(pH)
- 7 · 7 (10g/l, H2O, 23℃)
- 폭발한계
- 1.4 · 1.4-9.0%(V)
- 냄새 유형
- 꽃향기
- 수용성
- 30 g/L · 30g/L(20℃)
- Merck
- 14 · 14,7257
- BRN
- 1364011 · 1364011
- Henry's Law Constant
- 2.1 · 2.1×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- 주요 응용
- 환경
- 화장품 원료 기능
- 항균항균 방부제
- InChI
- 1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2
- InChIKey
- QCDWFXQBSFUVSP-UHFFFAOYSA-N
- SMILES
- OCCOc1ccccc1
- LogP
- 1.2 at · 1.2 at 23℃
- NIST
- 2 · 2-Phenoxyethanol(122-99-6)
- EPA
- Ethylene glycol monophenyl ether (122-99-6)
화학적 성질
clear colorless liquid
안전 및 규제
GHS 분류
GHS Classification
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P304+P340, P305+P354+P338, P317, P319, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 4299) of reports.
Danger
H302 (99.8%): Harmful if swallowed [Warning Acute toxicity, oral]
유해성 정보
Regulatory Information
Chemical: Ethanol, 2-phenoxy-
Hazard Traits - Respiratory Toxicity
Ethanol, 2-phenoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-phenoxy- 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: 29-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15160
2-Phenoxyethanol: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
This chemical is combustible. (NTP, 1992)
Combustible.
Hazards Summary
Can cause corneal injury; [CAMEO] A skin irritant that can have adverse effects on the central and peripheral nervous systems; [ICSC] Sensitization to this molecule is very rare. [Kanerva, p. 1825] No reproductive toxicity in animal studies, but liver and kidney injury occur at high doses. [MSDSonline] See Glycol Ethers.
The major hazards encountered in the use and handling of 2-phenoxyethanol stem from its toxicologic properties. Toxic by all routes (inhalation, ingestion, and dermal contact), exposure to this faintly aromatic, colorless, oily liquid may occur from its use as a fixative for cosmetics, perfumes, and soaps; as a bactericide and insect repellant; as a solvent for cellulose acetate,dyes, stamp pad, ball point, and specialty inks; as a chemical intermediate for carboxylic acid esters (eg, acrylate, maleate) and polymers (eg, formaldehyde, melamine); and as a preservative for human specimen used for dissection and demonstrations in anatomical studies. Effects from exposure may include eye irritation, headache, tremors, and CNS depression. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. 2-Phenoxyethanol must be preheated before ignition can occur. If this substance is involved in a fire, water spray gently applied to the surface will cause a frothing which will extinguish the fire.
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-Phenoxyethanol is included on this list.
안전 및 보호
Fire Fighting
Fire Extinguishing Agents: Water fog, carbon dioxide, dry chemical, alcohol foam. (USCG, 1999)
Use water spray, powder, alcohol-resistant foam, carbon dioxide.
First Aid Measures
Fresh air, rest.
Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
Spillage Disposal
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Preventive Measures
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
REASONABLE HANDLING PRECAUTIONS, PLUS PARTICULAR CARE TO PREVENT CONTACT WITH THE EYES, SHOULD PREVENT ANY SERIOUS TOXIC EFFECTS.
독성 정보
Ecotoxicity Values
EC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through bioassay with measured concentrations, 26.6 °C, dissolved oxygen 6.0 mg/L, hardness 45.0 mg/L calcium carbonate, alkalinity 42.0 mg/L calcium carbonate, and pH 7.62; Concentration: 344 mg/L for 96 hr (confidence limit 337-352 mg/L); Effect: loss of equilibrium
LC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through bioassay with measured concentrations, 26.6 °C, dissolved oxygen 6.0 mg/L, hardness 45.0 mg/L calcium carbonate, alkalinity 42.0 mg/L calcium carbonate, and pH 7.62; Concentration: 344 mg/L for 96 hr (confidence limit 337-352 mg/L)
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 15(SRC), determined from a structure estimation method(2), indicates that 2-phenoxyethanol is expected to have very high mobility in soil(SRC). Volatilization of 2-phenoxyethanol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.9X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 0.007 mm Hg at 25 °C(3), and water solubility, 2.6X10+4 mg/L(4). One biodegradation study reported theoretical 2-phenoxyethanol BODs of 2% (5-day), 71% (10-day), and 80% (20-day)(3); a theoretical 20-day BOD of 50%(3) indicates biodegrdaation may be an important environmnetal fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 15(SRC), determined from a structure estimation method(2), indicates that 2-phenoxyethanol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.007 mm Hg at 25 °C(4), and water solubility, 2.6X10+4 mg/L(5). According to a classification scheme(6), an estimated BCF of 1.5(SRC), from its log Kow of 1.16(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low. One biodegradation study reported theoretical 2-phenoxyethanol BODs of 2% (5-day), 71% (10-day), and 80% (20-day)(4); a theoretical 20-day BOD of 50% indicates a compound will largely be removed during biological waste treatment(4). 2-Phenoxyethanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-phenoxyethanol, which has a estimated vapor pressure of 0.007 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-phenoxyethanol 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 about 11.8 hours(SRC), calculated from its rate constant of 3.27X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Monitoring data have shown that 2-phenoxyethanol can be removed from the atmosphere via precipitation such as snow(4). 2-Phenoxyethanol does not absorb at wavelengths >290 nm(5), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Exposure Routes
The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
Dermal (A15201); ingestion
Toxicity Summary
Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
2-Phenoxyethanol is a glycol ether. Glycol ethers can produce toxicity following oxidation to the corresponding aldehyde and alkoxyacetic acid by alcohol dehydrogenase (ADH; EC 1.1.1.1) and aldehyde dehydrogenase (ALDH; EC 1.2.1.3), respectively. (A15201) 2-Phenoxyethanol causes reduction of NMDA-induced membrane currents, indicating a neurotoxic potential for 2-phenoxyethanol. (A15202)
Ecotoxicity Excerpts
/AQUATIC SPECIES/ PHENOXYETHANOL SHOWED A TOXIC EFFECT ON FERTILIZATION WHEN THE CONCN IN THE INSEMINATION DILUTENT WAS 0.05%. THIS EFFECT WAS LIMITED TO THE SPERM. THE ANESTHETIC DID NOT SEEM TO AFFECT THE EGG. THEREFORE, CAUTION SHOULD BE EXERCISED WHEN PHENOXYETHANOL IS USED TO IMMOBILIZE FISH DURING SPAWN TAKING.
/AQUATIC SPECIES/ 2-PHENOXYETHANOL (0.1-0.5 ML/L) SEDATED OR ANESTHETIZED FISH WITHIN MINUTES WHEN THE ANIMALS WERE IMMERSED IN THE AGENT. THE FISH RECOVERED RAPIDLY FOLLOWING REMOVAL FROM THE ANESTHETIC SOLN.
/AQUATIC SPECIES/ /Fathead Minnows were exposed to 2-Phenoxyethanol at nominal concentrations of 0, 68, 113, 188, 313, 522 mg/L for up to 96 hr./ Fish in the second highest concentration were immediately affected but began to respond to tap 12 hr. They did not school for the remainder of the test. Affected fish stopped schooling, became hypoactive on the tank bottom, then lost equilibrium prior to death.
/AQUATIC SPECIES/ THE APPROX TIMES TO 50% MORTALITY OF JUVENILE RAINBOW TROUT (SALMO GAIRDNERI) EXPOSED TO 2-PHENOXYETHANOL AT 0.75, 0.50, & 0.25 ML/L WERE 10.7 MINUTES, 26.3 MINUTES, & 3.7 HR, RESPECTIVELY. THE AVERAGE IMMOBILIZATION TIMES AT THE ABOVE 3 CONCN WERE 2, 3, & 4 MINUTES, RESPECTIVELY, & RECOVERY TIMES WERE APPROX 14, 9, & 6 MINUTES, RESPECTIVELY, FOR FISH THAT SURVIVED. 2-PHENOXYETHANOL THUS APPEARS TO BE A SUITABLE ANESTHETIC FOR JUVENILE SALMONIDS BUT ONLY FOR LIMITED DURATIONS, ESPECIALLY AT HIGHER CONCN.
Signs and Symptoms
Cough. Sore throat. Euphoria. Headache. Drowsiness. Slurred speech.
MAY BE ABSORBED! Redness. Dry skin. Numbness. Further see Inhalation.
Redness. Pain.
May cause vomiting and diarrhea.
Effluent Concentrations
2-Phenoxyethanol has been detected in wastewater effluents from the following industries: paint and ink, organics & plastics, photographic, and mechanical products(1). 2-Phenoxyethanol was detected in samples collected from oil reclaiming wastewaters(2). 2-Phenoxyethanol was qualitatively detected in wastewater samples collected from the Iona Island municipal treatment facility (British Columbia) in 1983(3).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-phenoxyethanol can be estimated to be 15(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-phenoxyethanol is expected to have very high mobility in soil.
TSCA Test Submissions
Teratogenicity was evaluated in pregnant New Zealand White rabbits (25/group) dermally exposed to 2-phenoxyethanol at treatment levels of 0, 300, 600, and 1000 mg/kg/day on gestation days (GD) 6-18. Surviving animals were sacrificed on GD 28. Significant differences were observed between treated and control animals in the following: slight to moderate reddening of the skin at the application site (all treated animals), maternal mortality with dead animals exhibiting dark-colored urine in the bladder, darkened kidneys, evidence of anorexia (hairball in stomach), superficial erosions, ulcers, and/or hemorrhages in the gastric mucosa, decreased feed and fecal material in the intestines, severely decreased red blood cell counts and packed cell volume, increased reticulocytes (evidence of a regenerative hemolytic anemia and the animals were jaundiced (high- and mid-dose groups). No significant differences were observed between treated and control animals in the following (mid- and low-dose groups unless otherwise noted): maternal body weights or weight gain, liver weights, pregnancy rates, resorptions, preimplantation losses, fetal sex ratio or body measurements, and incidence of fetal malformations or alterations in gross morphology, internal organs or skeletal system. No statistical evaluations were performed on the five high-dose group rabbits which survived until GD 28.
Human Toxicity Excerpts
/CASE REPORTS/ ... An 18-month-old boy who developed generalized eczema within 24 hr after administration of a DPT (diphtheria, pertussis, tetanus) vaccine. Patch tests with the individual components of the vaccine gave a positive result to PE 2% pet. ...
/CASE REPORTS/ ... A 53-year-old man with hand eczema caused by PE in an aqueous cream. Patch tests were positive to 1% PE, and the eczema improved with avoidance of the cream. ...
/CASE REPORTS/ A 24-year-old Asian woman suffered her first episode of acute urticaria 1 hr after eating papaya salad. Four days later, she again experienced generalized urticarial exanthema just after taking a shower, while applying a recently bought body lotion. She had never suffered from aquagenic or any other physical urticaria. She had no history of atopy or previous allergic reactions to food or drugs. ... Skin prick tests with common aeroallergens were all negative. The prick to prick test with fresh papaya was negative. Prick test with the body lotion gave a +++ reaction (Histamine: ++). In an open application test with the single ingredients of the body lotion and with papaya for 30 min we found a strong wheal reaction with pseudopods to PE. Tests with all the other ingredients and with papaya were negative. The prick test with Euxyl K 400 1% in pet. and with a dilution series of PE resulted in a ++ reaction to Euxyl K 400 and in a + reaction to 1% PE, +to 5% PE, and ++ to 10% PE. ... Observed an immediate reaction to PE with contact urticaria to a body lotion containing PE 1%. ...
/CASE REPORTS/ Peritonitis is the established term for infective inflammation of the peritoneum, whereas serositis generally refers to aseptic inflammation of a serous cavity, including the peritoneum. Serositis may be metabolic, viral, autoimmune, drug induced, genetic, allergic or granulomatous, or due to chemical antiseptics. In ... gynecological department, 4 patients had peritonitis and ascites after laparotomy. Based on the investigation...the solution used for peritoneal lavage (0.1% octenidine dihydrochloride and 2% phenoxyethanol) played a role in the tissue toxicity that caused chemical serositis with effusion.
For more Human Toxicity Excerpts (Complete) data for 2-PHENOXYETHANOL (8 total), please visit the HSDB record page.
규제 정보
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-Phenoxyethanol is included on this list.
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Ethylene glycol monophenyl ether is produced, as an intermediate or final product, by process units covered under this subpart.
안전 데이터
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- KM0350000
- 독성
- LD50 orally in Rabbit: 1850 mg/kg LD50 dermal Rabbit > 2000 mg/kg
- HS 번호
- 29094990
- risk_code
- 22-36-R36-R22
- hazard_code
- Xn,Xi
- safety_code
- 26-S26
- 기존화학 물질
- KE-28257
- 위험 참고 사항
- Irritant
- 자연 발화 온도
- 535 °C DIN 51794
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1STOT SE 3
- 스토리지 클래스
- 10 - Combustible liquids
- 유해 물질 데이터
- 122-99-6(Hazardous Substances Data)
화학 및 산업
약리 정보
Mechanism of Action
Phenoxyethanol has antibacterial properties and is effective against strains of Pseudomonas aeruginosa even in the presence of 20% serum. It not as effective against Proteus vulgaris, other gram-negative organisms, and gram-positive organisms. Phenoxyethanol has been used as a preservative at a concentration of 1%. A wider spectrum of antimicrobial activity is achieved with preservative mixtures of phenoxyethanol and hydroxybenzoates. Phenoxyethanol may be used as a 2.2% solution or a 2% cream for the treatment of superficial wounds, burns, or abscesses infected by Pseudomonas aeruginosa. In skin infection, derivatives of phenoxyethanol are used in combination with either cyclic acid or zinc undecenoate.
Metabolism/Metabolites
The fate of phenoxyethanol in rats and humans has been investigated. The rate of intestinal absorption was rapid, with 60-70% of the excreted (14)C detected at 3 hours and > 95% of the total 4-day urinary (14)C detected within the first 24 hr. Trace amounts of radioactivity were detected in feces. Four days after dosing, only trace amounts of radioactivity remained in the carcass, primarily in the liver (< 0.2% of the dose), fat and muscle. At the 4 day point, the (14)C concentration in blood was measured to be only 0.001. The major metabolite of phenoxyethanol is phenoxyacetic acid.
Once hydrolyzed, 2-phenoxyethanol is rapidly absorbed and oxidized to phenoxyacetic acid ...
YIELDS PHENOL IN CONIOPHORA, IN PLEUROTUS, & IN POLYSTICTUS ... . /FROM TABLE/
The toxicity of glycol ethers is associated with their oxidation to the corresponding aldehyde and alkoxyacetic acid by cytosolic alcohol dehydrogenase (ADH; EC 1.1.1.1.) and aldehyde dehydrogenase (ALDH; 1.2.1.3). Dermal exposure to these compounds can result in localised or systemic toxicity including skin sensitisation and irritancy, reproductive, developmental and hematological effects. It has previously been shown that skin has the capacity for local metabolism of applied chemicals. Therefore, there is a requirement to consider metabolism during dermal absorption of these compounds in risk assessment for humans. Cytosolic fractions were prepared from rat liver, and whole and dermatomed skin by differential centrifugation. Rat skin cytosolic fractions were also prepared following multiple dermal exposure to dexamethasone, ethanol or 2-butoxyethanol (2-BE). The rate of ethanol, 2-ethoxyethanol (2-EE), ethylene glycol, 2-phenoxyethanol (2-PE) and 2-BE conversion to alkoxyacetic acid by ADH/ALDH in these fractions was continuously monitored by UV spectrophotometry via the conversion of NAD+ to NADH at 340 nm. Rates of ADH oxidation by rat liver cytosol were greatest for ethanol followed by 2-EE >ethylene glycol >2-PE >2-BE. However, the order of metabolism changed to 2-BE >2-PE >ethylene glycol >2-EE >ethanol using whole and dermatomed rat skin cytosolic fractions, with approximately twice the specific activity in dermatomed skin cytosol relative to whole rat skin. This suggests that ADH and ALDH are localised in the epidermis that constitutes more of the protein in dermatomed skin than whole skin cytosol. Inhibition of ADH oxidation in rat liver cytosol by pyrazole was greatest for ethanol followed by 2-EE >ethylene glycol >2-PE >2-BE, but it only inhibited ethanol metabolism by 40% in skin cytosol. Disulfiram completely inhibited alcohol and glycol ether metabolism in the liver and skin cytosolic fractions. Although ADH1, ADH2 and ADH3 are expressed at the protein level in rat liver, only ADH1 and ADH2 are selectively inhibited by pyrazole and they constitute the predominant isoforms that metabolise short-chain alcohols in preference to intermediate chain-length alcohols. However, ADH1, ADH3 and ADH4 predominate in rat skin, demonstrate different sensitivities to pyrazole, and are responsible for metabolising glycol ethers. ALDH1 is the predominant isoform in rat liver and skin cytosolic fractions that is selectively inhibited by disulfiram and responds to the amount of aldehyde formed by the ADH isoforms expressed in these tissues. Thus, the different affinity of ADH and ALDH for alcohols and glycol ethers of different carbon-chain length may reflect the relative isoform expression in rat liver and skin. Following multiple topical exposure, ethanol metabolism increased the most following ethanol treatment, and 2-BE metabolism increased the most following 2-BE treatment. Ethanol and 2-BE may induce specific ADH and ALDH isoforms that preferentially metabolise short-chain alcohols (i.e. ADH1, ALDH1) and longer chain alcohols (i.e. ADH3, ADH4, ALDH1), respectively. Treatment with a general inducing agent such as dexamethasone enhanced ethanol and 2-BE metabolism suggesting induction of multiple ADH isoforms.
Studies were conducted... to evaluate the in vitro hemolytic potential of / ethylene glycol phenyl ether/ EGPE and its major metabolite using rabbit red blood cells (RBC). Phenoxyacetic acid (PAA) was identified as a major blood metabolite of EGPE. In vitro exposure of female rabbit erythrocytes indicated EGPE to be considerably more hemolytic than PAA.
Oxidized to the corresponding aldehyde and alkoxyacetic acid by alcohol dehydrogenase (ADH; EC 1.1.1.1) and aldehyde dehydrogenase (ALDH; EC 1.2.1.3), respectively. (A15201)
MeSH Pharmacological Classification
Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain. They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site.
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.
Absorption, Distribution and Excretion
The fate of phenoxyethanol in rats and humans has been investigated. More than 90% of an oral dose of 16, 27 or 160 mg/kg body weight of (2-(14)C)phenoxyethanol administered to male Colworth rats by was excreted in the urine within 24 hours of administration. A female rat also excreted about 90% of a dose of 27 mg/kg body weight in the urine within 24 hours. About 2% and 1.3% of the ingested dose was recovered from the exhaled air of female and male rats, respectively.
A pharmacokinetic study of phenoxyethanol was performed using a mass spectrometry model for simultaneous analysis of phenoxyethanol (PE) and its major metabolite, phenoxyacetic acid (PAA), in rat plasma, urine, and 7 different tissues. The absolute topical bioavailability of PE was 75.4% and 76.0% for emulsion and lotion, respectively. Conversion of PE to PAA was extensive, with the average AUCPAA-to-AUCPE ratio being 4.4 and 5.3 for emulsion and lotion, respectively. The steady-state tissue-to-plasma PE concentration ratio (Kp) was higher than unity for kidney, spleen, heart, brain, and testis and was lower (0.6) for lung and liver, while the metabolite Kp ratio was higher than unity for kidney, liver, lung, and testis and was lower (0.3) for other tissues.
... An entire oral dose of 11 mg of unlabelled 2-phenoxyethanol was accounted for in the urine of one healthy male volunteer as 2-phenoxyacetic acid. Most of the acid was excreted unconjugated.
The fate of 2-phenoxyethanol in rats and humans has been investigated. More than 90% of an oral dose of 16, 27 or 160 mg/kg bw of (2-(14)C)phenoxyethanol given to male Colworth rats by gavage was excreted in the urine within 24 hr. A female rat also excreted about 90% of a dose of 27 mg/kg bw in the urine within 24 hr. Approximately 2 and 1.3% of the ingested dose was recovered from expired air of female and male rats, respectively. The rate of intestinal absorption was rapid, with 60-70% of the excreted (14)C detected at 3 hr and > 95% of the total 4-day urinary (14)C detected within the first 24 hr. Trace amounts of radioactivity were detected in feces. Four days after dosing, only trace amounts of radioactivity remained in the carcass, primarily in the liver (< 0.2% of the dose), fat and muscle. At 4 days, the (14)C concentration in blood was only 0.001.
... NOT READILY ABSORBED THROUGH THE SKIN IN ACUTELY TOXIC AMT.
2-PHENOXYETHANOL (0.1-0.5 ML/L) SEDATED OR ANESTHETIZED FISH WITHIN MINUTES WHEN THE ANIMALS WERE IMMERSED IN THE AGENT. WHEN ADMIN IN THIS WAY, THE ANESTHETIC WAS ABSORBED INTO THE BLOOD STREAM THROUGH THE GILL LAMELLAE.
용도 및 제조
Uses
CIR ingredient: Phenoxyethanol
Used in perfumes, insect repellants, and antiseptics and to produce other organic chemicals; [Merck Index, 7257] Used as a solvent for inks, dyes, and cleaners; [HSDB]
Metal Degreasing [Category: Clean]
Fixative for perfumes, in organic synthesis; as a bactericide in conjunction with quaternary ammonium compounds
Solvent for cellulose acetate, dyes; inks, resins; perfume fixative; bactericidal agent; organic synthesis of plasticizers, germicides, pharmaceuticals; insect repellents
MEDICATION
U.S. Production
2023: 25,000,000 - <40,000,000 lb
(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS
(1981) PROBABLY GREATER THAN 4.54X10+6 GRAMS
Ethanol, 2-phenoxy- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5451]
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Ethanol, 2-phenoxy-. Aggregated National Production Volume: 10 to < 50 million pounds.
Methods of Manufacturing
A mixture of ethylene chlorohydrin in 30% aqueous NaOH may be added to phenol at 100-110 °C to give 2-phenoxyethanol in 98% yield.
Obtained by treating phenol with ethylene oxide in an alkaline medium.
Produced by the hydroxyethylation of phenol ... in the presence of alkali-metal hydroxides or alkali metal borohydrides.
Household Products
Cosmetics product ingredient: 2-Phenoxyethanol
Information on 734 consumer products that contain 2-Phenoxyethanol in the following categories is provided:
Use Classification
EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants;Solvents
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
Cosmetics -> Preservative
General Manufacturing Information
Paint and Coating Manufacturing
Ethanol, 2-phenoxy-: ACTIVE
응용 분야
개요Phenoxyethanol is an organic chemical compound, a glycol ether often used in dermatological products such as skin creams and sunscreen. It is a colorless oily liquid. It is a bactericide (usually used in conjunction with quaternary ammonium compounds). Phenoxyethanol is used in many applications such as cosmetics, vaccines and pharmaceuticals as a preservative.
용도Phenoxyethanol is a preservative used in consumer and health care products, including vaccines, pen inks, ear drops, shampoos, skin cleansers, moisturizers, sun care products, and topical medicaments. The preservative Euxyl-K 400 also contains 2-phenoxyethanol, in combination with methyldibromoglutaronitrile. Phenoxyethanol is commonly used in cosmetics for its antibacterial and antifungal properties. It is increasingly being used in vaccines as a substitute for thiomersal and is also a component of pen inks and, more rarely, ear drops.Reactions to phenoxyethanol have rarely been reported. Three cases of CoU induced by phenoxyethanol in cosmetics have been reported.2-Phenoxyethanol is used as a single agent and in combination with other preservatives such as 1,2-dibromo-2,4-dicyanobutane (Euxyl K 400) and parabens, or in conjunction with quaternary ammonium compounds.The possibility of immunological IgE-mediated reaction could not be confirmed because specific IgE against 2-phenoxyethanol was negative.
일반 설명Colorless liquid with a pleasant odor. Density 1.02 g / cm3. An irritant.
제조 방법
생산 방법Phenoxyethanol is prepared by treating phenol with ethylene oxide in an alkaline medium.
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