ACETYLPHENOL
Acetylphenol is an aromatic fatty acid metabolite of phenylalanine with potential antineoplastic activity, naturally occurring in mammals, and induces differentiation, growth inhibition, and apoptosis in tumor cells.
Acetylphenol is an acetate ester obtained by the formal condensation of phenol with acetic acid, characterized by a benzene ring with an acetyl group attached, and is used in the synthesis of dyes, pharmaceuticals, and fragrances.
Acetylphenol is a non-carcinogenic compound with a sweet, vanilla-like odor, found in various natural sources such as strawberries and black tea, and serves as a marker for some forms of unipolar major depressive disorders.
CAS Number: 122-79-2
EC Number: 204-575-0
Molecular Formula: C8H8O2
Molecular Weight (g/mol): 136.15
Synonyms: (Acetyloxy)benzene, 100843-EP2301983A1, 100843-EP2371831A1, 122-79-2, 355G9R500Y, 4-06-00-00613 (Beilstein Handbook Reference), A0043, ACETATE, PHENYL, Acetates, acetic acid phenyl, Acetic acid phenyl ester, Acetic acid, phenyl ester, ACETIC ACID, PHENYLESTER, Acetic acid,phenyl ester, Acetic acid-phenyl ester, Acetoxybenzene, Acetyl phenol, Acetylphenol, Actate de phnyle, AI3-01972, AKOS002710242, bmse000481, bmse010117, BRN 0636458, C00548, CHEBI:8082, CHEMBL289559, CS-0102517, CS-O-10949, D88203, DTXCID4030178, DTXSID3051626, EC 204-575-0, EINECS 204-575-0, FEMA 3958, FEMA NO. 3958, Fenylester kyseliny octove, Fenylester kyseliny octove [Czech], FT-0659102, FT-0673718, HSDB 2667, HY-128733, MFCD00008699, NCI60_002262, NSC 27795, NSC-27795, NSC27795, Phen-d5-ol, acetate, Phenol acetate, phenoxy ethan-1-one, PHENYL ACETATE, PHENYL ACETATE [FHFI], PHENYL ACETATE [HSDB], PHENYL ACETATE [MI], Phenyl acetate, 99%, Phenyl acetate, analytical standard, Phenyl ester of acetic acid, PhOAc, PIPERAZINECITRATEHYDRATE, PS-5400, Q419645, QY9, SCHEMBL35500, STK022563, UNII-355G9R500Y, W-109455, WLN: 1VOR, 2-Phenylacetate, Benzeneacetate, Benzeneacetic acid, ion(1-) [ACD/Index Name], BENZYLFORMATE, Phenylacetat [German] [ACD/IUPAC Name], Phenylacetate [ACD/IUPAC Name] [Wiki], Phénylacétate [French] [ACD/IUPAC Name], Phenylethanoate, w-Phenylacetate, ω-Phenylacetate, 103-82-2 [RN], 2-phenylethanoate, 3539899 [Beilstein], acetate, phenyl-, A-PHENYL-ACETATE, phenylacetate anion, phenylacetate(1-), phenylacetic acid anion, 122-79-2 [RN], 204-575-0 [EINECS], 355G9R500Y, 636458 [Beilstein], Acétate de phényle [French] [ACD/IUPAC Name], Acetic acid phenyl ester, Acetic acid, phenyl ester [ACD/Index Name], AJ2800000, MFCD00008699 [MDL number], Phenyl acetate [ACD/IUPAC Name] [Wiki], Phenyl-acetat [German] [ACD/IUPAC Name], (2,3,4,5,6-Pentadeuteriophenyl) acetate, [122-79-2] [RN], 1072946-32-7 [RN], 1072946-33-8 [RN], 122-84-9 [RN], 204-578-7 [EINECS], 22705-26-6 [RN], 2-Phenylacetate, 4-06-00-00613 [Beilstein], 4-06-00-00613 (Beilstein Handbook Reference) [Beilstein], 4-08-00-00460 [Beilstein], 4-13-00-00137 [Beilstein], 4'-Methoxyphenyl-2-propanone, Acetic acid phenyl ester; Phenyl ethanoate, Acetic acid, phenylester, Acetic acid-phenyl ester, Acetic acid-phenyl ester, Acetoxybenzene, Acetyl phenol, EINECS 204-575-0, FEMA 3958, Fenylester kyseliny octove, Fenylester kyseliny octove [Czech], MFCD03792523 [MDL number], o-Acetylphenol, PHENOL ACETATE, phenyl acetate on polystyrene, ca 4 mmol/g, PHENYL ACETATE|PHENYL ACETATE, Phenyl Acetate-d5, phenyl acetic acid, Phenyl ester of acetic acid, phenyl ethanoate, Phenylacetate [ACD/IUPAC Name] [Wiki], PS-5400, QY9, UNII:355G9R500Y, UNII-355G9R500Y, WLN: 1VOR
Acetylphenol is an aromatic fatty acid metabolite of phenylalanine with potential antineoplastic activity.
Naturally occurring in mammals, Acetylphenol induces differentiation, growth inhibition, and apoptosis in tumor cells.
Acetylphenol is an acetate ester obtained by the formal condensation of phenol with acetic acid.
Acetylphenol is an aromatic organic compound characterized by the presence of both an acetyl group (–COCH₃) and a phenolic ring.
Acetylphenol's chemical formula is C8H8O2, and it is structurally represented as a benzene ring with an acetyl group attached to one of the carbons in the ring.
Acetylphenol is a colorless to pale yellow liquid or crystalline solid with a distinctive sweet, vanilla-like odor.
Acetylphenol is synthesized through the acetylation of phenol using acetyl chloride or acetic anhydride in the presence of a catalyst such as aluminum chloride.
This reaction results in the introduction of the acetyl group into the phenol molecule, forming acetylphenol.
Acetylphenol is a member of the phenolic family and shares some properties with other phenolic compounds, including Acetylphenol's reactivity and utility in various chemical applications.
In the chemical industry, acetylphenol is valued for its role as an intermediate in the synthesis of a variety of other chemicals.
Acetylphenol is used in the manufacture of dyes, pharmaceuticals, and fragrances due to its ability to undergo further chemical transformations.
Additionally, acetylphenol serves as a key building block in the synthesis of polymer additives and stabilizers.
One notable application of acetylphenol is in the production of antioxidants used in the stabilization of polymers and plastics, where it helps prevent degradation caused by oxidative processes.
In the pharmaceutical industry, acetylphenol's derivatives are employed as active ingredients in certain medications, owing to their biological activity and efficacy.
Acetylphenol is also utilized in the creation of various flavoring and fragrance compounds.
Acetylphenol's pleasant aroma makes it a suitable ingredient in perfumes and as a flavoring agent in certain food products.
Despite its useful applications, acetylphenol should be handled with care due to its potential irritant properties and the need for proper safety precautions during its use and storage.
Overall, acetylphenol is an important compound with diverse applications across multiple industries, leveraging its chemical properties for the development of products ranging from industrial chemicals to consumer goods.
Acetylphenol is the ester of phenol and acetic acid.
Acetylphenol can be produced by reacting phenol (Which can be produced by decarboxylation of aspirin)with acetic anhydride or acetyl chloride.
Acetylphenol can be separated into phenol and an acetate salt, via saponification: heating the Acetylphenol with a strong base, such as sodium hydroxide, will produce phenol and an acetate salt (sodium acetate, if sodium hydroxide were used).
Acetylphenol is an aromatic fatty acid metabolite of phenylalanine with potential antineoplastic activity.
Naturally occurring in mammals, Acetylphenol induces differentiation, growth inhibition, and apoptosis in tumor cells.
Acetylphenol mechanisms of action include decreased protein prenylation, activation of the peroxisome proliferation-activated receptors, inhibition of DNA methylation, and depletion of glutamine.
Acetylphenol belongs to the class of organic compounds known as phenol esters.
These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
Acetylphenol has a phenolic-like taste.
Acetylphenol is an acetate ester obtained by the formal condensation of phenol with acetic acid.
Acetylphenol is a member of Acetylphenols and a member of benzenes.
Acetylphenol is functionally related to a phenol.
Acetylphenol is a natural product found in Euglena gracilis and Arabidopsis thaliana with data available.
Acetylphenol is a metabolite found in or produced by Saccharomyces cerevisiae.
Acetylphenol is the ester of acetic acid and phenol and used most often as a solvent.
Ungraded products supplied by Spectrum are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use.
Acetylphenol is registered under the REACH Regulation but is not currently being manufactured in and / or imported to the European Economic Area.
Acetylphenol is used at industrial sites and in manufacturing.
Acetylphenol, belongs to benzene and substituted derivatives class of compounds.
Those are aromatic compounds containing one monocyclic ring system consisting of benzene.
Acetylphenol is slightly soluble (in water) and a weakly acidic compound (based on its pKa).
Acetylphenol can be synthesized from acetic acid.
Acetylphenol is also a parent compound for other transformation products, including but not limited to, hydratropic acid, 2,4,5-trihydroxyphenylacetic acid, and mandelamide.
Acetylphenol is a sweet, civet, and floral tasting compound and can be found in a number of food items such as hyssop, cowpea, endive, and shea tree, which makes Acetylphenol a potential biomarker for the consumption of these food products.
Acetylphenol can be found primarily in most biofluids, including cerebrospinal fluid (CSF), saliva, feces, and blood.
Acetylphenol exists in all living species, ranging from bacteria to humans.
In humans, Acetylphenol is involved in the Acetylphenol metabolism.
Moreover, Acetylphenol is found to be associated with kidney disease and phenylketonuria.
Acetylphenol is a non-carcinogenic (not listed by IARC) potentially toxic compound.
Acetylphenol is a drug which is used for use as adjunctive therapy for the treatment of acute hyperammonemia and associated encephalopathy in patients with deficiencies in enzymes of the urea cycle.
Acetylphenol is the ester of a phenol and acetic acid.
Acetylphenol is a metabolite of anticancer drug phenylbutyrate (PB), natural neurotransmitter phenylethylamine.
Naturally, Acetylphenol is an odorant found in strawberries, passion fruit, and black tea.
Acetylphenol level in urine was used as a marker for the diagnosis of some forms of unipolar major depressive disorders.
Acetylphenol is used as a tool substrate to study esterase activity in the blood of patients in clinical studies of the effect of nutritional supplements on paraoxonase-1 levels.
Acetylphenol is an aromatic ester.
Acetylphenol levels in urine are marker for the diagnosis of some forms of unipolar major depressive disorders.
Acetylphenol undergoes Fries rearrangement to form a mixture of o- and p-hydroxyacetophenones which are useful intermediates in manufacture of pharmaceuticals.
Acetylphenol is produced from bacterial degradation of unabsorbed phenylalanine.
In health, beneficial intestinal bacteria produce some B-vitamins and provide stimulus for proper immune function.
However, if your stomach acid is not adequate, if you fail to digest protein, or if your diet does not supply sufficient fiber, the resulting overgrowth of unfavorable bacteria can release toxic products that your body must remove.
Uses of Acetylphenol:
Acetylphenol is used as a solvent, laboratory reagent, and in organic synthesis.
Acetylphenol is solvent, organic sythesis, laboratory reagent.
Acetylphenol is high-boiling aprotic solvent.
Acetylphenol is used as a chemical intermediate for the synthesis of o-hydroxyacetophenone; p-hydroxyacetophenone; synephrine.
Acetylphenol, an aromatic compound with the formula C₈H₈O₂, finds diverse applications across multiple industries due to its distinctive chemical properties.
As a key intermediate in organic synthesis, acetylphenol plays a crucial role in the manufacture of various chemicals, including pharmaceuticals, dyes, and polymer additives.
Acetylphenol's utility extends to the polymer industry, where it is used to produce stabilizers that enhance the longevity and performance of plastics by preventing oxidative degradation.
In the pharmaceutical sector, derivatives of acetylphenol are employed as active ingredients in medications and are studied for their potential biological activities, such as antimicrobial and antioxidant effects.
The fragrance and flavoring industries also benefit from acetylphenol's pleasant vanilla-like odor, incorporating it into perfumes, colognes, and certain food products to impart desirable scents and flavors.
Additionally, acetylphenol is used in the production of dyes and pigments, contributing to the development of colorants for textiles and other materials.
Acetylphenol's role as a chemical reagent in laboratory settings further highlights its versatility, making it an important compound in both industrial processes and consumer products.
Chemical Synthesis and Industry:
Intermediate in Organic Synthesis:
Acetylphenol serves as a key intermediate in the synthesis of other chemicals, including pharmaceuticals, dyes, and polymers.
Acetylphenol can undergo further reactions to produce derivatives with different functional groups, expanding its utility in chemical manufacturing.
Polymer Stabilizers:
Acetylphenol is used in the production of polymer additives and stabilizers.
Acetylphenol helps prevent oxidative degradation in plastics and other polymer materials, enhancing their longevity and performance.
Pharmaceutical Applications:
Active Pharmaceutical Ingredients:
Derivatives of acetylphenol are employed in the pharmaceutical industry as active ingredients in certain medications.
These derivatives can exhibit specific biological activities useful in therapeutic applications.
Pharmaceutical Research:
Acetylphenol and its derivatives are studied for their potential biological activities, including antimicrobial and antioxidant properties.
They can contribute to the development of new drugs and therapeutic agents.
Flavoring and Fragrance:
Fragrance Industry:
Acetylphenol is used in the fragrance industry due to its pleasant vanilla-like odor.
Acetylphenol is incorporated into perfumes and colognes to add a sweet, floral note.
Flavoring Agent:
In the food industry, acetylphenol's derivatives may be used as flavoring agents to impart specific tastes and aromas to food products.
Acetylphenol's sweet and vanilla-like scent makes it suitable for certain flavor applications.
Dyes and Pigments:
Acetylphenol is used in the production of dyes and pigments.
Acetylphenol's chemical structure allows it to be incorporated into various dye formulations, contributing to the development of colorants for textiles and other materials.
Analytical and Laboratory Use:
In laboratories, acetylphenol is utilized as a reagent in chemical analyses and experiments.
Acetylphenol can be used to test for the presence of other substances or as part of synthetic chemistry procedures.
Antioxidant Production:
Acetylphenol's derivatives are used to produce antioxidants that are added to industrial products, including fuels and lubricants, to prevent oxidation and degradation.
Uses at industrial sites:
Acetylphenol has an industrial use resulting in manufacture of another substance (use of intermediates).
Acetylphenol is used for the manufacture of: chemicals.
Release to the environment of Acetylphenol can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).
Industry Uses:
Intermediates
Benefits of Acetylphenol:
Chemical Synthesis:
Acts as a versatile intermediate in organic synthesis, facilitating the production of various chemicals, including pharmaceuticals and dyes.
Polymer Stabilizers:
Acetylphenol is used in creating stabilizers for polymers and plastics, enhancing their durability and resistance to oxidative degradation.
Pharmaceutical Applications:
Serves as an active ingredient or intermediate in drug development, contributing to therapeutic formulations.
Fragrance and Flavoring:
Valued for Acetylphenol's pleasant vanilla-like aroma, used in perfumes, colognes, and as a flavoring agent in food products.
Dyes and Pigments:
Utilized in the production of dyes and pigments, essential for coloring textiles and other materials.
Analytical Reagent:
Functions as a reagent in laboratory settings, aiding in chemical analyses and research.
Antioxidant Production:
Derivatives are used to produce antioxidants that prevent oxidation in industrial products like fuels and lubricants.
Handling and Storage of Acetylphenol:
Handling:
Use appropriate personal protective equipment (PPE) such as gloves, safety goggles, and lab coats to avoid skin and eye contact, as well as inhalation of vapors.
Handle acetylphenol in a well-ventilated area or under a fume hood to prevent inhalation of vapors.
Avoid eating, drinking, or smoking in areas where acetylphenol is handled.
Keep containers tightly closed when not in use to prevent contamination and evaporation.
Storage:
Store acetylphenol in a cool, dry place away from direct sunlight and sources of heat.
Use containers made of materials that are compatible with acetylphenol to prevent leaks or reactions.
Ensure that storage areas are well-ventilated to minimize the buildup of vapors.
Keep away from strong oxidizing agents, acids, and bases to avoid potential reactions.
Stability and Reactivity of Acetylphenol:
Stability:
Acetylphenol is generally stable under normal storage conditions.
Avoid exposure to extreme temperatures, strong acids, or bases to maintain stability.
Reactivity:
Reacts with strong oxidizing agents, which can lead to potential hazards.
Can be sensitive to strong acids and bases, which may cause degradation or unwanted reactions.
Avoid mixing with incompatible substances to prevent hazardous reactions.
First Aid Measures of Acetylphenol:
Inhalation:
Move the person to fresh air immediately.
Seek medical attention if symptoms such as coughing, difficulty breathing, or throat irritation persist.
Skin Contact:
Wash the affected area thoroughly with soap and water.
Remove contaminated clothing and footwear.
Seek medical attention if irritation, redness, or other symptoms persist.
Eye Contact:
Rinse eyes immediately with plenty of water for at least 15 minutes.
Seek medical attention if irritation persists or if vision problems occur.
Ingestion:
Rinse mouth with water.
Do not induce vomiting unless instructed by a medical professional.
Seek medical attention immediately.
Fire-Fighting Measures of Acetylphenol:
Extinguishing Media:
Use dry chemical powder, foam, or carbon dioxide (CO₂) to extinguish fires.
Water may be used cautiously, but ensure Acetylphenol is compatible with the fire situation.
Fire Fighting Instructions:
Wear self-contained breathing apparatus (SCBA) and protective clothing.
Cool containers exposed to fire with water to prevent rupture or explosion.
Avoid inhaling smoke or fumes; ensure adequate ventilation during and after the fire.
Accidental Release Measures of Acetylphenol:
Personal Precautions:
Evacuate the area if necessary and ensure that appropriate PPE is worn.
Avoid direct contact with spilled material and minimize dust or vapor generation.
Spill Containment:
Contain the spill using inert materials such as sand, earth, or vermiculite.
Collect the material using appropriate tools and place Acetylphenol into suitable waste disposal containers.
Cleanup:
Clean the affected area with soap and water, ensuring that residues are properly removed.
Dispose of waste according to local regulations and guidelines.
Exposure Controls/Personal Protective Equipment of Acetylphenol:
Exposure Limits:
Adhere to occupational exposure limits and guidelines established by regulatory agencies.
Engineering Controls:
Provide adequate ventilation in areas where acetylphenol is used or handled.
Use fume hoods or local exhaust systems to control airborne concentrations.
Personal Protective Equipment (PPE):
Respiratory Protection:
Use appropriate respiratory protection if ventilation is insufficient or if there is a risk of inhaling vapors.
Hand Protection:
Wear chemical-resistant gloves to protect against skin contact.
Eye Protection:
Use safety goggles or face shields to protect the eyes from splashes or vapors.
Body Protection:
Wear protective clothing to prevent skin contact, particularly if there is a risk of spills or splashes.
Identifiers of Acetylphenol:
CAS Number: 122-79-2
ChEBI: CHEBI:8082
ChemSpider: 28969
ECHA InfoCard: 100.004.160
PubChem CID: 31229
UNII: 355G9R500Y
CompTox Dashboard (EPA): DTXSID3051626
InChI: InChI=1S/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3
Key: IPBVNPXQWQGGJP-UHFFFAOYSA-N
InChI=1/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3
Key: IPBVNPXQWQGGJP-UHFFFAOYAF
SMILES: CC(=O)Oc1ccccc1
Synonym(s): Acetic acid phenyl ester
Linear Formula: CH3COOC6H5
CAS Number: 122-79-2
Molecular Weight: 136.15
Beilstein: 636458
EC Number: 204-575-0
MDL number: MFCD00008699
PubChem Substance ID: 24846821
NACRES: NA.22
CAS: 122-79-2
Molecular Formula: C8H8O2
Molecular Weight (g/mol): 136.15
MDL Number: MFCD00008699
InChI Key: IPBVNPXQWQGGJP-UHFFFAOYSA-N
PubChem CID: 31229
ChEBI: CHEBI:8082
IUPAC Name: phenyl acetate
SMILES: CC(=O)OC1=CC=CC=C1
Properties of Acetylphenol:
Chemical formula: C8H8O2
Molar mass: 136.150 g·mol−1
Density: 1.075 g/mL
Melting point: −30 °C (−22 °F; 243 K)
Boiling point: 195–196 °C (383–385 °F; 468–469 K)
Magnetic susceptibility (χ): -82.04·10−6 cm3/mol
Quality Level: 100
Assay: 99%
Refractive index: n20/D 1.501 (lit.)
bp: 196 °C (lit.)
Density: 1.073 g/mL at 25 °C (lit.)
SMILES string: CC(=O)Oc1ccccc1
InChI: 1S/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3
InChI key: IPBVNPXQWQGGJP-UHFFFAOYSA-N
Gene Information: human ... PON1(5444)
Molecular Weight: 136.15 g/mol
XLogP3: 1.5
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 2
Exact Mass: 136.052429494 g/mol
Monoisotopic Mass: 136.052429494 g/mol
Topological Polar Surface Area: 26.3Ų
Heavy Atom Count: 10
Complexity: 114
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Specifications of Acetylphenol:
Color: Colorless
Boiling Point: 195°C
Quantity: 25 g
Formula Weight: 136.15
Percent Purity: ≥98.0% (GC)
Physical Form: Liquid
Chemical Name or Material: Phenyl Acetate
Names of Acetylphenol:
Regulatory process names:
Phenyl acetate
phenyl acetate
IUPAC names:
Phenyl Acetate
Phenyl acetate
phenyl acetate
phenyl acetate
Preferred IUPAC name:
Phenyl acetate
Systematic IUPAC name:
Phenyl ethanoate
Other names:
Phenol acetate
Acetylphenol
Acetoxybenzene
Other identifiers:
122-79-2
