HYDROXYACETOPHENONE

Hydroxyacetophenone is an aromatic fatty acid metabolite of phenylalanine with potential antineoplastic activity. 
Naturally occurring in mammals, Hydroxyacetophenone induces differentiation, growth inhibition, and apoptosis in tumor cells. 
Hydroxyacetophenone is an acetate ester obtained by the formal condensation of phenol with acetic acid. 

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

Hydroxyacetophenone is the ester of phenol and acetic acid. 
Hydroxyacetophenone can be produced by reacting phenol (Which can be produced by decarboxylation of aspirin)with acetic anhydride or acetyl chloride.

Hydroxyacetophenone can be separated into phenol and an acetate salt, via saponification: heating the Hydroxyacetophenone with a strong base, such as sodium hydroxide, will produce phenol and an acetate salt (sodium acetate, if sodium hydroxide were used).

Hydroxyacetophenone, also known as Phenylacetate, is an aromatic fatty acid metabolite of phenylalanine with potential antineoplastic activity. 
Naturally occurring in mammals, Hydroxyacetophenone induces differentiation, growth inhibition, and apoptosis in tumor cells. 

Hydroxyacetophenone mechanisms of action include decreased protein prenylation, activation of the peroxisome proliferation-activated receptors, inhibition of DNA methylation, and depletion of glutamine. 
Hydroxyacetophenone 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. 
Hydroxyacetophenone has a phenolic-like taste.

Hydroxyacetophenone is an acetate ester obtained by the formal condensation of phenol with acetic acid. 
Hydroxyacetophenone is a member of Hydroxyacetophenones and a member of benzenes. 
Hydroxyacetophenone is functionally related to a phenol.

Hydroxyacetophenone is a natural product found in Euglena gracilis and Arabidopsis thaliana with data available.
Hydroxyacetophenone is a metabolite found in or produced by Saccharomyces cerevisiae.

Hydroxyacetophenone, also known as (Acetyloxy)benzene, 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.

Hydroxyacetophenone is registered under the REACH Regulation but is not currently being manufactured in and / or imported to the European Economic Area.
Hydroxyacetophenone is used at industrial sites and in manufacturing.

Hydroxyacetophenone, also known as Phenylacetic acid or alpha-toluic acid, belongs to benzene and substituted derivatives class of compounds. 
Those are aromatic compounds containing one monocyclic ring system consisting of benzene. 

Hydroxyacetophenone is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 
Hydroxyacetophenone can be synthesized from acetic acid. 

Hydroxyacetophenone is also a parent compound for other transformation products, including but not limited to, hydratropic acid, 2,4,5-trihydroxyphenylacetic acid, and mandelamide. 
Hydroxyacetophenone 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 Hydroxyacetophenone a potential biomarker for the consumption of these food products. 

Hydroxyacetophenone can be found primarily in most biofluids, including cerebrospinal fluid (CSF), saliva, feces, and blood. 
Hydroxyacetophenone exists in all living species, ranging from bacteria to humans. 

In humans, Hydroxyacetophenone is involved in the Hydroxyacetophenone metabolism. 
Moreover, Hydroxyacetophenone is found to be associated with kidney disease and phenylketonuria. 

Hydroxyacetophenone is a non-carcinogenic (not listed by IARC) potentially toxic compound. 
Hydroxyacetophenone 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.

Hydroxyacetophenone is the ester of a phenol and acetic acid. 
Hydroxyacetophenone is a metabolite of anticancer drug phenylbutyrate (PB), natural neurotransmitter phenylethylamine. 
Naturally, Hydroxyacetophenone is an odorant found in strawberries, passion fruit, and black tea. 

Hydroxyacetophenone level in urine was used as a marker for the diagnosis of some forms of unipolar major depressive disorders. 
Hydroxyacetophenone 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.

Hydroxyacetophenone is an aromatic ester. 
Hydroxyacetophenone levels in urine are marker for the diagnosis of some forms of unipolar major depressive disorders.
Hydroxyacetophenone undergoes Fries rearrangement to form a mixture of o- and p-hydroxyacetophenones which are useful intermediates in manufacture of pharmaceuticals.

Hydroxyacetophenone 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 Hydroxyacetophenone:
Hydroxyacetophenone is used as a solvent, laboratory reagent, and in organic synthesis
Hydroxyacetophenone is solvent, organic sythesis, laboratory reagent

Hydroxyacetophenone is high-boiling aprotic solvent
Hydroxyacetophenone is used as a chemical intermediate for the synthesis of o-hydroxyacetophenone; p-hydroxyacetophenone; synephrine

Uses at industrial sites:
Hydroxyacetophenone has an industrial use resulting in manufacture of another substance (use of intermediates).
Hydroxyacetophenone is used for the manufacture of: chemicals.
Release to the environment of Hydroxyacetophenone can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).

Industry Uses:
Intermediates

Human Metabolite Information of Hydroxyacetophenone:

Cellular Locations:
Cytoplasm
Extracellular

Handling and Storage of Hydroxyacetophenone:

Precautions for safe handling:
measures against static discharge.

Hygiene measures:
Change contaminated clothing. 
Preventive skin protection recommended. 
Wash hands after working with substance.

Conditions for safe storage, including any incompatibilities:

Storage conditions:
Tightly closed.

Storage class:
Storage class (TRGS 510): 10: Combustible liquids

Stability and Reactivity of Hydroxyacetophenone:

Reactivity:
Forms explosive mixtures with air on intense heating.
A range from approx. 15 Kelvin below the flash point is to be rated as critical.

Chemical stability:
Hydroxyacetophenone is chemically stable under standard ambient conditions (room temperature).

Conditions to avoid:
Strong heating.

Incompatible materials:
Strong oxidizing agents, Strong acids, Strong bases, Strong reducing agents Strong oxidizing agents, Strong acids, Strong bases, Strong reducing agents

First Aid Measures of Hydroxyacetophenone:

General advice:
Show Hydroxyacetophenone safety data sheet to the doctor in attendance.

After inhalation:
Fresh air.

In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with water/ shower.

After eye contact:
Rinse out with plenty of water. 
Remove contact lenses.

After swallowing:
Immediately make victim drink water (two glasses at most). 
Consult a physician.

Firefighting Measures of Hydroxyacetophenone:

Unsuitable extinguishing media:
For Hydroxyacetophenone no limitations of extinguishing agents are given.

Special hazards arising from Hydroxyacetophenone or mixture:
Carbon oxides

Vapors are heavier than air and may spread along floors.
Forms explosive mixtures with air on intense heating.

Advice for firefighters:
In the event of fire, wear self-contained breathing apparatus.

Further information:
Remove container from danger zone and cool with water. 
Prevent fire extinguishing water
from contaminating surface water or the ground water system.

Accidental Release Measures of Hydroxyacetophenone:

Personal precautions, protective equipment and emergency procedures:

Advice for non-emergency personnel: 
Do not breathe vapors, aerosols. 
Avoid substance contact. 

Ensure adequate ventilation. 
Keep away from heat and sources of ignition.
Evacuate the danger area, observe emergency procedures, consult an expert.

Environmental precautions:
Do not let product enter drains.

Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 

Observe possible material restrictions.
Take up with liquid-absorbent material.

Dispose of properly. 
Clean up affected area.

Accidental Release Measures of Hydroxyacetophenone:

Personal protection:
Filter respirator for organic gases and vapours adapted to the airborne concentration of Hydroxyacetophenone. 
Collect leaking liquid in sealable containers. 

Absorb remaining liquid in sand or inert absorbent. 
Then store and dispose of according to local regulations.

Disposal Methods of Hydroxyacetophenone:
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.

Identifiers of Hydroxyacetophenone:
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 Hydroxyacetophenone:
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 Hydroxyacetophenone:
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 Hydroxyacetophenone:

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
(Acetyloxy)benzene
Acetoxybenzene

Other identifiers:
122-79-2