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ALPHA-TOLUIC ACID

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

CAS Number: 122-79-2
EC Number: 204-575-0
IUPAC Name: phenyl acetate
Chemical Formula: C8H8O2

Other names: (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

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

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

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

Alpha-toluic acid is an acetate ester obtained by the formal condensation of phenol with acetic acid.
Alpha-toluic acid is a member of Alpha-toluic acids and a member of benzenes.
Alpha-toluic acid is functionally related to a phenol.

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

Alpha-toluic acid, 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.

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

Alpha-toluic acid, 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.

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

Molecular Weight: 136.15 g/mol
XLogP3: 1.5
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: 26.3Å²
Heavy Atom Count: 10
Complexity: 114
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Alpha-toluic acid:
Color: Colorless
Boiling Point: 195°C
Formula Weight: 136.15
Physical Form: Liquid

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

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

In humans, Alpha-toluic acid is involved in the Alpha-toluic acid metabolism.
Moreover, Alpha-toluic acid is found to be associated with kidney disease and phenylketonuria.

Alpha-toluic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound.
Alpha-toluic acid 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.

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

Alpha-toluic acid level in urine was used as a marker for the diagnosis of some forms of unipolar major depressive disorders.
Alpha-toluic acid 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.

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

Alpha-toluic acid 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 Alpha-toluic acid:
Alpha-toluic acid is used as a solvent, laboratory reagent, and in organic synthesis
Alpha-toluic acid is solvent, organic sythesis, laboratory reagent

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

Uses at industrial sites:
Alpha-toluic acid has an industrial use resulting in manufacture of another substance (use of intermediates).
Alpha-toluic acid is used for the manufacture of: chemicals.
Release to the environment of Alpha-toluic acid 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 Alpha-toluic acid:

Cellular Locations:
Cytoplasm
Extracellular

Handling and Storage of Alpha-toluic acid:

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 Alpha-toluic acid:

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:
Alpha-toluic acid 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 Alpha-toluic acid:

General advice:
Show Alpha-toluic acid 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 Alpha-toluic acid:

Unsuitable extinguishing media:
For Alpha-toluic acid no limitations of extinguishing agents are given.

Special hazards arising from Alpha-toluic acid 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 Alpha-toluic acid:

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 Alpha-toluic acid:

Personal protection:
Filter respirator for organic gases and vapours adapted to the airborne concentration of Alpha-toluic acid.
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 Alpha-toluic acid:
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.