2-phenyl propionic acid
propionic acid, 2-phenyl-
Identification
| Name | 2-phenyl propionic acid |
| CAS Number | 492-37-5 |
| EINECS | 207-752-0 |
| FDA UNII | CH15E393A2 |
| Molecular Formula | C9 H10 O2 |
| Molecular Weight | 150.17710000 |
| MDL Number | MFCD00002650 |
| Nikkaji Number | J313.188B |
| Beilstein | 1863558 |
| CoE Number | 10164 |
| XlogP3 | 1.90 (est) |
Regulatory
| DG SANTE Food Flavourings | 08.108 2-phenylpropanoic acid |
Physical Properties
| Appearance | colorless to pale yellow clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 1.09400 to 1.10000 @ 25.00 °C. |
| Pounds per Gallon - (est). | 9.103 to 9.153 |
| Refractive Index | 1.51700 to 1.52300 @ 20.00 °C. |
| Melting Point | 16.00 to 21.00 °C. @ 760.00 mm Hg |
| Boiling Point | 144.00 to 147.00 °C. @ 11.00 mm Hg, 260.00 to 262.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.006000 mmHg @ 25.00 °C. (est) |
| Flash Point | 233.00 °F. TCC ( 111.67 °C. ) |
| logP (o/w) | 1.699 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for 2-phenyl propionic acid usage levels up to | not for fragrance use. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.0012 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 3200 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| Dairy products, excluding products of category 02.0 (01.0) | 3.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 2.00000 |
| Edible ices, including sherbet and sorbet (03.0) | 3.00000 |
| Processed fruit (04.1) | 2.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 10.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 5.00000 |
| Bakery wares (07.0) | 10.00000 |
| Meat and meat products, including poultry and game (08.0) | 2.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 2.00000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 5.00000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 10.00000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 3.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 10.00000 |
| Ready-to-eat savouries (15.0) | 15.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 5.00000 |
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Potential Uses
Natural Occurrence
Synonyms
benzeneacetic acid, a-methyl-
hydratropic acid
(±)-
hydratropic acid
hydratropic acid, (±)-isomer
alpha-
methyl benzene acetic acid
alpha-
methyl phenyl acetic acid
alpha-
methylbenzene acetic acid
(±)-a-
methylphenylacetic acid
2-
phenyl propanoic acid
alpha-
phenyl propionic acid
(±)-2-
phenylpropanoic acid
2-
phenylpropanoic acid
(±)-2-
phenylpropionic acid
2-
phenylpropionic acid
propionic acid, 2-phenyl-
PubMed:
Enantioseparation of chiral aromatic acids by multiple dual mode counter-current chromatography using hydroxypropyl-β-cyclodextrin as chiral selector.
PubMed:
Application and comparison of high performance liquid chromatography and high speed counter-current chromatography in enantioseparation of (±)-2-phenylpropionic acid.
PubMed:
Role of COX-2 in nonsteroidal anti-inflammatory drug enteropathy in rodents.
PubMed:
Oxidation of aliphatic, branched chain, and aromatic hydrocarbons by Nocardia cyriacigeorgica isolated from oil-polluted sand samples collected in the Saudi Arabian Desert.
PubMed:
Chiral carboxylic acids and their effects on melting-point behaviour in co-crystals with isonicotinamide.
PubMed:
pH-sensitive hydrogels of dextran: synthesis, characterization and in vivo studies.
PubMed:
Differential effects of fibrates on the metabolic activation of 2-phenylpropionic acid in rats.
PubMed:
Synthesis of enantiopure 2-aryl-2-methoxypropionic acids and determination of their absolute configurations by X-ray crystallography.
PubMed:
1-Benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2- phenylpropan-1-ones: Mosher-Bt reagents.
PubMed:
Asymmetric resolution in ester reduction by NaBH4 at the interface of aqueous aggregates of amino acid, peptide, and chiral-counterion-based cationic surfactants.
PubMed:
Hydrogels of dextran containing nonsteroidal anti-inflammatory drugs as pendant agents.
PubMed:
Parallel kinetic resolution of an oxazolidinone using a quasi-enantiomeric combination of [D,13C]-isotopomers of pentafluorophenyl 2-phenyl propionate.
PubMed:
Loading-washout studies of the stereoselective sinusoidal uptake of (R)- and (s)-2-phenylpropionyl acyl glucuronide.
PubMed:
Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using (S)-2-methoxy-2-(1-naphthyl)propionic acid.
PubMed:
Application of thin-layer chromatography to investigate oscillatory instability of the selected profen enantiomers in dichloromethane.
PubMed:
Stability and comparative metabolism of selected felbamate metabolites and postulated fluorofelbamate metabolites by postmitochondrial suspensions.
PubMed:
Sub- and supercritical chiral separation of racemic compounds on columns with stationary phases having different functional groups.
PubMed:
Formation of catechols via removal of acid side chains from ibuprofen and related aromatic acids.
PubMed:
Expression and purification of a recombinant enantioselective amidase.
PubMed:
Stereoselective hepatic disposition of model diastereomeric acyl glucuronides.
PubMed:
In vitro reactivity of carboxylic acid-CoA thioesters with glutathione.
PubMed:
Use of ionic liquids in a lipase-facilitated supported liquid membrane.
PubMed:
Covalent binding of 2-phenylpropionyl-S-acyl-CoA thioester to tissue proteins in vitro.
PubMed:
Self-micellization of gemfibrozil 1-O-beta acyl glucuronide in aqueous solution.
PubMed:
In vivo mechanistic studies on the metabolic activation of 2-phenylpropionic acid in rat.
PubMed:
Enantioselective covalent binding of 2-phenylpropionic Acid to protein in vitro in rat hepatocytes.
PubMed:
Studies on the chemical reactivity of 2-phenylpropionic acid 1-O-acyl glucuronide and S-acyl-CoA thioester metabolites.
PubMed:
Identification of degradation products of ibuprofen arising from oxidative and thermal treatments.
PubMed:
Enhancement of enzyme activity and enantioselectivity via cultivation in nitrile metabolism by Rhodococcus sp. CGMCC 0497.
PubMed:
Kinetics of intramolecular acyl migration of 1beta-O-acyl glucuronides of (R)- and (S)-2-phenylpropionic acids.
PubMed:
Metabolism and disposition of alpha-methylstyrene in rats.
PubMed:
Stereoselective internal acyl migration of 1beta-O-acyl glucuronides of enantiomeric 2-phenylpropionic acids.
PubMed:
The synthesis, in vitro reactivity, and evidence for formation in humans of 5-phenyl-1,3-oxazinane-2,4-dione, a metabolite of felbamate.
PubMed:
Quantification in patient urine samples of felbamate and three metabolites: acid carbamate and two mercapturic acids.
PubMed:
Dual effects of anti-inflammatory 2-arylpropionic acid derivatives on a major isoform of human liver 3alpha-hydroxysteroid dehydrogenase.
PubMed:
The stereo inversion of 2-arylpropionic acid non-steroidal anti-inflammatory drugs and structurally related compounds by Verticillium lecanii.
PubMed:
Evidence that multifunctional protein 2, and not multifunctional protein 1, is involved in the peroxisomal beta-oxidation of pristanic acid.
PubMed:
1-(5-Dimethylamino-1-naphthalenesulphonyl)-(S)-3-aminopyrrolidine (DNS-Apy) as a fluorescence chiral labelling reagent for carboxylic acid enantiomers.
PubMed:
Optimization of the chiral inversion of 2-phenylpropionic acid by Verticillium lecanii.
PubMed:
A mechanistic investigation of the microbial chiral inversion of 2-phenylpropionic acid by Verticillium lecanii.
PubMed:
Bi-directional chiral inversion of ketoprofen in CD-1 mice.
PubMed:
Synthesis and in vitro reactivity of 3-carbamoyl-2-phenylpropionaldehyde and 2-phenylpropenal: putative reactive metabolites of felbamate.
PubMed:
Involvement of arginine 120, glutamate 524, and tyrosine 355 in the binding of arachidonate and 2-phenylpropionic acid inhibitors to the cyclooxygenase active site of ovine prostaglandin endoperoxide H synthase-1.
PubMed:
Synthesis and enantioselectivity of the enantiomers of PG9 and SM21, new potent analgesic and cognition-enhancing drugs.
PubMed:
Presynaptic cholinergic modulators as potent cognition enhancers and analgesic drugs. 1. Tropic and 2-phenylpropionic acid esters.
PubMed:
Lack of stereoselectivity of the peroxisome proliferation induced by 2-phenylpropionic acid: evidence against a role for lipid disturbance in peroxisome proliferation.
PubMed:
The temperature dependence of steady-state kinetics: what can be learned about pig liver esterase stereospecificity?
PubMed:
Production of S-(+)-2-phenylpropionic acid from (R,S)-2-phenylpropionitrile by the combination of nitrile hydratase and stereoselective amidase in Rhodococcus equi TG328.
PubMed:
Isolation and identification of 3-carbamoyloxy-2-phenylpropionic acid as a major human urinary metabolite of felbamate.
PubMed:
Microbial metabolism of 2-arylpropionic acids: chiral inversion of ibuprofen and 2-phenylpropionic acid.
PubMed:
[Stereoselective chronopharmacokinetics of hydratropic acid in rats].
PubMed:
[The stereoselectivity of chrono-pharmacokinetic parameters of hydratropic acid in rats].
PubMed:
Glucuronidation of 3'-azido-3'-deoxythymidine in human liver microsomes: enzyme inhibition by drugs and steroid hormones.
PubMed:
Functional and immunochemical comparison of hepatic UDP-glucuronosyltransferases in a piscine and a mammalian species.
PubMed:
Formation of glycine conjugate and (-)-(R)-enantiomer from (+)-(S)-2-phenylpropionic acid suggesting the formation of the CoA thioester intermediate of (+)-(S)-enantiomer in dogs.
PubMed:
Purification, cloning, and primary structure of a new enantiomer-selective amidase from a Rhodococcus strain: structural evidence for a conserved genetic coupling with nitrile hydratase.
PubMed:
Determination of ibuprofen and its major metabolites in human urine by high-performance liquid chromatography.
PubMed:
Substrate specificity and enantioselectivity of arylcarboxylic acid glucuronidation.
PubMed:
[The inhibitory activities of 480156-S and its related compounds on prostaglandin synthetase].
PubMed:
Stereoselective metabolism of 2-phenylpropionic acid in rat. II. Studies on the organs responsible for the optical isomerization of 2-phenylpropionic acid in rat in vivo.
PubMed:
Stereoselective metabolism of 2-phenylpropionic acid in rat. I. In vitro studies on the stereoselective isomerization and glucuronidation of 2-phenylpropionic acid.
PubMed:
Stereospecificity of enzyme induction by 2-phenylpropionic acid.
PubMed:
The metabolic chiral inversion of 2-phenylpropionic acid in rat, mouse and rabbit.
PubMed:
Steric and electronic effects in the resolution of enantiomeric amides on a commercially available Pirkle-type high-performance liquid chromatographic chiral stationary phase.
PubMed:
Stereospecific induction of rat liver bilirubin UDPglucuronosyltransferase and lauric acid 12-hydroxylation by the isomers of 2-phenylpropionic acid.
PubMed:
Enantioselective disposition of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs. II. 2-Phenylpropionic acid protein binding.
PubMed:
Enantioselective disposition of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs. I. 2-Phenylpropionic acid disposition.
PubMed:
Application of a radial compression column to the high-performance liquid chromatographic separation of the enantiomers of some 2-arylpropionic acids as their diastereoisomeric s-(-)-1-(naphthen-1-yl)ethylamines.
PubMed:
Enantiospecific high-performance liquid chromatographic analysis of 2-phenylpropionic acid, ketoprofen and fenoprofen.
PubMed:
Structure-dependent induction of bilirubin glucuronidation and lauric acid 12-hydroxylation by arylcarboxylic acids chemically related to clofibrate.
PubMed:
Stereoselective disposition of hydratropic acid in rat.
PubMed:
High-performance liquid chromatographic separation of the enantiomers of anti-inflammatory 2-arylpropionates: suitability of the method for in vitro metabolic studies.
PubMed:
[In Process Citation].
PubMed:
The metabolic chiral inversion of 2-arylpropionic acids--a novel route with pharmacological consequences.
PubMed:
Absolute configuration of (-)anisodine (a new ganglio blocking agent) and (-)anisodinic acid.
PubMed:
Metabolism of arylacetic acids. 2. The fate of [14C]hydratropic acid and its variation with species.
PubMed:
Letter: Transition metal catalyzed asymmetric organic syntheses via polymer bound chiral ligands. Synthesis of R amino acids and hydratropic acid by hydrogenation.
PubMed:
[Preparation and study of phytotoxic activity of anilides of the (+/-) hydratropic acid].
PubMed:
Enzymatic inversion at saturated carbon: nature and mechanism of the inversion of R(-) p-iso-butyl hydratropic acid.
PubMed:
[A new anti-inflammatory agent: (3-benzoyl-2-phenylpropionic acid) (preliminary results)].
PubMed:
Studies in detoxication. 60. The metabolism of alkylbenzenes: isopropylbenzene (cumene) and derivatives of hydratropic acid.