2-phenyl propionic acid

propionic acid, 2-phenyl-

CAS: 492-37-5 C9 H10 O2 MW: 150.17710000

Identification

Name2-phenyl propionic acid
CAS Number492-37-5
EINECS207-752-0
FDA UNIICH15E393A2
Molecular FormulaC9 H10 O2
Molecular Weight150.17710000
MDL NumberMFCD00002650
Nikkaji NumberJ313.188B
Beilstein1863558
CoE Number10164
XlogP31.90 (est)

Regulatory

DG SANTE Food Flavourings08.108 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 SDSView
European informationMost important hazard(s):
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavoring agents
Recommendation for 2-phenyl propionic acid usage levels up tonot 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 Concern1800 (μg/person/day)
Structure ClassI
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

None Found

Natural Occurrence

not found in nature

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.