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2-phenyl propionic acid
propionic acid, 2-phenyl-

Supplier Sponsors

CAS Number: 492-37-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-752-0
FDA UNII: CH15E393A2
Nikkaji Web:J313.188B
Beilstein Number:1863558
MDL:MFCD00002650
CoE Number:10164
XlogP3:1.90 (est)
Molecular Weight:150.17710000
Formula:C9 H10 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
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
Boiling Point: 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
 water, 4987 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
(+/-)-2-Phenylpropionic Acid
EMD Millipore
For experimental / research use only.
2-Phenylpropionic Acid
sds
Frinton Laboratories
For experimental / research use only.
2-Phenylpropionic Acid
Penta International
2-PHENYLPROPIONIC ACID
Sigma-Aldrich: Aldrich
For experimental / research use only.
2-Phenylpropionic acid 97%
sds
TCI AMERICA
For experimental / research use only.
DL-2-Phenylpropionic Acid >98.0%(GC)(T)
sds
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 3.0000015.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 2.0000010.00000
Edible ices, including sherbet and sorbet (03.0): 3.0000015.00000
Processed fruit (04.1): 2.0000010.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000050.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 10.0000050.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.0000010.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 3.0000015.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000050.00000
Ready-to-eat savouries (15.0): 15.0000075.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000
 
Safety References:
European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 14, Revision 1 (FGE.14Rev1): Phenethyl alcohol, aldehyde, acetals, carboxylic acid and related esters from chemical group 15 and 22 [1] - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 53, Revision 1 (FGE.53Rev1): Consideration of phenethyl alcohol, aldehyde, acid and related acetals and esters evaluated by JECFA (59th meeting) FGE.23Rev1 (2008)
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):492-37-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10296
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-phenylpropanoic acid
Chemidplus:0000492375
 
References:
 2-phenylpropanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10296
Pubchem (sid):134976645
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB11743
FooDB:FDB028418
Export Tariff Code:2916.39.7900
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 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-
 

Articles:

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.
 
Notes:
2-Phenylpropionate is an intermediate in alpha-Methylstyrene (2-phenylpropylene) metabolism. It was identified in human liver slices in small amounts. It is likely that 2-Phenylpropionate derives from 2-phenylpropionaldehyde, formed from a 1,2-hydride shift during the transfer of active oxygen to the vinyl group, as has been proposed for the cytochrome P450-mediated oxidation of styrene to form phenylacetaldehyde. (PMID: 11159807) [HMDB]
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