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Chemistry

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Also known as: 2-phenylacetic acid, Benzeneacetic acid, 103-82-2, Phenylethanoic acid, Alpha-toluic acid, Acetic acid, phenyl-
Molecular Formula
C8H8O2
Molecular Weight
136.15  g/mol
InChI Key
WLJVXDMOQOGPHL-UHFFFAOYSA-N
FDA UNII
ER5I1W795A

Phenylacetic Acid
Phenylacetic acid is a metabolite found in or produced by Saccharomyces cerevisiae.
Phenylacetic acid is a Nitrogen Binding Agent. The mechanism of action of phenylacetic acid is as an Ammonium Ion Binding Activity.
1 2D Structure

Phenylacetic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-phenylacetic acid
2.1.2 InChI
InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
2.1.3 InChI Key
WLJVXDMOQOGPHL-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)CC(=O)O
2.2 Other Identifiers
2.2.1 UNII
ER5I1W795A
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Phenylacetate

2. Phenylacetic Acid, Ammonium Salt

3. Phenylacetic Acid, Calcium Salt

4. Phenylacetic Acid, Cesium Salt

5. Phenylacetic Acid, Lithium Salt

6. Phenylacetic Acid, Mercury Salt

7. Phenylacetic Acid, Potassium Salt

8. Phenylacetic Acid, Rubidium Salt

9. Phenylacetic Acid, Sodium Salt

10. Phenylacetic Acid, Sodium Salt , Carboxy-(11)c-labeled Cpd

11. Sodium Phenylacetate

2.3.2 Depositor-Supplied Synonyms

1. 2-phenylacetic Acid

2. Benzeneacetic Acid

3. 103-82-2

4. Phenylethanoic Acid

5. Alpha-toluic Acid

6. Acetic Acid, Phenyl-

7. Phenylacetate

8. Benzenacetic Acid

9. Benzylformic Acid

10. Phenyllacetic Acid

11. Benzylcarboxylic Acid

12. Phenyl Acetic Acid

13. Kyselina Fenyloctova

14. Phenylacetic Acid (natural)

15. .alpha.-toluic Acid

16. Kyselina Fenyloctova [czech]

17. Omega-phenylacetic Acid

18. Fema No. 2878

19. .omega.-phenylacetic Acid

20. Nsc 125718

21. Brn 1099647

22. Chebi:30745

23. Ai3-08920

24. Phenyl-acetic Acid

25. Chembl1044

26. Er5i1w795a

27. Benzeneacetate

28. Mfcd00004313

29. Nsc125718

30. Nsc-125718

31. Ncgc00159477-02

32. 51146-16-8

33. Dsstox_cid_1656

34. Dsstox_rid_76268

35. Dsstox_gsid_21656

36. 1173020-54-6

37. 17303-65-0

38. Cas-103-82-2

39. Hsdb 5010

40. Einecs 203-148-6

41. Unii-er5i1w795a

42. Phenylacetic

43. Phenylethanoate

44. Phenylessigsaure

45. W-phenylacetate

46. Alpha-toluate

47. Phenylactic Acid

48. A-toluate

49. A-toluic Acid

50. Benzeneacetiic Acid

51. Omega-phenylacetate

52. Organic White Solid

53. W-phenylacetic Acid

54. Phenylacetate, Xix

55. 2-phenyl-acetic Acid

56. Phenylacetic Acid, 99%

57. Bmse000220

58. Epitope Id:116202

59. Ec 203-148-6

60. Schembl1459

61. 4-09-00-01614 (beilstein Handbook Reference)

62. Phenyl-[13c6]-acetic Acid

63. Phenylacetic Acid [mi]

64. Phenylacetic Acid [fcc]

65. Dtxsid2021656

66. Phenylacetic Acid [fhfi]

67. Phenylacetic Acid [hsdb]

68. Bdbm16419

69. Zinc388462

70. Phenylacetic Acid_gurudeebansatyavani

71. Tox21_113042

72. Tox21_200533

73. Nsc139637

74. Phenylacetic Acid, Natural, >=99%

75. Stk297835

76. Phenylacetic Acid, Analytical Standard

77. Akos000291351

78. Tox21_113042_1

79. Db09269

80. Dl-0063

81. Nsc-139637

82. Phenylacetic Acid, >=99%, Fcc, Fg

83. Ncgc00159477-03

84. Ncgc00159477-05

85. Ncgc00258087-01

86. Bp-11383

87. Nci60_000596

88. Nci60_002571

89. Phenylacetic Acid, Natural, >=99%, Fg

90. Astugenal Component Phenylacetic Acid

91. Db-003759

92. Db-055176

93. Ft-0641197

94. Ft-0701063

95. Phenylacetic Acid, Plant Cell Culture Tested

96. Tropicamide Impurity D [ep Impurity]

97. C07086

98. Tropicamide Related Compound D [usp-rs]

99. Q410842

100. Tropicamide Related Compound D [usp Impurity]

101. Antineoplaston As 2-1 Component Phenylacetic Acid

102. Antineoplaston As2-1 Component Phenylacetic Acid

103. Benzylpenicillin Sodium Impurity B [ep Impurity]

104. Benzylpenicillin Potassium Impurity B [ep Impurity]

105. Procaine Benzylpenicillin Impurity E [ep Impurity]

106. 8727557e-aa75-49e9-8e5a-7a2412d71888

107. Tropicamide Related Compound D, United States Pharmacopeia (usp) Reference Standard

108. Tropicamide Impurity D (phenylacetic Acid - Drug Precursor), European Pharmacopoeia (ep) Reference Standard

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 136.15 g/mol
Molecular Formula C8H8O2
XLogP31.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass136.052429494 g/mol
Monoisotopic Mass136.052429494 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count10
Formal Charge0
Complexity114
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For use as adjunctive therapy for the treatment of acute hyperammonemia and associated encephalopathy in patients with deficiencies in enzymes of the urea cycle.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antimetabolites, Antineoplastic

Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
PHENYLACETIC ACID
5.2.2 FDA UNII
ER5I1W795A
5.2.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - Nitrogen Binding Agent
5.3 Absorption, Distribution and Excretion

Volume of Distribution

19.2 3.3 L.


... Although exhaled volatile organic compound (VOC) patterns change in obstructive sleep apnea (OSA) patients, individual VOC profiles are not fully determined. The primary outcome was VOC characterizations; secondary outcomes included their relationships with sleep and clinical parameters in OSA patients. We prospectively examined 32 OSA patients with an apnea-hypopnea index (AHI) >/= 15 by full polysomnography, and 33 age- and sex-matched controls without obvious OSA symptoms. Nine severe OSA patients were examined before and after continuous positive airway pressure (CPAP) treatment. By applying a method which eliminates environmental VOC influences, exhaled VOCs were identified by gas chromatography (GC)-mass spectrometry, and their concentrations were determined by GC. Exhaled aromatic hydrocarbon concentrations (toluene, ethylbenzene, p-xylene, and phenylacetic acid) in the severe OSA groups (AHI >/= 30) and exhaled saturated hydrocarbon concentrations (hexane, heptane, octane, nonane, and decane) in the most severe OSA group (AHI >/= 60) were higher than those in the control group. Exhaled isoprene concentrations were increased in all OSA groups (AHI >/= 15); acetone concentration was increased in the most severe OSA group. Ethylbenzene, p-xylene, phenylacetic acid, and nonane concentrations were increased according to OSA severity, and correlated with AHI, arousal index, and duration of percutaneous oxygen saturation (SpO2)

PMID:28003437 Aoki T et al; Toxicol Sci 156 (2): 362-374 (2017)


The dose limiting toxicity and pharmacokinetics of phenylacetic acid (phenylacetate) were studied in 17 patients with advanced solid tumors who received single iv bolus doses followed by a 14 day continuous iv infusion of the drug in a phase I trial. Phenylacetic acid displayed nonlinear pharmacokinetics with evidence for induction of drug clearance. Ninety-nine percent of phenylacetic acid elimination was accounted for by conversion to phenylacetylglutamine which was excreted in the urine...

PMID:8137283 Thibault A et al; Cancer Res 54: 1690-94 (1994)


Phenylacetic acid... /is/ rapidly absorbed from human buccal tissues or membranes.

National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 754


Man excreted 93%...as glutamine conjugate... . New world monkeys excreted conjugates of glutamine, glycine and taurine, while old world species excreted large proportion of free acid and only glutamine and taurine conjugates. Non-primate species excreted only glycine connjugate.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 569


Distribution of conjugates in 24 hr urine samples showed marked species variation.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 569


5.4 Metabolism/Metabolites

Phenylacetate esterases found in the human liver cytosol. Human plasma esterase also hydrolyze phenylacetate. Phenylacetate hydrolysis involved arylesterase in plasma, both arylesterase and carboxylesterase in liver microsomes and carboxylesterase in liver cytosol. Plasma hydrolysis is less important and overall esterase activity is lower in humans than in the rat.


Although there has been increasing interest in the use of high protein diets, little is known about dietary protein related changes in the mammalian metabolome. We investigated the influence of protein intake on selected tryptophan and phenolic compounds, derived from both endogenous and colonic microbial metabolism. Furthermore, potential inter-species metabolic differences were studied. For this purpose, 29 healthy subjects were allocated to a high (n = 14) or low protein diet (n = 15) for 2 weeks. In addition, 20 wild-type FVB mice were randomized to a high protein or control diet for 21 days. Plasma and urine samples were analyzed with liquid chromatography-mass spectrometry for measurement of tryptophan and phenolic metabolites. In human subjects, we observed significant changes in plasma level and urinary excretion of indoxyl sulfate (P 0.004 and P 0.001), and in urinary excretion of indoxyl glucuronide (P 0.01), kynurenic acid (P 0.006) and quinolinic acid (P 0.02). In mice, significant differences were noted in plasma tryptophan (P 0.03), indole-3-acetic acid (P 0.02), p-cresyl glucuronide (P 0.03), phenyl sulfate (P 0.004) and phenylacetic acid (P 0.01). Thus, dietary protein intake affects plasma levels and generation of various mammalian metabolites, suggesting an influence on both endogenous and colonic microbial metabolism. Metabolite changes are dissimilar between human subjects and mice, pointing to inter-species metabolic differences with respect to protein intake.

PMID:26469515 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4607412 Poesen R et al; PLoS One 10 (10): e0140820 (2015)


Burkholderia heleia PAK1-2 is a potent biocontrol agent isolated from rice rhizosphere, as it prevents bacterial rice seedling blight disease caused by Burkholderia plantarii. Here, we isolated a non-antibacterial metabolite from the culture fluid of B. heleia PAK1-2 that was able to suppress B. plantarii virulence and subsequently identified as indole-3-acetic acid (IAA). IAA suppressed the production of tropolone in B. plantarii in a dose-dependent manner without any antibacterial and quorum quenching activity, suggesting that IAA inhibited steps of tropolone biosynthesis. Consistent with this, supplementing cultures of B. plantarii with either L-[ring-(2)H5]phenylalanine or [ring-(2)H2~5]phenylacetic acid revealed that phenylacetic acid (PAA), which is the dominant metabolite during the early growth stage, is a direct precursor of tropolone. Exposure of B. plantarii to IAA suppressed production of both PAA and tropolone. These data particularly showed that IAA produced by B. heleia PAK1-2 disrupts tropolone production during bioconversion of PAA to tropolone via the ring-rearrangement on the phenyl group of the precursor to attenuate the virulence of B. plantarii. B. heleia PAK1-2 is thus likely a microbial community coordinating bacterium in rhizosphere ecosystems, which never eliminates phytopathogens but only represses production of phytotoxins or bacteriocidal substances.

PMID:26935539 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4776283 Wang M et al; Sci Rep 6: 22596 doi: 10.1038/srep22596 (2016)


2-phenylethylamine is an endogenous constituent of the human brain and is implicated in cerebral transmission. This bioactive amine is also present in certain foodstuffs such as chocolate, cheese and wine and may cause undesirable side effects in susceptible individuals. Metabolism of 2-phenylethylamine to phenylacetaldehyde is catalyzed by monoamine oxidase B but the oxidation to its acid is usually ascribed to aldehyde dehydrogenase and the contribution of aldehyde oxidase and xanthine oxidase, if any, is ignored. The objective of this study was to elucidate the role of the molybdenum hydroxylases, aldehyde oxidase and xanthine oxidase, in the metabolism of phenylacetaldehyde derived from its parent biogenic amine. Treatments of 2-phenylethylamine with monoamine oxidase were carried out for the production of phenylacetaldehyde, as well as treatments of synthetic or enzymatic-generated phenylacetaldehyde with aldehyde oxidase, xanthine oxidase and aldehyde dehydrogenase. The results indicated that phenylacetaldehyde is metabolized mainly to phenylacetic acid with lower concentrations of 2-phenylethanol by all three oxidizing enzymes. Aldehyde dehydrogenase was the predominant enzyme involved in phenylacetaldehyde oxidation and thus it has a major role in 2-phenylethylamine metabolism with aldehyde oxidase playing a less prominent role. Xanthine oxidase does not contribute to the oxidation of phenylacetaldehyde due to low amounts being present in guinea pig. Thus aldehyde dehydrogenase is not the only enzyme oxidizing xenobiotic and endobiotic aldehydes and the role of aldehyde oxidase in such reactions should not be ignored.

Panoutsopoulos GI et al; Basic Clin Pharmacol Toxicol 95 (6): 273-9 (2004)


Phenylacetic acid, the major metabolite of phenylethylamine, has been identified and quantitated in rat brain regions by capillary column high-resolution gas chromatography mass spectrometry. Its distribution is heterogeneous and correlates with that of phenylethylamine. The values obtained were (ng/g +/- SEM): whole brain, 31.2 +/- 2.7; caudate nucleus, 64.6 +/- 6.5; hypothalamus, 60.1 +/- 7.4; cerebellum, 31.3 +/- 2.9; brainstem, 33.1 +/- 3.3, and the "rest," 27.6 +/- 3.0.

PMID:7077324 Durden DA, Boulton AA; J Neurochem 38 (6): 1532-6 (1982)


For more Metabolism/Metabolites (Complete) data for Phenylacetic acid (9 total), please visit the HSDB record page.


2-Phenylacetic acid is a known human metabolite of 3-hydroxyphenylacetic acid and 4-hydroxyphenylacetic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


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HK","customerAddress":"NO.4-1-10\/1, TILAK ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2025","qtr":"Q1","strtotime":1743100200,"product":"3-ETHOXY-4(ETHOXYCARBONYL)-PHENYLACETIC ACID CAS NO.: 99469-99-5 BATCH: 202405143-ETHOXY-4(ETHOXYCARBONYL)-PHENYLACETIC ACID CAS NO.: 99469-","address":"B.S.D.MARG, GOVANDI STATION ROAD,","city":"MUMBAI, MAHARASHTRA.","supplier":"GUANGZHOU GREENSYN PHARMA ","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"USV PRIVATE LIMITED","customerCountry":"INDIA","quantity":"100.00","actualQuantity":"100","unit":"KGS","unitRateFc":"275","totalValueFC":"27716.7","currency":"USD","unitRateINR":"24007.5","date":"28-Mar-2025","totalValueINR":"2400750","totalValueInUsd":"27716.7","indian_port":"Bombay Air","hs_no":"29339990","bill_no":"9163155","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"TECHNOLOGY INNOVATION BASE ROOM 614-616, DISTRICT D, VAT NO.80 LAN YUE RD CHINA","customerAddress":"B.S.D.MARG, GOVANDI STATION ROAD,"}]
18-Jan-2021
28-Mar-2025
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Looking for 103-82-2 / Phenylacetic Acid API manufacturers, exporters & distributors?

Phenylacetic Acid manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Phenylacetic Acid API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Phenylacetic Acid manufacturer or Phenylacetic Acid supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Phenylacetic Acid manufacturer or Phenylacetic Acid supplier.

PharmaCompass also assists you with knowing the Phenylacetic Acid API Price utilized in the formulation of products. Phenylacetic Acid API Price is not always fixed or binding as the Phenylacetic Acid Price is obtained through a variety of data sources. The Phenylacetic Acid Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Phenylacetic Acid

Synonyms

2-phenylacetic acid, Benzeneacetic acid, 103-82-2, Phenylethanoic acid, Alpha-toluic acid, Acetic acid, phenyl-

Cas Number

103-82-2

Unique Ingredient Identifier (UNII)

ER5I1W795A

About Phenylacetic Acid

Phenylacetic acid is a metabolite found in or produced by Saccharomyces cerevisiae.

Phenylacetic Acid Manufacturers

A Phenylacetic Acid manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Phenylacetic Acid, including repackagers and relabelers. The FDA regulates Phenylacetic Acid manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Phenylacetic Acid API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Phenylacetic Acid Suppliers

A Phenylacetic Acid supplier is an individual or a company that provides Phenylacetic Acid active pharmaceutical ingredient (API) or Phenylacetic Acid finished formulations upon request. The Phenylacetic Acid suppliers may include Phenylacetic Acid API manufacturers, exporters, distributors and traders.

click here to find a list of Phenylacetic Acid suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Phenylacetic Acid USDMF

A Phenylacetic Acid DMF (Drug Master File) is a document detailing the whole manufacturing process of Phenylacetic Acid active pharmaceutical ingredient (API) in detail. Different forms of Phenylacetic Acid DMFs exist exist since differing nations have different regulations, such as Phenylacetic Acid USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Phenylacetic Acid DMF submitted to regulatory agencies in the US is known as a USDMF. Phenylacetic Acid USDMF includes data on Phenylacetic Acid's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Phenylacetic Acid USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Phenylacetic Acid suppliers with USDMF on PharmaCompass.

Phenylacetic Acid GMP

Phenylacetic Acid Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Phenylacetic Acid GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Phenylacetic Acid GMP manufacturer or Phenylacetic Acid GMP API supplier for your needs.

Phenylacetic Acid CoA

A Phenylacetic Acid CoA (Certificate of Analysis) is a formal document that attests to Phenylacetic Acid's compliance with Phenylacetic Acid specifications and serves as a tool for batch-level quality control.

Phenylacetic Acid CoA mostly includes findings from lab analyses of a specific batch. For each Phenylacetic Acid CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Phenylacetic Acid may be tested according to a variety of international standards, such as European Pharmacopoeia (Phenylacetic Acid EP), Phenylacetic Acid JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Phenylacetic Acid USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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