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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:56 UTC
HMDB IDHMDB0000543
Secondary Accession Numbers
  • HMDB00543
Metabolite Identification
Common NameBenzenebutanoic acid
DescriptionBenzenebutanoic acid (also known as 4-phenylbutyrate, or 4-PBA) is the oral form of butyrate, which is known to be a transcriptional regulator. Sodium-4-PBA has been shown to induce fetal hemoglobin, and it has been used in clinical trials for sickle cell anemia and β-thalassemia. Because gene expression profiles became more differentiated, it is in phase I trials in several different malignant disorders. The potential for therapeutic benefit in cystic fibrosis (CF) resides in an additional mechanism, involving protein folding and the ER (endoplasmic reticulum) environment (PMID 12458151 ). 4-PBA is a drug that was developed to treat elevated blood ammonia in urea cycle disorders, a histone deacetylase inhibitor that promotes mutation ΔF508 cystic fibrosis transmembrane conductance regulator (CFTR) trafficking (PMID 16798551 ).
Structure
Thumb
Synonyms
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name4-phenylbutanoic acid
Traditional Name4-phenylbutyric acid
CAS Registry Number1821-12-1
SMILES
OC(=O)CCCC1=CC=CC=C1
InChI Identifier
InChI=1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12)
InChI KeyOBKXEAXTFZPCHS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point47 - 49 °CNot Available
Boiling Point290.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility18 mg/mLNot Available
LogP2.42HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Pancreas
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06819
Phenol Explorer Compound IDNot Available
FooDB IDFDB022106
KNApSAcK IDNot Available
Chemspider ID4611
KEGG Compound IDNot Available
BioCyc IDCPD-14367
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5528
PubChem Compound4775
PDB IDNot Available
ChEBI ID41500
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1206621
References
Synthesis ReferenceGalat, Alexander. The reaction of phenylpyruvic acid and related compounds with ammonia. Journal of the American Chemical Society (1950), 72 4436-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Koyama M, Watanabe N, Asakawa N: Radioimmunoassay for ubenimex in human serum. J Pharm Biomed Anal. 1992 Feb-Mar;10(2-3):137-40. [PubMed:1391092 ]
  2. Singh L, Field MJ, Hill DR, Horwell DC, McKnight AT, Roberts E, Tang KW, Woodruff GN: Peptoid CCK receptor antagonists: pharmacological evaluation of CCKA, CCKB and mixed CCKA/B receptor antagonists. Eur J Pharmacol. 1995 Nov 14;286(2):185-91. [PubMed:8605955 ]
  3. Powell K, Zeitlin PL: Therapeutic approaches to repair defects in deltaF508 CFTR folding and cellular targeting. Adv Drug Deliv Rev. 2002 Dec 5;54(11):1395-408. [PubMed:12458151 ]
  4. Kerem E: Mutation specific therapy in CF. Paediatr Respir Rev. 2006;7 Suppl 1:S166-9. Epub 2006 Jun 5. [PubMed:16798551 ]