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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2021-09-07 16:45:33 UTC
HMDB IDHMDB0002359
Secondary Accession Numbers
  • HMDB02359
Metabolite Identification
Common NamePhenylpropiolic acid
DescriptionPhenylpropiolic acid is an acetylenic compound that is propynoic acid in which the acetylenic hydrogen is replaced by a phenyl group. It is an alpha,beta-unsaturated monocarboxylic acid, an acetylenic compound and a member of benzenes. It derives from a propynoic acid. Phenylpropiolic acid is one of a number of phenylpropanoid, natural products occurring in plants pathways involved in plant resistance providing building units of physical barriers against pathogen invasion, synthesizing an array of antibiotic compounds, and producing signals implicated in the mounting of plant resistance. (PMID 15199968 ). Phenylpropiolic acid is a cis-pyrrolidinone that has been tested as an inhibitors of type II 17beta-hydroxysteroid dehydrogenase for the treatment of osteoporosis. (PMID 16806919 ). Phenylpropiolic acid (C6H5CCCO2H) is formed by the action of alcoholic potash on cinnamic acid dibromide (C6H5CHBrCHBrCO2H), crystallizes in long needles or prisms which melt at 136–137 °C. When heated with water to 120 °C, it yields phenylacetylene (C6H5CCH). Chromic acid oxidizes it to benzoic acid; zinc and acetic acid reduce it to cinnamic acid, C6H5CH=CHCO2H, whilst sodium amalgam reduces it to hydrocinnamic acid, C6H5CH2CH2CO2H. Ortho-nitrophenylpropiolic acid, NO2C6H4CCCO2H, prepared by the action of alcoholic potash on ortho-nitrocinnamic acid dibromide, crystallizes in needles which decompose when heated to 155–156 °C. It is readily converted into indigo.
Structure
Data?1582752245
Synonyms
ValueSource
3-Phenylpropiolic acidChEBI
3-Phenylpropynoic acidChEBI
beta-Phenylpropargylic acidChEBI
Phenylacetylene monocarboxylic acidChEBI
Phenylacetylenecarboxylic acidChEBI
Phenylpropynoic acidChEBI
3-PhenylpropiolateGenerator
3-PhenylpropynoateGenerator
b-PhenylpropargylateGenerator
b-Phenylpropargylic acidGenerator
beta-PhenylpropargylateGenerator
Β-phenylpropargylateGenerator
Β-phenylpropargylic acidGenerator
Phenylacetylene monocarboxylateGenerator
PhenylacetylenecarboxylateGenerator
PhenylpropynoateGenerator
PhenylpropiolateGenerator
3-Phenyl-2-propynoateHMDB
3-Phenyl-2-propynoic acidHMDB
3-Phenyl-propiolateHMDB
3-Phenyl-propiolic acidHMDB
Phenyl-(8ci)propiolateHMDB
Phenyl-(8ci)propiolic acidHMDB
Phenyl-propiolateHMDB
Phenyl-propiolic acidHMDB
PhenylpropioplateHMDB
Phenylpropioplic acidHMDB
Chemical FormulaC9H6O2
Average Molecular Weight146.1427
Monoisotopic Molecular Weight146.036779436
IUPAC Name3-phenylprop-2-ynoic acid
Traditional Namephenylpropiolic acid
CAS Registry Number637-44-5
SMILES
OC(=O)C#CC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)
InChI KeyXNERWVPQCYSMLC-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 DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point136 - 139 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP10(1.7) g/LALOGPS
logP10(2.15) g/LChemAxon
logS10(-2.9) g/LALOGPS
pKa (Strongest Acidic)2.77ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.45 m³·mol⁻¹ChemAxon
Polarizability14.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.30731661259
DarkChem[M-H]-129.13231661259
DeepCCS[M+H]+128.17830932474
DeepCCS[M-H]-125.27730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phenylpropiolic acidOC(=O)C#CC1=CC=CC=C12361.4Standard polar33892256
Phenylpropiolic acidOC(=O)C#CC1=CC=CC=C11287.1Standard non polar33892256
Phenylpropiolic acidOC(=O)C#CC1=CC=CC=C11415.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenylpropiolic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C#CC1=CC=CC=C11578.6Semi standard non polar33892256
Phenylpropiolic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C#CC1=CC=CC=C11793.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenylpropiolic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1900000000-f3dcdea0585a8167ee362017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylpropiolic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-9830000000-feb73790a25f137386f92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylpropiolic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropiolic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00mk-3900000000-03289f4e3836577721292012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropiolic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004i-9800000000-ebfac1366623441b4fab2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropiolic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-9100000000-b111b793437863f24a8c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropiolic acid 40V, Positive-QTOFsplash10-0fb9-9100000000-480dfc61257dac3007242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropiolic acid 10V, Positive-QTOFsplash10-00os-3900000000-c7f3388a9ad322e37bba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropiolic acid 20V, Positive-QTOFsplash10-004i-9800000000-03950939b02a4a226b5d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 10V, Positive-QTOFsplash10-004i-0900000000-9ccdda8aa55c7fd5f1792017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 20V, Positive-QTOFsplash10-0fb9-0900000000-39ffafabcb71dd5e4fb92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 40V, Positive-QTOFsplash10-0udi-2900000000-a61c9be6ba2e3e672a4b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 10V, Negative-QTOFsplash10-0002-0900000000-53fd8625b272fb8c08742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 20V, Negative-QTOFsplash10-0002-0900000000-c01f026883e9d8371e782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 40V, Negative-QTOFsplash10-0udi-0900000000-d89d4873b06625bc98b22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 10V, Positive-QTOFsplash10-004i-0900000000-6044d949db2e286e54402021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 20V, Positive-QTOFsplash10-0udi-0900000000-1f23da2395d60c7675822021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 40V, Positive-QTOFsplash10-0ufr-6900000000-eef250719433f4e474162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 10V, Negative-QTOFsplash10-0udj-0900000000-e164e953b1394208fd0d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 20V, Negative-QTOFsplash10-0udi-0900000000-b63c162ca0b38a8b1bb02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropiolic acid 40V, Negative-QTOFsplash10-0udi-4900000000-87bc643c2fbf1a8525c52021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022977
KNApSAcK IDNot Available
Chemspider ID62682
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenylpropiolic_acid
METLIN ID6644
PubChem Compound69475
PDB IDNot Available
ChEBI ID90355
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. La Camera S, Gouzerh G, Dhondt S, Hoffmann L, Fritig B, Legrand M, Heitz T: Metabolic reprogramming in plant innate immunity: the contributions of phenylpropanoid and oxylipin pathways. Immunol Rev. 2004 Apr;198:267-84. [PubMed:15199968 ]
  2. Wood J, Bagi CM, Akuche C, Bacchiocchi A, Baryza J, Blue ML, Brennan C, Campbell AM, Choi S, Cook JH, Conrad P, Dixon BR, Ehrlich PP, Gane T, Gunn D, Joe T, Johnson JS, Jordan J, Kramss R, Liu P, Levy J, Lowe DB, McAlexander I, Natero R, Redman AM, Scott WJ, Town C, Wang M, Wang Y, Zhang Z: 4,5-Disubstituted cis-pyrrolidinones as inhibitors of type II 17beta-hydroxysteroid dehydrogenase. Part 3. Identification of lead candidate. Bioorg Med Chem Lett. 2006 Sep 15;16(18):4965-8. Epub 2006 Jun 27. [PubMed:16806919 ]