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Record Information
Version1.0
Created at2006-05-22 14:17:50 UTC
Updated at2021-06-29 00:47:33 UTC
NP-MRD IDNP0000270
Secondary Accession NumbersNone
Natural Product 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
Thumb
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 Mass146.1427 Da
Monoisotopic Mass146.03678 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Plantae
  • 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
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point136 - 139 °CNot Available
    Boiling PointNot AvailableNot Available
    Water SolubilityNot AvailableNot Available
    LogPNot AvailableNot Available
    Predicted Properties
    PropertyValueSource
    Water Solubility0.2 g/LALOGPS
    logP1.7ALOGPS
    logP2.15ChemAxon
    logS-2.9ALOGPS
    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
    HMDB IDHMDB0002359
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB 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
    Good Scents IDNot Available
    References
    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 ]
    3. Zielinski M, Zielinska A, Papiernik-Zielinska H, Ogrinc N, Kobal I: Carbon isotope fractionation in the decarboxylation of phenylpropiolic acid in hydrogen donating media. Isotopes Environ Health Stud. 2001;37(3):239-52. doi: 10.1080/10256010108033299. [PubMed:11924854 ]
    4. Okuma K, Koda M, Maekawa S, Shioji K, Inoue T, Kurisaki T, Wakita H, Yokomori Y: Reaction of thioketones with propiolic acids. Org Biomol Chem. 2006 Jul 21;4(14):2745-52. doi: 10.1039/b605068a. Epub 2006 Jun 12. [PubMed:16826299 ]
    5. Arderne C, Olivier DK, Ndinteh DT: Charge-assisted hydrogen bonding in salts of 2-amino-1H-benzimidazole with 3-phenylpropynoic acid and oct-2-ynoic acid. Acta Crystallogr C Struct Chem. 2015 Feb;71(Pt 2):146-51. doi: 10.1107/S2053229615001047. Epub 2015 Jan 24. [PubMed:25652283 ]