Record Information
Creation Date2012-07-30 14:54:45 -0600
Update Date2015-09-13 12:56:14 -0600
Secondary Accession Numbers
  • ECMDB21171
Name:3-Hydroxycinnamic acid
Description3-hydroxycinnamic acid, also known as m-coumaric acid, is an aromatic acid. Research has shown that E. coli K-12 can grow with 3-hydroxycinnamic acid as the sole carbon source. (EcoCyc, PMID 6345502)
  • (2E)-3-(3-hydroxyphenyl)prop-2-enoate
  • (2E)-3-(3-hydroxyphenyl)-2-propenoate
  • (2E)-3-(3-hydroxyphenyl)-2-propenoic acid
  • (2E)-3-(3-hydroxyphenyl)acrylate
  • (2E)-3-(3-hydroxyphenyl)acrylic acid
  • (2E)-3-(3-hydroxyphenyl)prop-2-enoate
  • (2E)-3-(3-hydroxyphenyl)prop-2-enoic acid
  • (E)-3-(3-hydroxyphenyl)-2-propenoate
  • (E)-3-(3-hydroxyphenyl)-2-propenoic acid
  • 3'-Hydroxycinnamate
  • 3'-Hydroxycinnamic acid
  • 3-(3-Hydroxyphenyl)-2-Propenoate
  • 3-(3-Hydroxyphenyl)-2-Propenoic acid
  • 3-(3-Hydroxyphenyl)acrylate
  • 3-(3-Hydroxyphenyl)acrylic acid
  • 3-(3-Hydroxyphenyl)acrylsaeure
  • 3-(3-Hydroxyphenyl)prop-2-enoate
  • 3-(3-Hydroxyphenyl)prop-2-enoic acid
  • 3-Coumarate
  • 3-Coumaric acid
  • 3-Hydroxycinnamate
  • 3-Hydroxycinnamic acid
  • M-Coumarate
  • M-Coumaric acid
  • M-Hydroxy-Cinnamate
  • M-Hydroxy-Cinnamic acid
  • M-Hydroxycinnamate
  • M-Hydroxycinnamic acid
  • Trans-3-Coumarate
  • Trans-3-Coumaric acid
  • Trans-3-Hydroxycinnamate
  • Trans-3-Hydroxycinnamic acid
Chemical Formula:C9H8O3
Weight:Average: 164.158
Monoisotopic: 164.047344122
CAS number:588-30-7
IUPAC Name:(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid
Traditional IUPAC Name:m-coumaric acid
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
  • Cinnamic acid
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
Melting point:192-194 °C
Experimental Properties:
Predicted Properties
Water Solubility1.04 g/LALOGPS
pKa (Strongest Acidic)4.01ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m³·mol⁻¹ChemAxon
Polarizability16.37 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
SMPDB Pathways:
2-Oxopent-4-enoate metabolismPW001890 ThumbThumb?image type=greyscaleThumb?image type=simple
2-Oxopent-4-enoate metabolism 2PW002035 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Microbial metabolism in diverse environments ec01120
  • Phenylalanine metabolism ec00360
EcoCyc Pathways:
  • cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoate PWY-6690
Not Available
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udl-1691000000-331053d0d0b85549ac0bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udl-1691000000-331053d0d0b85549ac0bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1891000000-049e1d80dd47b23e8c28View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-2900000000-91ffd4c10eaed6a17632View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00y3-6390000000-f1a30e2fb9cd1fb11341View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03xr-0900000000-4259219e89806dfe2602View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-014i-4900000000-2157a17ec65ead35585eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00kf-9300000000-3325dd31a734dd4659bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-be33d196fbb525019f07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-d256885fb0f35d3d6680View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-be33d196fbb525019f07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0900000000-d256885fb0f35d3d6680View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-87be0242c9f5b426f6b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-9e4128fa078e73e71cbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-0900000000-d256885fb0f35d3d6680View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9100000000-1865c168df491277a4d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9000000000-296d14129321002679a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9700000000-6d29cdde66b32806de5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-9da76da83e0462c48acfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-bf33c5b8f5901c60b332View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-2900000000-11ae76e2fe36da1dfbe6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-b6bf0b46b2fa8324cf71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00kb-0900000000-1065251e7cf92f343533View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004i-9000000000-0a87c81608b3fbcee7c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-b5ad37fb931b464df7d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1900000000-c66c146ee9509bf8a413View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-9700000000-fcc332df0fcb818fe0e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-408ac0dd815354188750View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-146bae2da386ca2d4f1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-235b38f342376d1c9f90View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03xr-7900000000-61ee2ad0ad164a1f7550View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
Pubchem Compound ID637541
Kegg IDC12621
ChemSpider ID553147
Wikipedia IDM-coumaric_acid
BioCyc IDCPD-10797
EcoCyc IDCPD-10797


General function:
Involved in 3-(3-hydroxyphenyl)propionate hydroxylase activity
Specific function:
Catalyzes the insertion of one atom of molecular oxygen into position 2 of the phenyl ring of 3-(3- hydroxyphenyl)propionate (3-HPP) and hydroxycinnamic acid (3HCI)
Gene Name:
Uniprot ID:
Molecular weight:
3-(3-hydroxyphenyl)propanoate + NADH + O(2) = 3-(2,3-dihydroxyphenyl)propanoate + H(2)O + NAD(+).
(2E)-3-(3-hydroxyphenyl)prop-2-enoate + NADH + O(2) = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + H(2)O + NAD(+).


General function:
Involved in transmembrane transport
Specific function:
Could be a transporter for 3-phenylpropionate (hydrocinnamic acid)
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
Uniprot ID:
Molecular weight: