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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:50:48 UTC
Update Date2017-12-07 03:19:57 UTC
HMDB IDHMDB0032616
Secondary Accession Numbers
  • HMDB32616
Metabolite Identification
Common NameSinapic acid
DescriptionSinapic acid is found in american cranberry. Sinapic acid is a common constituent of plants and fruit
Structure
Thumb
Synonyms
ValueSource
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acidChEBI
SINAPINATEChEBI
Sinapinic acidChEBI
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoateGenerator
SinapateGenerator
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acidHMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acidHMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acidHMDB
3,5-Dimethoxy-4-hydroxycinnamic acidHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-(2E)-2-propenoic acidHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-(e)-2-propenoic acidHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acidHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acidHMDB
4-Hydroxy-3,5-dimethoxy-(e)-cinnamic acidHMDB
4-Hydroxy-3,5-dimethoxycinnamic acidHMDB
trans-3,5-Dimethoxy-4-hydroxycinnamic acidHMDB
Chemical FormulaC11H12O5
Average Molecular Weight224.21
Monoisotopic Molecular Weight224.068473494
IUPAC Name(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
Traditional Namesinapinic acid
CAS Registry Number530-59-6
SMILES
COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O
InChI Identifier
InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+
InChI KeyPCMORTLOPMLEFB-ONEGZZNKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxycinnamic acids. These are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassCinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
  • 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid (CHEBI:15714 )
  • Sinapate derivatives (C00482 )
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point192 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.63 g/LALOGPS
logP1.63ALOGPS
logP1.52ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.97 m³·mol⁻¹ChemAxon
Polarizability22.32 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00kr-3759000000-26099df97cd2adef2dc3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-4390000000-ce04c31c3e4023faa7eeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kr-2759000000-404687968a18ced29cd9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kr-1869000000-618d42ab9681ecb06228View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9535000000-dc1aa60962d61ce2d9bbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9636000000-15691f6a00fd74dadf7aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kr-3759000000-26099df97cd2adef2dc3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-1966000000-84b6d21b3c65f74d1b2dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05di-1950000000-308e223e0595ec83666cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0umi-8196000000-afceb35e7a5f28ec225cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-002e-0900000000-c7f7d78d04b4c61a02e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0007-0900000000-76cfe991af651e6cec19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0290000000-475d3684fdd4228e9c5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-08fr-0940000000-780771eea370a78b609aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-1900000000-3e127fbdcf11519a02f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-3900000000-d41ed2853570e017a98cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-006x-9600000000-668bfef76d2c29514216View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-1950000000-845dcc12144449b6b8c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-074m-1940000000-4eaf9a539449ae53a970View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-1590000000-f69ac29a002b25accd73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ar4-3940000000-64d09640303051f3b774View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0190000000-6e81a94093485194a43fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1960000000-18717b9e874f0901ea68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vj-2900000000-254ee08e710708eb6545View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-89ae701e731ef1f24fd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0890000000-74c0bdbe7769b328017aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1910000000-69bbc48ce24397a342a2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-5590000000-92339c0e84f7bfd7f855View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 464 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 464 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 464 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID464
Phenol Explorer Metabolite ID464
FoodDB IDFDB010557
KNApSAcK IDC00002776
Chemspider ID553361
KEGG Compound IDC00482
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSinapinic_acid
METLIN IDNot Available
PubChem Compound637775
PDB IDSXX
ChEBI ID15714
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yun KJ, Koh DJ, Kim SH, Park SJ, Ryu JH, Kim DG, Lee JY, Lee KT: Anti-inflammatory effects of sinapic acid through the suppression of inducible nitric oxide synthase, cyclooxygase-2, and proinflammatory cytokines expressions via nuclear factor-kappaB inactivation. J Agric Food Chem. 2008 Nov 12;56(21):10265-72. doi: 10.1021/jf802095g. Epub 2008 Oct 9. [PubMed:18841975 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .