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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:50:48 UTC
Update Date2019-07-23 06:11:23 UTC
HMDB IDHMDB0032616
Secondary Accession Numbers
  • HMDB32616
Metabolite Identification
Common NameSinapic acid
DescriptionSinapic acid (CAS: 530-59-6) is found in American cranberry. Sinapic acid is a common constituent of plants and fruit.
Structure
Data?1563862283
Synonyms
ValueSource
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acidChEBI
SINAPINATEChEBI
Sinapinic acidChEBI
3,5-Dimethoxy-4-hydroxycinnamic acidKegg
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoateGenerator
3,5-Dimethoxy-4-hydroxycinnamateGenerator
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-(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
Sinapic acidChEBI
trans-SinapateGenerator
(e)-Sinapic acidMeSH
Synapitic acidMeSH
trans-Sinapinic acidMeSH
(E)-3,5-Dimethoxy-4-hydroxycinnamic acidHMDB
(E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acidHMDB
(E)-Sinapic acidHMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acidHMDB
E-Sinapinic acidHMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acidHMDB
trans-Sinapic 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 Number7362-37-0
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
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
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

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-2.6ALOGPS
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00kr-3759000000-26099df97cd2adef2dc3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-4390000000-ce04c31c3e4023faa7eeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kr-2759000000-404687968a18ced29cd9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kr-1869000000-618d42ab9681ecb06228JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9535000000-dc1aa60962d61ce2d9bbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9636000000-15691f6a00fd74dadf7aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kr-3759000000-26099df97cd2adef2dc3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-1966000000-84b6d21b3c65f74d1b2dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05di-1950000000-308e223e0595ec83666cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0umi-8196000000-afceb35e7a5f28ec225cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-002e-0900000000-c7f7d78d04b4c61a02e1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0007-0900000000-76cfe991af651e6cec19JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0290000000-475d3684fdd4228e9c5dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-08fr-0940000000-780771eea370a78b609aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-1900000000-3e127fbdcf11519a02f3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-3900000000-d41ed2853570e017a98cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-006x-9600000000-668bfef76d2c29514216JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-1950000000-845dcc12144449b6b8c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-074m-1940000000-4eaf9a539449ae53a970JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-1590000000-f69ac29a002b25accd73JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ar4-3940000000-64d09640303051f3b774JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0190000000-6e81a94093485194a43fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1960000000-18717b9e874f0901ea68JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vj-2900000000-254ee08e710708eb6545JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-89ae701e731ef1f24fd7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0890000000-74c0bdbe7769b328017aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1910000000-69bbc48ce24397a342a2JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-5590000000-92339c0e84f7bfd7f855JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not Quantified Adult (>18 years old)Both
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB08587
Phenol Explorer Compound 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 IDNot Available
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.. .