Sinapic acid (CHEM021938)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:16:10 UTC
Update Date2016-11-09 01:17:23 UTC
Accession NumberCHEM021938
Identification
Common NameSinapic acid
ClassSmall Molecule
DescriptionA sinapic acid in which the double bond has trans-configuration.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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, HMDB
(e)-Sinapic acidMeSH, HMDB
Synapitic acidMeSH, HMDB
trans-Sinapinic acidMeSH, HMDB
(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 Mass224.210 g/mol
Monoisotopic Mass224.068 g/mol
CAS Registry Number530-59-6
IUPAC Name(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
Traditional Namesinapinic acid
SMILESCOC1=CC(\C=C\C(O)=O)=CC(OC)=C1O
InChI IdentifierInChI=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 )
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00kr-3759000000-26099df97cd2adef2dc3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-4390000000-ce04c31c3e4023faa7eeSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kr-2759000000-404687968a18ced29cd9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kr-1869000000-618d42ab9681ecb06228Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9535000000-dc1aa60962d61ce2d9bbSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9636000000-15691f6a00fd74dadf7aSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kr-3759000000-26099df97cd2adef2dc3Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-1966000000-84b6d21b3c65f74d1b2dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05di-1950000000-308e223e0595ec83666cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0umi-8196000000-afceb35e7a5f28ec225cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-002e-0900000000-c7f7d78d04b4c61a02e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0007-0900000000-76cfe991af651e6cec19Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0290000000-475d3684fdd4228e9c5dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-08fr-0940000000-780771eea370a78b609aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-1900000000-3e127fbdcf11519a02f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-3900000000-d41ed2853570e017a98cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-006x-9600000000-668bfef76d2c29514216Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-1950000000-845dcc12144449b6b8c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-074m-1940000000-4eaf9a539449ae53a970Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-1590000000-f69ac29a002b25accd73Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ar4-3940000000-64d09640303051f3b774Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-9500000000-8fb01ded8d8100c7badfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-9100000000-6b4758d6474e1684747bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00dl-2900000000-512d339f4cd5c1a36d79Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-2900000000-f1f1c513515bb228b410Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-08mm-0930000000-725b42822634411b06e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00kf-9400000000-e70224cdae252d3c8e18Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-45fe03024d3082fc695eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0btc-0940000000-61107acc0e4d467950bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0190000000-6e81a94093485194a43fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1960000000-18717b9e874f0901ea68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vj-2900000000-254ee08e710708eb6545Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-89ae701e731ef1f24fd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0890000000-74c0bdbe7769b328017aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1910000000-69bbc48ce24397a342a2Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-5590000000-92339c0e84f7bfd7f855Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB08587
HMDB IDHMDB0032616
FooDB IDFDB010557
Phenol Explorer ID464
KNApSAcK IDC00002776
BiGG IDNot Available
BioCyc IDSINAPATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSinapinic_acid
Chemspider ID553361
ChEBI ID15714
PubChem Compound ID637775
Kegg Compound IDC00482
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.