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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:50:48 UTC
Update Date2021-09-07 17:05:32 UTC
HMDB IDHMDB0032616
Secondary Accession Numbers
  • HMDB32616
Metabolite Identification
Common NameSinapic acid
DescriptionSinapic acid, also known as sinapinate, 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. Sinapic acid has been detected, but not quantified, in several different foods, such as strawberry guava, purple lavers, common verbena, ryes, and lupines. This could make sinapic acid a potential biomarker for the consumption of these foods. A sinapic acid in which the double bond has trans-configuration.
Structure
Data?1588108290
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
trans-SinapateHMDB
(e)-Sinapic acidHMDB
Synapitic acidHMDB
trans-Sinapinic acidHMDB
(e)-3,5-Dimethoxy-4-hydroxycinnamic acidHMDB
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acidHMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acidHMDB
e-Sinapinic acidHMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acidHMDB
trans-Sinapic acidHMDB
Sinapic acidChEBI
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 Molecular Properties
PropertyValueReference
Melting Point192 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Sinapic acid,1TMS,#12214.299https://arxiv.org/abs/1905.12712
Sinapic acid,1TMS,#22169.7712https://arxiv.org/abs/1905.12712
Sinapic acid,2TMS,#12201.4788https://arxiv.org/abs/1905.12712
Sinapic acid,1TBDMS,#12477.673https://arxiv.org/abs/1905.12712
Sinapic acid,1TBDMS,#22451.1287https://arxiv.org/abs/1905.12712
Sinapic acid,2TBDMS,#12735.2854https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00kr-3759000000-26099df97cd2adef2dc32014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-4390000000-ce04c31c3e4023faa7ee2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kr-2759000000-404687968a18ced29cd92017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kr-1869000000-618d42ab9681ecb062282017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9535000000-dc1aa60962d61ce2d9bb2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9636000000-15691f6a00fd74dadf7a2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kr-3759000000-26099df97cd2adef2dc32017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-1966000000-84b6d21b3c65f74d1b2d2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05di-1950000000-308e223e0595ec83666c2017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0umi-8196000000-afceb35e7a5f28ec225c2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-5590000000-92339c0e84f7bfd7f8552015-03-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-002e-0900000000-c7f7d78d04b4c61a02e12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0007-0900000000-76cfe991af651e6cec192017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0290000000-475d3684fdd4228e9c5d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-08fr-0940000000-780771eea370a78b609a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-1900000000-3e127fbdcf11519a02f32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-3900000000-d41ed2853570e017a98c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-006x-9600000000-668bfef76d2c295142162017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-1950000000-845dcc12144449b6b8c52017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-074m-1940000000-4eaf9a539449ae53a9702017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-1590000000-f69ac29a002b25accd732017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ar4-3940000000-64d09640303051f3b7742017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-9500000000-8fb01ded8d8100c7badf2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-9100000000-6b4758d6474e1684747b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00dl-2900000000-512d339f4cd5c1a36d792021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-2900000000-f1f1c513515bb228b4102021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-08mm-0930000000-725b42822634411b06e12021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0190000000-6e81a94093485194a43f2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1960000000-18717b9e874f0901ea682016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vj-2900000000-254ee08e710708eb65452016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-89ae701e731ef1f24fd72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0890000000-74c0bdbe7769b328017a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1910000000-69bbc48ce24397a342a22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0290000000-9de305bfb1242c5c3e102021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0980000000-368fb5936979c9a6e99d2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-3900000000-395e080ff0323f7c60bc2021-09-07View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)2015-03-12View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 464 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 464 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 464 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB031174
KNApSAcK IDC00002776
Chemspider ID553361
KEGG Compound IDC00482
BioCyc IDSINAPATE
BiGG IDNot Available
Wikipedia LinkSinapinic_acid
METLIN IDNot Available
PubChem Compound637775
PDB IDNot Available
ChEBI ID15714
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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.. .