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trans-Sinapic acid (FDB010557)

Record Information
Version1.0
Creation date2010-04-08 22:09:11 UTC
Update date2020-02-24 19:10:59 UTC
Primary IDFDB010557
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-Sinapic 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 is an odorless tasting compound. Sinapic acid is found, on average, in the highest concentration within a few different foods, such as sunflowers (Helianthus annuus), olives (Olea europaea), and garden onions (Allium cepa) and in a lower concentration in soy beans (Glycine max), potatos (Solanum tuberosum), and yellow wax beans (Phaseolus vulgaris). Sinapic acid has also been detected, but not quantified in, several different foods, such as wild rice (Zizania), java plums (Syzygium cumini), american pokeweeds (Phytolacca americana), irish mosses (Chondrus crispus), and groundcherries (Physalis). This could make sinapic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sinapic acid.
CAS Number530-59-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H12O5
IUPAC name(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
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
Isomeric SMILESCOC1=CC(\C=C\C(O)=O)=CC(OC)=C1O
Average Molecular Weight224.21
Monoisotopic Molecular Weight224.068473494
Classification
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
Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 58.93%; H 5.39%; O 35.68%DFC
    Melting PointMp 192°DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-00di-5590000000-92339c0e84f7bfd7f8552015-03-01View Spectrum
    GC-MStrans-Sinapic acid, 2 TMS, GC-MS Spectrumsplash10-00kr-3759000000-26099df97cd2adef2dc3Spectrum
    GC-MStrans-Sinapic acid, non-derivatized, GC-MS Spectrumsplash10-00di-4390000000-ce04c31c3e4023faa7eeSpectrum
    GC-MStrans-Sinapic acid, non-derivatized, GC-MS Spectrumsplash10-00kr-2759000000-404687968a18ced29cd9Spectrum
    GC-MStrans-Sinapic acid, non-derivatized, GC-MS Spectrumsplash10-00kr-1869000000-618d42ab9681ecb06228Spectrum
    GC-MStrans-Sinapic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9535000000-dc1aa60962d61ce2d9bbSpectrum
    GC-MStrans-Sinapic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9636000000-15691f6a00fd74dadf7aSpectrum
    GC-MStrans-Sinapic acid, non-derivatized, GC-MS Spectrumsplash10-00kr-3759000000-26099df97cd2adef2dc3Spectrum
    GC-MStrans-Sinapic acid, non-derivatized, GC-MS Spectrumsplash10-000i-1966000000-84b6d21b3c65f74d1b2dSpectrum
    Predicted GC-MStrans-Sinapic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05di-1950000000-308e223e0595ec83666cSpectrum
    Predicted GC-MStrans-Sinapic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0umi-8196000000-afceb35e7a5f28ec225cSpectrum
    Predicted GC-MStrans-Sinapic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-002e-0900000000-c7f7d78d04b4c61a02e12017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0007-0900000000-76cfe991af651e6cec192017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0290000000-475d3684fdd4228e9c5d2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-08fr-0940000000-780771eea370a78b609a2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-1900000000-3e127fbdcf11519a02f32017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-3900000000-d41ed2853570e017a98c2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-006x-9600000000-668bfef76d2c295142162017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-1950000000-845dcc12144449b6b8c52017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-074m-1940000000-4eaf9a539449ae53a9702017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-1590000000-f69ac29a002b25accd732017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ar4-3940000000-64d09640303051f3b7742017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-9500000000-8fb01ded8d8100c7badf2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-9100000000-6b4758d6474e1684747b2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00dl-2900000000-512d339f4cd5c1a36d792021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-2900000000-f1f1c513515bb228b4102021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-08mm-0930000000-725b42822634411b06e12021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00kf-9400000000-e70224cdae252d3c8e182021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-45fe03024d3082fc695e2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0btc-0940000000-61107acc0e4d467950bf2021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0190000000-6e81a94093485194a43f2016-08-02View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1960000000-18717b9e874f0901ea682016-08-02View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vj-2900000000-254ee08e710708eb65452016-08-02View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-89ae701e731ef1f24fd72016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0890000000-74c0bdbe7769b328017a2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1910000000-69bbc48ce24397a342a22016-08-03View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)Spectrum
    ChemSpider ID553361
    ChEMBL IDCHEMBL109341
    KEGG Compound IDC00482
    Pubchem Compound ID637775
    Pubchem Substance IDNot Available
    ChEBI ID15714
    Phenol-Explorer ID464
    DrugBank IDDB08587
    HMDB IDHMDB32616
    CRC / DFC (Dictionary of Food Compounds) IDBJK28-F:FDD01-L
    EAFUS IDNot Available
    Dr. Duke ID4-HYDROXY-3,5-DIMETHOXYCINNAMIC-ACID|SINAPIC-ACID|SINAPINIC-ACID|TRANS-SINAPIC-ACID
    BIGG IDNot Available
    KNApSAcK IDC00002776
    HET IDSXX
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDrw1184741
    SuperScent IDNot Available
    Wikipedia IDSinapinic_acid
    Phenol-Explorer Metabolite ID464
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    anti peroxynitriteDUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    fungicide24127 A substance used to destroy fungal pests.DUKE
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    odorless
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.