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Sinapaldehyde (FDB001515)

Record Information
Version1.0
Creation date2010-04-08 22:05:00 UTC
Update date2019-11-26 02:56:33 UTC
Primary IDFDB001515
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSinapaldehyde
DescriptionSinapaldehyde, also known as (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-propenal or (E)-sinapoyl aldehyde, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Sinapaldehyde is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Sinapaldehyde can be synthesized from cinnamaldehyde. Sinapaldehyde can also be synthesized into 4-acetoxy-3,5-dimethoxy-trans-cinnamaldehyde. Sinapaldehyde can be found in a number of food items such as angelica, saskatoon berry, rubus (blackberry, raspberry), and lemon verbena, which makes sinapaldehyde a potential biomarker for the consumption of these food products. In Arabidopsis thaliana, this compound is part of the lignin biosynthesis pathway. The enzyme dihydroflavonol 4-reductase uses sinapaldehyde and NADPH to produce sinapyl alcohol and NADP+ .
CAS Number4206-58-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.68 g/LALOGPS
logP2.22ALOGPS
logP1.36ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)8.94ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.04 m³·mol⁻¹ChemAxon
Polarizability21.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H12O4
IUPAC name(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
InChI IdentifierInChI=1S/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3/b4-3+
InChI KeyCDICDSOGTRCHMG-ONEGZZNKSA-N
Isomeric SMILESCOC1=CC(\C=C\C=O)=CC(OC)=C1O
Average Molecular Weight208.2106
Monoisotopic Molecular Weight208.073558872
Classification
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Cinnamaldehyde
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Methoxybenzene
  • Anisole
  • Phenoxy compound
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated aldehyde
  • Enal
  • Ether
  • Aldehyde
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
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
GC-MSSinapaldehyde, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-006t-2960000000-b4576a258cd5a5cea23dSpectrum
GC-MSSinapaldehyde, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-006t-1961000000-deeb715597e211683e4bSpectrum
Predicted GC-MSSinapaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05r0-1920000000-13ed408a328d582b73feSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0490000000-23b588b89be53c4edcdf2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-2950000000-193c1b8d29eea545ebba2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07fu-3900000000-f390ac8bb92b8e87d3512016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-c3c4a3dbbc311470ad202016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1890000000-2a1ae4fc54b7f61f45f92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rf-3900000000-2504a877b635741aa0132016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC05610
Pubchem Compound ID5280802
Pubchem Substance IDNot Available
ChEBI ID27949
Phenol-Explorer ID631
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDSINAPALDEHYDE
BIGG IDNot Available
KNApSAcK IDC00002775
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti edemicDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— 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.