Record Information
Version1.0
Creation date2010-04-08 22:11:07 UTC
Update date2018-05-29 01:10:04 UTC
Primary IDFDB014170
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-Hydroxyferulic acid
Description3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid, also known as trans-5-hydroxyferulic acid or 3-methoxy-4,5-dihydroxy-trans-cinnamic acid, 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. 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid has been detected, but not quantified in, several different foods, such as asian pears, lemon thymes, sweet cherries, annual wild rices, and ucuhuba. This could make 3-(3,4-dihydroxy-5-methoxy)-2-propenoic acid a potential biomarker for the consumption of these foods.
CAS Number1782-55-4
Structure
Thumb
Synonyms
SynonymSource
(2E)-3-(3,4-Dihydroxy-5-methoxyphenyl)-2-propenoic acidChEBI
3-Methoxy-4,5-dihydroxy-trans-cinnamic acidChEBI
trans-5-Hydroxyferulic acidChEBI
(2E)-3-(3,4-Dihydroxy-5-methoxyphenyl)-2-propenoateGenerator
3-Methoxy-4,5-dihydroxy-trans-cinnamateGenerator
trans-5-HydroxyferulateGenerator
3-(3,4-Dihydroxy-5-methoxy)-2-propenoateGenerator
3,4-Dihydroxy-5-methoxycinnamoic acidHMDB
3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid, 9ciHMDB
3-(3,4-Dihydroxy-5-methoxyphenyl)-2-propenoic acidHMDB
3-Methoxycaffeic acidHMDB
5-HydroxyferulateHMDB
5-Hydroxyferulic acidHMDB
HFLHMDB
5-Hydroxyferulate methyl esterGenerator
2-Propenoic acid, 3-(3,4-dihydroxy-5-methoxyphenyl)-biospider
3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility1.04 g/LALOGPS
logP1.41ALOGPS
logP1.37ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.48 m³·mol⁻¹ChemAxon
Polarizability20.31 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H10O5
IUPAC name(2E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C10H10O5/c1-15-8-5-6(2-3-9(12)13)4-7(11)10(8)14/h2-5,11,14H,1H3,(H,12,13)/b3-2+
InChI KeyYFXWTVLDSKSYLW-NSCUHMNNSA-N
Isomeric SMILESCOC1=CC(\C=C\C(O)=O)=CC(O)=C1O
Average Molecular Weight210.1834
Monoisotopic Molecular Weight210.05282343
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
  • Hydroxycinnamic acid
  • Coumaric acid or derivatives
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.14%; H 4.80%; O 38.06%DFC
Melting PointMp 182° (168-170° dec)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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-0910000000-edb7cb180844171b184bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-6039700000-818fd1c6815f0b1bf5f0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0970000000-6f1608973608646a6815JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-1910000000-99bedde5d4b95d2a72eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-3900000000-db5c30fefbe69f4bf23aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0290000000-25c9e8b31be5cda28840JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0950000000-6b6628733be09dd12decJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000g-2900000000-426d3db7318485c7e916JSpectraViewer
ChemSpider ID394087
ChEMBL IDNot Available
KEGG Compound IDC05619
Pubchem Compound ID446834
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35484
CRC / DFC (Dictionary of Food Compounds) IDBJK28-F:JOL14-W
EAFUS IDNot Available
Dr. Duke ID5-HYDROXY-TRANS-FERULIC-ACID
BIGG IDNot Available
KNApSAcK IDC00007336
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 / BioactivitiesNot Available
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).