Record Information
Version1.0
Creation date2010-04-08 22:11:07 UTC
Update date2019-11-26 03:09:37 UTC
Primary IDFDB014170
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-Hydroxyferulic acid
Description5-Hydroxyferulic acid, also known as trans-5-hydroxyferulate, 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. 5-Hydroxyferulic acid has been detected, but not quantified in, several different foods, such as common chokecherries (Prunus virginiana), cupuaçus (Theobroma grandiflorum), persimmons (Diospyros), black huckleberries (Gaylussacia baccata), and climbing beans (Vigna umbellata). This could make 5-hydroxyferulic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Hydroxyferulic acid.
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
5-HydroxyferulateGenerator
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-Hydroxyferulic acidHMDB
HFLHMDB
5-Hydroxyferulate methyl esterGenerator
3-(3,4-Dihydroxy-5-methoxy)-2-propenoateGenerator
3,4-Dihydroxy-5-methoxycinnamic acidHMDB
E-5-Hydroxyferulic acidHMDB
3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acidHMDB
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5-Hydroxyferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-0910000000-edb7cb180844171b184bSpectrum
Predicted GC-MS5-Hydroxyferulic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-6039700000-818fd1c6815f0b1bf5f0Spectrum
Predicted GC-MS5-Hydroxyferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-Hydroxyferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0970000000-6f1608973608646a68152016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-1910000000-99bedde5d4b95d2a72ea2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-3900000000-db5c30fefbe69f4bf23a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0290000000-25c9e8b31be5cda288402016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0950000000-6b6628733be09dd12dec2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000g-2900000000-426d3db7318485c7e9162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-0690000000-3d076d9d2c8322ea32d82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ls-0900000000-075ce6e6c6eb242ff7c22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-3920000000-b91d58bedeef6007bb242021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0910000000-198b07c641d6eb666e072021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0296-0910000000-229335782ae991df22032021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9600000000-365cec17f27513fd80432021-09-24View Spectrum
NMRNot Available
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).