Dihydroferulic acid (CHEM041677)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:38:35 UTC
Update Date2016-11-09 01:22:31 UTC
Accession NumberCHEM041677
Identification
Common NameDihydroferulic acid
ClassSmall Molecule
DescriptionA monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Dihydroconiferylic acidChEBI
3-(4-Hydroxy-3-methoxyphenyl)propionateGenerator
DihydroconiferylateGenerator
DihydroferulateGenerator
HydroferulateHMDB
(4-Hydroxy-3-methoxyphenyl)propionic acidHMDB
3-(3'-Methoxy-4'-hydroxyphenyl)propionic acidHMDB
3-(3-Methoxy-4-hydroxyphenyl)propanoic acidHMDB
3-(3-Methoxy-4-hydroxyphenyl)propionic acidHMDB
3-(3’-methoxy-4’-hydroxyphenyl)propionic acidHMDB
3-(4-Hydroxy-3-methoxyphenyl)propanoic acidHMDB
3-Methoxy-4-hydroxyphenylpropionic acidHMDB
3-Methoxyphloretic acidHMDB
4-Hydroxy-3-methoxybenzenepropanoic acidHMDB
DHFAHMDB
Shorbic acidHMDB
beta-(4-Hydroxy-3-methoxyphenyl)propionic acidHMDB
beta-3-Methoxy-4-hydroxyphenylpropionic acidHMDB
Β-(4-hydroxy-3-methoxyphenyl)propionic acidHMDB
Β-3-methoxy-4-hydroxyphenylpropionic acidHMDB
3-(4'-Hydroxy-3'-methoxyphenyl)propanoic acidHMDB
4-Hydroxy-3-methoxyhydrocinnamic acidPhytoBank
4-Hydroxy-3-methoxybenzenepropionic acidPhytoBank
(4-Hydroxy-3-methoxyphenyl)propanoic acidPhytoBank
3-(3'-Methoxy-4'-hydroxyphenyl)propanoic acidPhytoBank
3-(3’-Methoxy-4’-hydroxyphenyl)propanoic acidPhytoBank
3-Methoxy-4-hydroxyphenylpropanoic acidPhytoBank
alpha,beta-Dihydroferulic acidPhytoBank
α,β-Dihydroferulic acidPhytoBank
beta-(4-Hydroxy-3-methoxyphenyl)propanoic acidPhytoBank
β-(4-Hydroxy-3-methoxyphenyl)propanoic acidPhytoBank
beta-3-Methoxy-4-hydroxyphenylpropanoic acidPhytoBank
β-3-Methoxy-4-hydroxyphenylpropanoic acidPhytoBank
3-(4-Hydroxy-3-methoxyphenyl) propanoic acidHMDB
Chemical FormulaC10H12O4
Average Molecular Mass196.200 g/mol
Monoisotopic Mass196.074 g/mol
CAS Registry NumberNot Available
IUPAC Name3-(4-hydroxy-3-methoxyphenyl)propanoic acid
Traditional Namehomovanillinic acid
SMILESCOC1=C(O)C=CC(CCC(O)=O)=C1
InChI IdentifierInChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)
InChI KeyBOLQJTPHPSDZHR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.3 g/LALOGPS
logP1.03ALOGPS
logP1.59ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.95ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.41 m³·mol⁻¹ChemAxon
Polarizability19.8 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-0900000000-326c8295f745d6de85d0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-9053000000-50b6ef8efef449290129Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-0e26134b0d0191f7ee92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ug1-0900000000-7168875369e00ead2dcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbr-5900000000-7d74ece7efd4fcc57d7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-eb9b945ab0bf9d6f5dc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-aa8130dbec23e196888aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-7900000000-b403cda9802707e7ecbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0900000000-b4f6ef22cb5f85d71beaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-0f31db1df2ab8b8671c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kxr-9600000000-3d47fb450748aac59428Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-9500000000-1a3e759636e4322e4e58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-4900000000-f63426aee31341317b0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-2900000000-a9a9315636f849a6d02aSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0062121
FooDB IDFDB029987
Phenol Explorer IDNot Available
KNApSAcK IDC00040946
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID86612
PubChem Compound ID14340
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11368919
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11693915
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17469871
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19157126
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21676405
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23904092
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23982107
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24947504
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24949277
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25261518
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25644343
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=25809126
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=26471074
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=26899568
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=27102241
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=27689343
17.
18. Rechner AR, Spencer JP, Kuhnle G, Hahn U, Rice-Evans CA: Novel biomarkers of the metabolism of caffeic acid derivatives in vivo. Free Radic Biol Med. 2001 Jun 1;30(11):1213-22.
19. Redeuil K, Smarrito-Menozzi C, Guy P, Rezzi S, Dionisi F, Williamson G, Nagy K, Renouf M: Identification of novel circulating coffee metabolites in human plasma by liquid chromatography-mass spectrometry. J Chromatogr A. 2011 Jul 22;1218(29):4678-88. doi: 10.1016/j.chroma.2011.05.050. Epub 2011 May 26.
20. Ludwig IA, Paz de Pena M, Concepcion C, Alan C: Catabolism of coffee chlorogenic acids by human colonic microbiota. Biofactors. 2013 Nov-Dec;39(6):623-32. doi: 10.1002/biof.1124. Epub 2013 Aug 1.
21. Lang R, Dieminger N, Beusch A, Lee YM, Dunkel A, Suess B, Skurk T, Wahl A, Hauner H, Hofmann T: Bioappearance and pharmacokinetics of bioactives upon coffee consumption. Anal Bioanal Chem. 2013 Oct;405(26):8487-503. doi: 10.1007/s00216-013-7288-0. Epub 2013 Aug 28.
22. Stalmach A, Williamson G, Crozier A: Impact of dose on the bioavailability of coffee chlorogenic acids in humans. Food Funct. 2014 Aug;5(8):1727-37. doi: 10.1039/c4fo00316k.
23. Wang P, Chen H, Zhu Y, McBride J, Fu J, Sang S: Oat avenanthramide-C (2c) is biotransformed by mice and the human microbiota into bioactive metabolites. J Nutr. 2015 Feb;145(2):239-45. doi: 10.3945/jn.114.206508. Epub 2014 Dec 17.
24. Mills CE, Tzounis X, Oruna-Concha MJ, Mottram DS, Gibson GR, Spencer JP: In vitro colonic metabolism of coffee and chlorogenic acid results in selective changes in human faecal microbiota growth. Br J Nutr. 2015 Apr 28;113(8):1220-7. doi: 10.1017/S0007114514003948. Epub 2015 Mar 26.
25. Tan S, Calani L, Bresciani L, Dall'asta M, Faccini A, Augustin MA, Gras SL, Del Rio D: The degradation of curcuminoids in a human faecal fermentation model. Int J Food Sci Nutr. 2015;66(7):790-6. doi: 10.3109/09637486.2015.1095865.
26. Sanchez-Bridge B, Renouf M, Sauser J, Beaumont M, Actis-Goretta L: The roasting process does not influence the extent of conjugation of coffee chlorogenic and phenolic acids. Biofactors. 2016 May;42(3):259-67. doi: 10.1002/biof.1268. Epub 2016 Feb 22.
27. Vitaglione P, Mennella I, Ferracane R, Rivellese AA, Giacco R, Ercolini D, Gibbons SM, La Storia A, Gilbert JA, Jonnalagadda S, Thielecke F, Gallo MA, Scalfi L, Fogliano V: Whole-grain wheat consumption reduces inflammation in a randomized controlled trial on overweight and obese subjects with unhealthy dietary and lifestyle behaviors: role of polyphenols bound to cereal dietary fiber. Am J Clin Nutr. 2015 Feb;101(2):251-61. doi: 10.3945/ajcn.114.088120. Epub 2014 Dec 3.
28. Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510