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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:28 UTC
HMDB IDHMDB0000955
Secondary Accession Numbers
  • HMDB00955
Metabolite Identification
Common NameIsoferulic acid
DescriptionIsoferulic acid (CAS: 537-73-5) is a chlorogenic acid (CGA). CGAs are formed by the esterification of hydroxycinnamic acids (e.g. caffeic acid, ferulic acid, and p-coumaric acid) with quinic acid. CGAs are abundant phenolic compounds in coffee, with caffeoylquinic (CQA), feruloylquinic (FQA), and dicaffeoylquinic (diCQA) acids being the major subclasses, and coffee is the most consumed food product in the world. Isoferulic acid is present in normal human urine in concentrations of 0.05-2.07 umol/mmol creatinine at baseline, and reaches 0.2-9.6 umol/mmol creatinine in four hours after a cup of coffee, with a large inter-individual variation (PMID:17884997 ).
Structure
Data?1601256882
Synonyms
ValueSource
3-Hydroxy-4-methoxycinnamic acidChEBI
Hesperetic acidChEBI
3-Hydroxy-4-methoxycinnamateGenerator
IsoferulateGenerator
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoateHMDB
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acidHMDB
3-Hydroxy-4-methoxy-cinnamateHMDB
3-Hydroxy-4-methoxy-cinnamic acidHMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acidHMDB
(E)-3-Hydroxy-4-methoxycinnamic acidHMDB
(E)-4-Methoxycaffeic acidHMDB
(E)-4-O-Methylcaffeic acidHMDB
(E)-Hesperetic acidHMDB
(E)-Isoferulic acidHMDB
4-Methoxycaffeic acidHMDB
4-O-Methylcaffeic acidHMDB
trans-3-Hydroxy-4-methoxycinnamic acidHMDB
trans-4-Methoxycaffeic acidHMDB
trans-4-O-Methylcaffeic acidHMDB
trans-Hesperetic acidHMDB
trans-Isoferulic acidHMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoateGenerator, HMDB
3'-Hydroxy-4'-methoxycinnamic acidHMDB
(E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoic acidPhytoBank
(2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acidHMDB
Chemical FormulaC10H10O4
Average Molecular Weight194.184
Monoisotopic Molecular Weight194.057908808
IUPAC Name(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
Traditional Nameisoferulic acid
CAS Registry Number25522-33-2
SMILES
COC1=C(O)C=C(\C=C\C(O)=O)C=C1
InChI Identifier
InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
InChI KeyQURCVMIEKCOAJU-HWKANZROSA-N
Chemical Taxonomy
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
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • 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

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point228 - 233 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.87 g/LALOGPS
logP1.56ALOGPS
logP1.67ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.5 m³·mol⁻¹ChemAxon
Polarizability19.36 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available31661259
DarkChem[M-H]-PredictedNot Available31661259
AllCCS[M+H]+PredictedNot Available142.11632859911
AllCCS[M-H]-PredictedNot Available141.26232859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Isoferulic acid,1TMS,#12026.7467https://arxiv.org/abs/1905.12712
Isoferulic acid,1TMS,#22046.3246https://arxiv.org/abs/1905.12712
Isoferulic acid,2TMS,#12081.569https://arxiv.org/abs/1905.12712
Isoferulic acid,1TBDMS,#12319.4841https://arxiv.org/abs/1905.12712
Isoferulic acid,1TBDMS,#22311.4558https://arxiv.org/abs/1905.12712
Isoferulic acid,2TBDMS,#12604.981https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-0900000000-b51b390a0727d3838cab2017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-7094000000-6021a908fd1b4eec8f002017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-db5f99d89dd9e349c86c2015-03-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004l-0900000000-ab3320c9d0dfcba00b6e2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-0900000000-2b9775043a4af5fdc0642012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-0900000000-29fd32eacfaa527045592012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-d26e8f9f43c25710a04d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-003r-0900000000-25d10f2b53d4679375242012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-0900000000-b2f1dd5274585c5f6b0b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-3900000000-2e21dbcbb598dba645252012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-2900000000-7a28000b74f8c4f5b27f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0900000000-623ecba5385a03e0406b2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0900000000-205ebeb435685d894bcf2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0900000000-97eb2cfc1a86c4933f762017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-001i-0900000000-49f1d1fd82311df297132017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-eaa8fbddbddb5c585ea42017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-1900000000-c2fa54dcd41f9ab16b8e2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fs-5900000000-a969ea13d0a4ad63b2a62017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-6b2f8b891907a56146d62017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-6139186c0691cc7b95bb2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-2900000000-8d4f500b0c438df01f412017-06-28View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)2015-03-12View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.128 +/- 0.018 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.126 +/- 0.028 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.169 +/- 0.03 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.187 +/- 0.048 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.105 +/- 0.021 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.083 +/- 0.01 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.118 +/- 0.016 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.549 +/- 1.451 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected and Quantified18.591 +/- 1.0814 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified21.835 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified21.989 +/- 5.304 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0402 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0572 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
UrineDetected and Quantified0.394 +/- 0.075 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07109
Phenol Explorer Compound ID485
FooDB IDFDB002700
KNApSAcK IDC00002752
Chemspider ID643318
KEGG Compound IDC10470
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsoferulic acid
METLIN ID5901
PubChem Compound736186
PDB IDNot Available
ChEBI ID27794
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceMauthner, P. New synthesis of isoferulic acid. Journal fuer Praktische Chemie (Leipzig) (1922), 104 132-6.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kern SM, Bennett RN, Needs PW, Mellon FA, Kroon PA, Garcia-Conesa MT: Characterization of metabolites of hydroxycinnamates in the in vitro model of human small intestinal epithelium caco-2 cells. J Agric Food Chem. 2003 Dec 31;51(27):7884-91. [PubMed:14690369 ]
  2. Wittemer SM, Ploch M, Windeck T, Muller SC, Drewelow B, Derendorf H, Veit M: Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans. Phytomedicine. 2005 Jan;12(1-2):28-38. [PubMed:15693705 ]
  3. 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. [PubMed:11368919 ]
  4. Hodgson JM, Chan SY, Puddey IB, Devine A, Wattanapenpaiboon N, Wahlqvist ML, Lukito W, Burke V, Ward NC, Prince RL, Croft KD: Phenolic acid metabolites as biomarkers for tea- and coffee-derived polyphenol exposure in human subjects. Br J Nutr. 2004 Feb;91(2):301-6. [PubMed:14756917 ]
  5. Wittemer SM, Veit M: Validated method for the determination of six metabolites derived from artichoke leaf extract in human plasma by high-performance liquid chromatography-coulometric-array detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Aug 15;793(2):367-75. [PubMed:12906912 ]
  6. Stromeier S, Petereit F, Nahrstedt A: Phenolic esters from the rhizomes of Cimicifuga racemosa do not cause proliferation effects in MCF-7 cells. Planta Med. 2005 Jun;71(6):495-500. [PubMed:15971118 ]
  7. Monteiro M, Farah A, Perrone D, Trugo LC, Donangelo C: Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans. J Nutr. 2007 Oct;137(10):2196-201. [PubMed:17884997 ]