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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-15 17:04:51 UTC
HMDB IDHMDB0000955
Secondary Accession Numbers
  • HMDB00955
Metabolite Identification
Common NameIsoferulic acid
DescriptionIsoferulic acid, also known as hesperetic acid or hesperetate, 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. Isoferulic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isoferulic acid is found, on average, in the highest concentration within a few different foods, such as sunflowers, common wheats, and vinegars and in a lower concentration in peanuts. Isoferulic acid has also been detected, but not quantified in, a few different foods, such as bilberries, german camomiles, and soy beans. This could make isoferulic acid a potential biomarker for the consumption of these foods. Isoferulic acid (CAS: 537-73-5) is a chlorogenic acid (CGA). 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 ). 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. CGAs are formed by the esterification of hydroxycinnamic acids (e.g. caffeic acid, ferulic acid, and p-coumaric acid) with quinic acid.
Structure
Data?1582752167
Synonyms
ValueSource
3-Hydroxy-4-methoxycinnamic acidChEBI
Hesperetic acidChEBI
3-Hydroxy-4-methoxycinnamateGenerator
HesperetateGenerator
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
Isoferulic acidHMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoateGenerator
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 Properties
PropertyValueReference
Melting Point228 - 233 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-0900000000-b51b390a0727d3838cabSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-7094000000-6021a908fd1b4eec8f00Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004l-0900000000-ab3320c9d0dfcba00b6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-0900000000-2b9775043a4af5fdc064Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-0900000000-29fd32eacfaa52704559Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-d26e8f9f43c25710a04dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-003r-0900000000-25d10f2b53d467937524Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-0900000000-b2f1dd5274585c5f6b0bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-3900000000-2e21dbcbb598dba64525Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-2900000000-7a28000b74f8c4f5b27fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b66Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b66Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0900000000-623ecba5385a03e0406bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0900000000-205ebeb435685d894bcfSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0900000000-97eb2cfc1a86c4933f76Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-001i-0900000000-49f1d1fd82311df29713Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-eaa8fbddbddb5c585ea4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-1900000000-c2fa54dcd41f9ab16b8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fs-5900000000-a969ea13d0a4ad63b2a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-6b2f8b891907a56146d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-6139186c0691cc7b95bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-2900000000-8d4f500b0c438df01f41Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-db5f99d89dd9e349c86cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected but not Quantified Adult (>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 Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 485 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 Quantified Not 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
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 ]