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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:37 UTC
HMDB IDHMDB0000954
Secondary Accession Numbers
  • HMDB0000537
  • HMDB00537
  • HMDB00954
Metabolite Identification
Common NameFerulic acid
DescriptionFerulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. Ferulic acid is a phenolic acid that can be absorbed by the small intestine and excreted through the urine. It is one of the most abundant phenolic acids in plants, varying from 5 g/kg in wheat bran to 9 g/kg in sugar-beet pulp and 50 g/kg in corn kernel. It occurs primarily in seeds and leaves both in its free form (albeit rarely) and covalently linked to lignin and other biopolymers. It is usually found as ester cross-links with polysaccharides in the cell wall, such as arabinoxylans in grasses, pectin in spinach and sugar beet, and xyloglucans in bamboo. It also can cross-link with proteins. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), it readily forms a resonance-stabilized phenoxy radical which accounts for its potent antioxidant potential. Food supplementation with curcumin and ferulic acid is considered a nutritional approach to reducing oxidative damage and amyloid pathology in Alzheimer disease (PMID: 17127365 , 1398220 , 15453708 , 9878519 ). Ferulic acid can be found in Pseudomonas and Saccharomyces (PMID: 8395165 ).
Structure
Data?1563860677
Synonyms
ValueSource
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidChEBI
(e)-4'-Hydroxy-3'-methoxycinnamic acidChEBI
(e)-4-Hydroxy-3-methoxycinnamic acidChEBI
(e)-Ferulic acidChEBI
3-(4-Hydroxy-3-methoxyphenyl)propenoic acidChEBI
3-Methoxy-4-hydroxy-trans-cinnamic acidChEBI
4-Hydroxy-3-methoxycinnamic acidChEBI
trans-4-Hydroxy-3-methoxycinnamic acidChEBI
Ferulic acidKegg
3-Methoxy-4-hydroxy-trans-cinnamateKegg
4-Hydroxy-3-methoxycinnamateKegg
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoateGenerator
(e)-4'-Hydroxy-3'-methoxycinnamateGenerator
(e)-4-Hydroxy-3-methoxycinnamateGenerator
(e)-FerulateGenerator
3-(4-Hydroxy-3-methoxyphenyl)propenoateGenerator
trans-4-Hydroxy-3-methoxycinnamateGenerator
FerulateGenerator
trans-FerulateGenerator
8,8'-Diferulic acidHMDB
Ferulic acid, (e)-isomerHMDB
Ferulic acid, monosodium saltHMDB
Sodium ferulateHMDB
Ferulic acid, (Z)-isomerHMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoateHMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidHMDB
(e)-4-Hydroxy-3-methoxy-cinnamateHMDB
(e)-4-Hydroxy-3-methoxy-cinnamic acidHMDB
trans-Ferulic acidChEBI
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-acrylic acidHMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acidHMDB
(E)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acidHMDB
Fumalic acidHMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidHMDB
3-(4-Hydroxy-3-methoxyphenyl)acrylic acidHMDB
3-Methoxy-4-hydroxycinnamic acidHMDB
4'-Hydroxy-3'-methoxycinnamic acidHMDB
Coniferic acidHMDB
Ferulaic acidHMDB
Chemical FormulaC10H10O4
Average Molecular Weight194.184
Monoisotopic Molecular Weight194.057908808
IUPAC Name(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
Traditional Nameferulic acid
CAS Registry Number537-98-4
SMILES
COC1=C(O)C=CC(\C=C\C(O)=O)=C1
InChI Identifier
InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
InChI KeyKSEBMYQBYZTDHS-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-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 Point168 - 171 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.51HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP1.58ALOGPS
logP1.67ChemAxon
logS-2.3ALOGPS
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
Polarizability19.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-05g4-1978000000-1097d5b300514a0489dfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00kv-2964000000-3d20d62c97c33247cfcfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00ku-1965000000-ebee2a916fe97f0270a1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9654000000-b3f1759076cffd2ac235JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-000m-3975000000-5a41c311d78f7219474cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-5dffac87fe7c815de4ceJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2900000000-8db541bacfe47b9e0c8bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2900000000-a338415bd30d4e62e664JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05g4-1978000000-1097d5b300514a0489dfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kv-2964000000-3d20d62c97c33247cfcfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ku-1965000000-ebee2a916fe97f0270a1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9654000000-b3f1759076cffd2ac235JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000m-3975000000-5a41c311d78f7219474cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kv-1954000000-9dae07505bd18466be87JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-0900000000-d76b7991f2d90cb58bd5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-6094000000-b805979df23a0d890d7cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-d193da7a6efffdab2dbbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-7900000000-b5b8d28b28c8067c3932JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002r-9000000000-d3616a5367a7a2a9b3c6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0006-1900000000-5dffac87fe7c815de4ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-c173873ef0d975be6c34JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-0b9174ecaba08b2f01b9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-1900000000-eff77e27aef254928643JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001r-9700000000-18946fad05ffb1f78a7dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001r-9300000000-e2221a73d3d078bf6e03JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-653c9a454414dd8b8b50JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-002b-0900000000-62b2ee8bf9571be3d97fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-a7cded21e6010eb8bce2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-c173873ef0d975be6c34JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-0b9174ecaba08b2f01b9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-eff77e27aef254928643JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-9700000000-18946fad05ffb1f78a7dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-9300000000-e2221a73d3d078bf6e03JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-a7cded21e6010eb8bce2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-002b-0900000000-cdced9ddbcdaedf2f1b9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-434fdd914ca34cd68f41JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0dcbcad8bf6cb403f4f8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g31-5900000000-4fa9ed831b4e0d1573e5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-29c8691e15490f8d88acJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e940f09e099b7acf3772JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o1-1900000000-ee61087a069406e459c7JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-8c81de6c352294475072JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
  • Stratum Corneum
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.053 +/- 0.017 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.031 +/- 0.011 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.052 +/- 0.02 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.13 +/- 0.054 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.027 +/- 0.005 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.031 +/- 0.008 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.029 +/- 0.004 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.157 +/- 0.129 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.039 +/- 0.020 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0-1.581 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected and Quantified8.549 +/- 0.978 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified11.793 +/- 6.952 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified13.801 +/- 11.844 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified13.853 +/- 11.0720 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedBoth
Normal
details
FecesDetected and Quantified0.340 (0.00515-5.0210) nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.80-1.3 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified5.626 +/- 2.711 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified36.3 +/- 11.2 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.78-0.98 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified2.814 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.376-9.270 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.364 +/- 0.108 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.481 +/- 0.188 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified3.557 +/- 2.039 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.5 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.2 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.245 +/- 0.061 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified1 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified10.181 +/- 5.131 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified22.261 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected but not Quantified Adult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not Quantified Adult (>18 years old)Both
Hypertension (mild)
details
UrineDetected and Quantified4.18 +/- 3.519 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB07767
Phenol Explorer Compound ID499
FoodDB IDFDB012802
KNApSAcK IDC00002743
Chemspider ID393368
KEGG Compound IDC01494
BioCyc IDFERULIC-ACID
BiGG IDNot Available
Wikipedia LinkFerulic_Acid
METLIN ID4156
PubChem Compound445858
PDB IDNot Available
ChEBI ID17620
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceOu, Shiyi; Zhang, Jing; Bao, Huiyan; Zhang, Ning; Li, Aijun. Method for preparing oligosaccharide and trans-ferulic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 8 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Schindler AE, Siiteri PK: Isolation and quantitation of steroids from normal human amniotic fluid. J Clin Endocrinol Metab. 1968 Aug;28(8):1189-98. [PubMed:4234060 ]
  2. Harder H, Tetens I, Let MB, Meyer AS: Rye bran bread intake elevates urinary excretion of ferulic acid in humans, but does not affect the susceptibility of LDL to oxidation ex vivo. Eur J Nutr. 2004 Aug;43(4):230-6. Epub 2004 Jan 6. [PubMed:15309442 ]
  3. Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. [PubMed:10706426 ]
  4. Choudhary G, Chakel J, Hancock W, Torres-Duarte A, McMahon G, Wainer I: Investigation of the potential of capillary electrophoresis with off-line matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for clinical analysis: examination of a glycoprotein factor associated with cancer cachexia. Anal Chem. 1999 Feb 15;71(4):855-9. [PubMed:10051848 ]
  5. Tringali C, Spatafora C, Longo OD: Bioactive constituents of the bark of Parkia biglobosa. Fitoterapia. 2000 Apr;71(2):118-25. [PubMed:10727806 ]
  6. Saija A, Tomaino A, Trombetta D, De Pasquale A, Uccella N, Barbuzzi T, Paolino D, Bonina F: In vitro and in vivo evaluation of caffeic and ferulic acids as topical photoprotective agents. Int J Pharm. 2000 Apr 10;199(1):39-47. [PubMed:10794925 ]
  7. Kang J, Liu Y, Xie MX, Li S, Jiang M, Wang YD: Interactions of human serum albumin with chlorogenic acid and ferulic acid. Biochim Biophys Acta. 2004 Sep 24;1674(2):205-14. [PubMed:15374625 ]
  8. Homma K, Hasegawa T, Masumoto M, Takeshita E, Watanabe K, Chiba H, Kurosawa T, Takahashi T, Matsuo N: Reference values for urinary steroids in Japanese newborn infants: gas chromatography/mass spectrometry in selected ion monitoring. Endocr J. 2003 Dec;50(6):783-92. [PubMed:14709852 ]
  9. Baba S, Osakabe N, Natsume M, Yasuda A, Muto Y, Hiyoshi K, Takano H, Yoshikawa T, Terao J: Absorption, metabolism, degradation and urinary excretion of rosmarinic acid after intake of Perilla frutescens extract in humans. Eur J Nutr. 2005 Feb;44(1):1-9. Epub 2004 Feb 18. [PubMed:15309457 ]
  10. Tapia A, Rodriguez J, Theoduloz C, Lopez S, Feresin GE, Schmeda-Hirschmann G: Free radical scavengers and antioxidants from Baccharis grisebachii. J Ethnopharmacol. 2004 Dec;95(2-3):155-61. [PubMed:15507329 ]
  11. Trombino S, Serini S, Di Nicuolo F, Celleno L, Ando S, Picci N, Calviello G, Palozza P: Antioxidant effect of ferulic acid in isolated membranes and intact cells: synergistic interactions with alpha-tocopherol, beta-carotene, and ascorbic acid. J Agric Food Chem. 2004 Apr 21;52(8):2411-20. [PubMed:15080655 ]
  12. Mancuso C, Scapagini G, Curro D, Giuffrida Stella AM, De Marco C, Butterfield DA, Calabrese V: Mitochondrial dysfunction, free radical generation and cellular stress response in neurodegenerative disorders. Front Biosci. 2007 Jan 1;12:1107-23. [PubMed:17127365 ]
  13. Graf E: Antioxidant potential of ferulic acid. Free Radic Biol Med. 1992 Oct;13(4):435-48. [PubMed:1398220 ]
  14. Fukuoka K, Sawabe A, Sugimoto T, Koga M, Okuda H, Kitayama T, Shirai M, Komai K, Komemushi S, Matsuda K: Inhibitory actions of several natural products on proliferation of rat vascular smooth muscle cells induced by Hsp60 from Chlamydia pneumoniae J138. J Agric Food Chem. 2004 Oct 6;52(20):6326-9. [PubMed:15453708 ]
  15. Bourne LC, Rice-Evans C: Bioavailability of ferulic acid. Biochem Biophys Res Commun. 1998 Dec 18;253(2):222-7. [PubMed:9878519 ]
  16. Huang Z, Dostal L, Rosazza JP: Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens. Appl Environ Microbiol. 1993 Jul;59(7):2244-50. [PubMed:8395165 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Ferulic acid → 6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Ferulic acid → 3,4,5-trihydroxy-6-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Ferulic acid → Ferulic acid 4-O-sulfatedetails