You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-09-22 21:06:32 UTC
HMDB IDHMDB00954
Secondary Accession Numbers
  • HMDB00537
Metabolite Identification
Common Nametrans-Ferulic acid
Descriptiontrans-Ferulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. trans-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 (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 reduce oxidative damage and amyloid pathology in Alzheimer disease. (PMID: 17127365 , 1398220 , 15453708 , 9878519 ).
Structure
Thumb
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
trans-Ferulic acidChEBI
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoateGenerator
(e)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoateGenerator
(e)-4'-Hydroxy-3'-methoxycinnamateGenerator
(e)-4-Hydroxy-3-methoxycinnamateGenerator
(e)-FerulateGenerator
3-(4-Hydroxy-3-methoxyphenyl)propenoateGenerator
3-Methoxy-4-hydroxy-trans-cinnamateGenerator
4-Hydroxy-3-methoxycinnamateGenerator
trans-4-Hydroxy-3-methoxycinnamateGenerator
trans-FerulateGenerator
(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
FerulateHMDB
Ferulic 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 KeyInChIKey=KSEBMYQBYZTDHS-HWKANZROSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxycinnamic acids. These 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
  • Hydroxycinnamic acid
  • Coumaric acid or derivatives
  • Cinnamic acid
  • Methoxyphenol
  • Phenylpropene
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Food
  • Microbial
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.5 m3·mol-1ChemAxon
Polarizability19.18 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-05g4-1978000000-1097d5b300514a0489dfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00kv-2964000000-3d20d62c97c33247cfcfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00ku-1965000000-ebee2a916fe97f0270a1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9654000000-b3f1759076cffd2ac235View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-000m-3975000000-5a41c311d78f7219474cView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-d193da7a6efffdab2dbbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-7900000000-b5b8d28b28c8067c3932View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002r-9000000000-d3616a5367a7a2a9b3c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0006-1900000000-5dffac87fe7c815de4ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-c173873ef0d975be6c34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-0b9174ecaba08b2f01b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-1900000000-eff77e27aef254928643View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001r-9700000000-18946fad05ffb1f78a7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001r-9300000000-e2221a73d3d078bf6e03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-653c9a454414dd8b8b50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-002b-0900000000-62b2ee8bf9571be3d97fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-a7cded21e6010eb8bce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-8c81de6c352294475072View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Fibroblasts
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified8.549 +/- 0.978 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified11.793 +/- 6.952 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified13.801 +/- 11.844 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified13.853 +/- 11.0720 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedBoth
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 QuantifiedNot ApplicableAdult (>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 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
BiofluidStatusValueAgeSexConditionReferenceDetails
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 QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot ApplicableAdult (>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
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID499
Phenol Explorer Metabolite ID459
FoodDB IDFDB012802
KNApSAcK IDNot Available
Chemspider ID393368
KEGG Compound IDC01494
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFerulic acid
NuGOwiki LinkHMDB00954
Metagene LinkHMDB00954
METLIN ID4156
PubChem Compound445858
PDB IDFER
ChEBI ID17620
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. 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. [14709852 ]
  2. Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. [10706426 ]
  3. Schindler AE, Siiteri PK: Isolation and quantitation of steroids from normal human amniotic fluid. J Clin Endocrinol Metab. 1968 Aug;28(8):1189-98. [4234060 ]
  4. 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. [15309442 ]
  5. 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. [10051848 ]
  6. Tringali C, Spatafora C, Longo OD: Bioactive constituents of the bark of Parkia biglobosa. Fitoterapia. 2000 Apr;71(2):118-25. [10727806 ]
  7. 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. [10794925 ]
  8. 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. [15374625 ]
  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. [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. [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. [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. [17127365 ]
  13. Graf E: Antioxidant potential of ferulic acid. Free Radic Biol Med. 1992 Oct;13(4):435-48. [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. [15453708 ]
  15. Bourne LC, Rice-Evans C: Bioavailability of ferulic acid. Biochem Biophys Res Commun. 1998 Dec 18;253(2):222-7. [9878519 ]