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Human Metabolome Database Version 3.5

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Showing metabocard for trans-Ferulic acid (HMDB00954)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:39 -0700
HMDB ID HMDB00954
Secondary Accession Numbers
  • HMDB00537
Metabolite Identification
Common Name trans-Ferulic acid
Description trans-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 Link_out, 1398220 Link_out, 15453708 Link_out, 9878519 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate
  2. (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid
  3. (E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate
  4. (E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid
  5. (E)-4-hydroxy-3-methoxy-Cinnamate
  6. (E)-4-hydroxy-3-methoxy-Cinnamic acid
  7. (E)-4-Hydroxy-3-methoxycinnamate
  8. (E)-4-Hydroxy-3-methoxycinnamic acid
  9. (E)-Ferulate
  10. (E)-Ferulic acid
  11. 3-(4-Hydroxy-3-methoxyphenyl)propenoate
  12. 3-(4-Hydroxy-3-methoxyphenyl)propenoic acid
  13. 4-Hydroxy-3-methoxycinnamate
  14. 4-Hydroxy-3-methoxycinnamic acid
  15. Ferulate
  16. Ferulic acid
  17. trans-4-Hydroxy-3-methoxycinnamate
  18. trans-4-Hydroxy-3-methoxycinnamic acid
  19. trans-Ferulate
  20. trans-Ferulic acid
Chemical Formula C10H10O4
Average Molecular Weight 194.184
Monoisotopic Molecular Weight 194.057908808
IUPAC Name (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
Traditional IUPAC Name ferulic acid
CAS Registry Number 537-98-4
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 Key KSEBMYQBYZTDHS-HWKANZROSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Cinnamic Acid Derivatives
Sub Class Hydroxycinnamic Acid Derivatives
Other Descriptors
  • Cinnamic Acid Derivatives
  • Coniferyl alcohol derivatives(KEGG)
  • Coumaric Acid Derivatives
  • Organic Compounds
  • ferulic acids(ChEBI)
  • hydroxycinnamic acid(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Allyl Alcohol
  • Anisole
  • Carboxylic Acid
  • Enone
  • Methoxyphenol
  • Phenol
  • Phenol Derivative
  • Phenylpropene
  • Styrene
Direct Parent Hydroxycinnamic Acid Derivatives
Ontology
Status Detected and Quantified
Origin
  • Food
  • Plant
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 168 - 171 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 1.51 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.91 g/L ALOGPS
LogP 1.58 ALOGPS
LogP 1.67 ChemAxon
LogS -2.33 ALOGPS
pKa (strongest acidic) 3.77 ChemAxon
pKa (strongest basic) -4.9 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.76 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 51.5 ChemAxon
Polarizability 19.18 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-52)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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0.053 +/- 0.017 uM Adult (>18 years old) Male Normal Before ingestion of water
Blood Detected and Quantified
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0.031 +/- 0.011 uM Adult (>18 years old) Male Normal 2 h after ingestion of water
Blood Detected and Quantified
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0.052 +/- 0.02 uM Adult (>18 years old) Male Normal Before ingestion of quercetin
Blood Detected and Quantified
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0.13 +/- 0.054 uM Adult (>18 years old) Male Normal 2 h after ingestion of 200 mg of quercetin
Blood Detected and Quantified
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0.027 +/- 0.005 uM Adult (>18 years old) Male Normal Before ingestion of (-)-epicathechin
Blood Detected and Quantified
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0.031 +/- 0.008 uM Adult (>18 years old) Male Normal 2 h after ingestion of 200 mg of (-)-epicathechin
Blood Detected and Quantified
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0.029 +/- 0.004 uM Adult (>18 years old) Male Normal Before ingestion of epigallocatechin gallate
Blood Detected and Quantified
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0.157 +/- 0.129 uM Adult (>18 years old) Male Normal 2 h after ingestion of 200 mg of...
Blood Detected and Quantified
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0.039 +/- 0.020 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
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36.3 +/- 11.2 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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0.364 +/- 0.108 umol/mmol creatinine Adult (>18 years old) Male Normal Before ingestion of 200 mg of quercetin
Urine Detected and Quantified
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0.481 +/- 0.188 umol/mmol creatinine Adult (>18 years old) Male Normal 5-h after ingestion of 200 mg of quercetin
Urine Detected and Quantified
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0.5 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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1.2 umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
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0.245 +/- 0.061 umol/mmol creatinine Adult (>18 years old) Male Normal 5-h after ingestion of 200 mg of quercetin,...
Urine Detected and Quantified
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1 umol/mmol creatinine Adult (>18 years old) Both Normal by GC-MS
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Hypertension (mild) After 4-wk comsumption of polyphenol-rich MIX....
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Hypertension (mild) After 4-wk comsumption of polyphenol-rich GJX...
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID 499 Link_out
Phenol Explorer Metabolite ID 459 Link_out
FoodDB ID FDB012802
KNApSAcK ID Not Available
Chemspider ID 393368 Link_out
KEGG Compound ID C01494 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Ferulic acid Link_out
NuGOwiki Link HMDB00954 Link_out
Metagene Link HMDB00954 Link_out
METLIN ID 4156 Link_out
PubChem Compound 445858 Link_out
PDB ID FER Link_out
ChEBI ID 17620 Link_out
References
Synthesis Reference Ou, 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  5. Tringali C, Spatafora C, Longo OD: Bioactive constituents of the bark of Parkia biglobosa. Fitoterapia. 2000 Apr;71(2):118-25. Pubmed: 10727806 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out