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Bovine Rumen Metabolome Database



Showing metabocard for trans-Ferulic acid (RMDB00954)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-06 16:53:08
Accession Number RMDB00954
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, 1398220, 15453708, 9878519).
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-methoxycinnamate
  6. (E)-4-Hydroxy-3-methoxycinnamic acid
  7. (E)-4-hydroxy-3-methoxy-Cinnamate
  8. (E)-4-hydroxy-3-methoxy-Cinnamic 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. trans-4-Hydroxy-3-methoxycinnamate
  17. trans-4-Hydroxy-3-methoxycinnamic acid
  18. trans-Ferulate
  19. trans-Ferulic acid
  20. Ferulic acid
Chemical IUPAC Name 3-(4-hydroxy-3-methoxyphenyl)-prop-2-enoic acid
Chemical Formula C10H10O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Alcohols
Class
  • Polyphenols
Sub Class
  • Phenolic acids
Family
  • Plant_Metabolite
Species
  • phenol or hydroxyhetarene; alkyl aryl ether ; carboxylic acid; alkene; aromatic compound
Biofunction
Application
Source
  • Exogenous
Average Molecular Weight 194.184
Monoisotopic Molecular Weight 194.057907
Isomeric SMILES COC1=C(O)C=CC(C=CC(O)=O)=C1
Canonical SMILES COC1=C(O)C=CC(C=CC(O)=O)=C1
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Ferulic acid Link Image
METLIN ID 4156 Link Image
PubChem Compound 445858 Link Image
PubChem Substance 36519565 Link Image
ChEBI ID 17620 Link Image
CAS Registry Number 537-98-4
InChI Identifier InChI=1/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+
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.
Melting Point (Experimental) 168-171 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 5.97 mg/mL [MEYLAN,WM et al. (1996)]; 0.906 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity 1.51 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 1.58 [Predicted by ALOGPS]; 1.4 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 1GKL Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from Solubility)
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 17.06 +/- 7.54 uM
Age 4-5 years old
Sex Female (lactating)
Condition Normal (0% barley grain in dry matter (DM) basis)
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 8.1 +/- 5.2 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Burim N. Ametaj, Qendrim Zebeli, Fozia Saleem, Nikolaos Psychogios, Michael J. Lewis, Suzanna M. Dunn, Jianguo Xia and David S. Wishart Metabolomics 2010;6(4):583-594
Concentrations (Abnormal)
Biofluid Rumen
Value 20 +/- 4 uM
Age 4-5 years old
Sex Female (lactating)
Condition 15% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 13 +/- 3 uM
Age 4-5 years old
Sex Female (lactating)
Condition 30% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 20 +/- 11 uM
Age 4-5 years old
Sex Female (lactating)
Condition 45% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image