Record Information
Version1.0
Creation date2015-10-09 22:27:19 UTC
Update date2017-01-19 02:36:10 UTC
FoodComEx IDPC000015
FoodDB RecordFDB012802
Chemical Information
Nametrans-Ferulic acid
DescriptionFerulic acid, also known as (e)-ferulate or trans-ferulate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing a cinnamic acid where the benzene ring is hydroxylated. Ferulic acid is a moderately weak acid (based on its pKa). Ferulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. In humans it can be readily 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 kernels. 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 a variety of plant proteins. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), ferulic acid 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’s disease (PMID: 17127365, 1398220, 15453708, 9878519). Ferulic acid can be produced by a number of microbes including Pseudomonas and Saccharomyces (PMID: 8395165). It possesses antioxidant, anti-aging and anti-inflammatory properties. It protects the skin from damage by UV light and is used in skin care, sun care, hair care and color cosmetics.
CAS Number537-98-4
Structure
Thumb
Synonyms
SynonymSource
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoatebiospider
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidbiospider
(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acidbiospider
(E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoatebiospider
(E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidbiospider
(E)-4-Hydroxy-3-methoxy-cinnamatebiospider
(E)-4-Hydroxy-3-methoxy-cinnamic acidbiospider
(E)-4-Hydroxy-3-methoxycinnamatebiospider
(E)-4-Hydroxy-3-methoxycinnamic acidbiospider
(e)-4'-Hydroxy-3'-methoxycinnamateGenerator
(E)-4'-Hydroxy-3'-methoxycinnamic acidbiospider
(E)-Ferulatebiospider
(E)-Ferulic acidbiospider
2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, (E)-biospider
3-(4-Hydroxy-3-methoxyphenyl)propenoateGenerator
3-(4-Hydroxy-3-methoxyphenyl)propenoic acidChEBI
3-Methoxy-4-hydroxy-trans-cinnamateGenerator
3-Methoxy-4-hydroxy-trans-cinnamic acidChEBI
4-Hydroxy-3-methoxy-(E)-cinnamic acidbiospider
4-Hydroxy-3-methoxycinnamateGenerator
4-Hydroxy-3-methoxycinnamic acidChEBI
FerulateGenerator
trans-4-Hydroxy-3-methoxycinnamatebiospider
trans-4-Hydroxy-3-methoxycinnamic acidbiospider
trans-Ferulatebiospider
trans-Ferulic acidbiospider
Chemical FormulaC10H10O4
IUPAC name(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C(O)C=CC(\C=C\C(O)=O)=C1
Average Molecular Weight194.184
Monoisotopic Molecular Weight194.057908808
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP1.51HANSCH,C ET AL. (1995)
Experimental Water SolubilityNot Available
Melting PointMp 174°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 8 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Glentham GK2300
Toronto Research Chemicals F308895