Common Name(e)-ferulate
Descriptiontrans-Ferulic 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
Molecular FormulaC10H10O4
Average Mass194.18400
Monoisotopic Mass194.05791
IUPAC Name(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
Traditional NameFerulic acid
CAS Registry Number537-98-4
SMILESCOc1cc(/C=C/C(=O)[O-])ccc1O
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
CHEBI IDCHEBI:29749
HMDB IDHMDB0000954
StateSolid
Water Solubility9.06e-01 g/l
logP1.58
logS-2.33
pKa (Strongest Acidic)3.77
pKa (Strongest Basic)-4.89
Hydrogen Acceptor Count4
Hydrogen Donor Count2
Polar Surface Area66.76 Ų
Rotatable Bond Count3
Physiological Charge-1
Formal Charge0
Refractivity51.50 m³·mol⁻¹
Polarizability19.18

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