FComEx: trans-Ferulic acid (PC000015)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:19 UTC

Update date

2017-01-19 02:36:10 UTC

FoodComEx ID

PC000015

FoodDB Record

FDB012802

Chemical Information

Name

trans-Ferulic acid

Description

Ferulic 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‚Äôs 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 Number

537-98-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate	biospider
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid	biospider
(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	biospider
(E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate	biospider
(E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid	biospider
(E)-4-Hydroxy-3-methoxy-cinnamate	biospider
(E)-4-Hydroxy-3-methoxy-cinnamic acid	biospider
(E)-4-Hydroxy-3-methoxycinnamate	biospider
(E)-4-Hydroxy-3-methoxycinnamic acid	biospider
(e)-4'-Hydroxy-3'-methoxycinnamate	Generator
(E)-4'-Hydroxy-3'-methoxycinnamic acid	biospider
(E)-Ferulate	biospider
(E)-Ferulic acid	biospider
2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, (E)-	biospider
3-(4-Hydroxy-3-methoxyphenyl)propenoate	Generator
3-(4-Hydroxy-3-methoxyphenyl)propenoic acid	ChEBI
3-Methoxy-4-hydroxy-trans-cinnamate	Generator
3-Methoxy-4-hydroxy-trans-cinnamic acid	ChEBI
4-Hydroxy-3-methoxy-(E)-cinnamic acid	biospider
4-Hydroxy-3-methoxycinnamate	Generator
4-Hydroxy-3-methoxycinnamic acid	ChEBI
Ferulate	Generator
trans-4-Hydroxy-3-methoxycinnamate	biospider
trans-4-Hydroxy-3-methoxycinnamic acid	biospider
trans-Ferulate	biospider
trans-Ferulic acid	biospider

Chemical Formula

C10H10O4

IUPAC name

(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

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

Isomeric SMILES

COC1=C(O)C=CC(\C=C\C(O)=O)=C1

Average Molecular Weight

194.184

Monoisotopic Molecular Weight

194.057908808

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents