| Ferulic acid | |
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(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acid |
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Other names
2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)- |
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| Identifiers | |
| CAS number | 1135-24-6 |
| PubChem | 445858 |
| ChemSpider | 393368 |
| DrugBank | DB07767 |
| ChEBI | CHEBI:17620 |
| ChEMBL | CHEMBL32749 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C10H10O4 |
| Molar mass | 194.18 g/mol |
| Exact mass | 194.057909 u |
| Melting point |
168–172 °C |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Ferulic acid is a hydroxycinnamic acid, a type of organic compound. It is an abundant phenolic phytochemical found in plant cell wall components such as arabinoxylans as covalent side chains. It is related to trans-cinnamic acid. As a component of lignin, ferulic acid is a precursor in the manufacture of other aromatic compounds. The etymology is from Ferula, referring to the giant fennel (Ferula communis).
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Ferulic acid is found in the seeds of coffee, apple, artichoke, peanut, and orange, as well as in both seeds and cell walls of commelinid plants (such as rice, wheat, oats, and pineapple). It can be extracted from wheat bran and maize bran using concentrated alkali.
Açaí oil, obtained from the fruit of the açaí palm (Euterpe oleracea), is rich in ferulic acid (101 +/- 5.9 mg/kg).[1]
Biosynthesis of ferulic acid is by the action of the enzyme O-methyl transferase on caffeic acid.[1]It is biosynthesised from caffeic acid.
Ferulic acid, together with dihydroferulic acid, is a component of lignocellulose, serving to crosslink the lignin and polysaccharides, thereby conferring rigidity to the cell walls.[2]
It is an intermediate in the synthesis of monolignols, i.e., the monomers of lignin, and is also used for the synthesis of lignans.
Ferulic acid is converted by certain strains of yeast (notably strains of yeast used in brewing of wheat beers, such as Saccharomyces delbrueckii) to 4-vinyl guaiacol which gives beers such as Weissbier and Wit their distinctive "clove" flavour.
Ferulic acid, like many phenols, is an antioxidant in vitro in the sense that it is reactive toward free radicals such as reactive oxygen species (ROS). ROS and free radicals are implicated in DNA damage, cancer, accelerated cell aging. Animal studies and in vitro studies suggest that ferulic acid may have direct antitumor activity against breast cancer[2] and liver cancer.[3] Ferulic acid may have pro-apoptotic effects in cancer cells, thereby leading to their destruction.[3] Ferulic acid may be effective at preventing cancer induced by exposure to the carcinogenic compounds benzopyrene[4] and 4-nitroquinoline 1-oxide.[5] Note that these are not randomized controlled trials done with human participants, and therefore, the results of these studies may not be directly applicable to human use.
If added to a topical preparation of ascorbic acid and vitamin E, ferulic acid may reduce oxidative stress and formation of thymine dimers in skin.[6]
Ferulic acid, being highly abundant, may be useful as a precursor in the manufacturing of vanillin, a synthetic flavoring agent often used in place of natural vanilla extract.[7] However, biotechnological processes may be the most efficient method to use ferulic acid as a precursor,[8] and as such, research is still ongoing.
It is used as a matrix for proteins in MALDI mass spectrometry analyses.[9]
Kraft Foods has patented the use of sodium ferulate to mask the bitter aftertaste of the artificial sweetener acesulfame potassium.[3]
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