Ferulic acid
IUPAC name (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acid
Other names 2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)- ferulic acid 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 3-methoxy-4-hydroxycinnamic acid 4-hydroxy-3-methoxycinnamic acid (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid Ferulate Coniferic acid trans-ferulic acid (E)-ferulic acid
Identifiers
CAS number	1135-24-6 Y
PubChem	445858
ChemSpider	393368 Y
DrugBank	DB07767
ChEBI	CHEBI:17620 Y
ChEMBL	CHEMBL32749 Y
Jmol-3D images	Image 1
SMILES COc1cc(ccc1O)/C=C/C(=O)O
InChI 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+ Y Key: KSEBMYQBYZTDHS-HWKANZROSA-N Y 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+ Key: KSEBMYQBYZTDHS-HWKANZROBE
Properties
Molecular formula	C10H10O4
Molar mass	194.18 g/mol
Melting point	168–172 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 the genus Ferula, referring to the giant fennel (Ferula communis).

Occurrence in nature[link]

Ferulic acid is one of the component of asafoetida, the dried latex from the giant fennel (Ferula communis).

Apart from the giant fennel, 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). Açaí oil, obtained from the fruit of the açaí palm (Euterpe oleracea), is rich in ferulic acid (101 +/- 5.9 mg/kg).^[1]

In cereals, ferulic acid is localized in the bran the hard outer layer of grain. In wheat, phenolic compounds are mainly found in the form of insoluble bound ferulic acid and be relevant to resistance to wheat fungal diseases.^[2]

Asterid Eudicot plants can also produce ferulic acid. The tea brewed from the leaves of yacón (Smallanthus sonchifolius), a traditionally grown in the Northern and Central Andes, contains quantities of ferulic acid, as well as the tea brewed from the European centaury (Centaurium erythraea), a plant used as a medical herb in many parts of Europe.^[3] In legumes, the white bean variety navy bean is the richest source of ferulic acid among the common bean (Phaseolus vulgaris) varieties.^[4] It is also found in horse grams (Macrotyloma uniflorum).^[5]

In processed foods[link]

Cooked sweet corn releases increased levels of ferulic acid.^[6] The compound is also found in rice bran oil, a popular cooking oil in several Asian countries.^[7]

Ferulic acid glucoside can be found in commercial breads containing flaxseed.^[8] Rye bread contains ferulic acid dehydrodimers.^[9]

Metabolism[link]

In plants, ferulic acid (right) is derived from phenylalanine, which is converted to 4-hydroxycinnamic acid (left) and then caffeic acid.

Biosynthesis[link]

Biosynthesis of ferulic acid is by the action of the enzyme caffeate O-methyltransferase.^[1] It is biosynthesized 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.^[10]

It is an intermediate in the synthesis of monolignols, i.e., the monomers of lignin, and is also used for the synthesis of lignans.

Biodegradation[link]

Ferulic acid is converted by certain strains of yeast, notably strains used in brewing of wheat beers, such as Saccharomyces delbrueckii (Torulaspora_delbrueckii), to 4-vinyl guaiacol (2-methoxy-4-vinylphenol) which gives beers such as Weissbier and Wit their distinctive "clove" flavour. Saccharomyces cerevisiae (dry baker's yeast) and Pseudomonas fluorescens are also able to convert trans-ferulic acid into 2-methoxy-4-vinylphenol.^[11] In P. fluorescens, a ferulic acid decarboxylase has been isolated.^[12]

Ecology[link]

Ferulic acid is one of the possible plant compounds that initiate Agrobacterium tumefaciens to infect plant cells.

Extraction[link]

It can be extracted from wheat bran and maize bran using concentrated alkali^[13].

Bio-medical considerations[link]

UV visible spectrum of ferulic acid, with lambda max at 321 and a shoulder at 278 nm

Ferulic acid, like many natural 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] There is also a small amount of research showing oral supplements of ferulic acid can inhibit melanin production in the process of skin whitening.^[14]

Other applications[link]

As a precursor to vanillin[link]

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.

Mass spectrometry[link]

It is used as a matrix for proteins in MALDI mass spectrometry analyses.^[9]

Bitterness masker[link]

Kraft Foods has patented the use of sodium ferulate to mask the bitter aftertaste of the artificial sweetener acesulfame potassium.^[15]

See also[link]

• Caffeic acid
• Coumaric acid
• Diferulic acids

References[link]

Notes[link]

1. ^a Shahadi, Fereidoon; Naczk, Marian (2004). Phenolics in food and nutraceuticals. Florida, USA: CRC Press LLC. p. 4. ISBN 1-58716-138-9. 
2. ^a Kampa, M.; Alexaki, V. I.; Notas, G.; Nifli, A. P.; Nistikaki, A.; Hatzoglou, A.; Bakogeorgou, E.; Kouimtzoglou, E. et al. (2004). "Antiproliferative and apoptotic effects of selective phenolic acids on T47D human breast cancer cells: Potential mechanisms of action". Breast Cancer Research 6 (2): R63–R74. DOI:10.1186/bcr752. PMC 400651. PMID 14979919. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=400651.  edit
3. ^{a b} Lee, Y. S. (2005). "Role of NADPH oxidase-mediated generation of reactive oxygen species in the mechanism of apoptosis induced by phenolic acids in HepG2 human hepatoma cells". Archives of pharmacal research 28 (10): 1183–1189. PMID 16276977.  edit
4. ^a Lesca, P. (1983). "Protective effects of ellagic acid and other plant phenols on benzoapyrene-induced neoplasia in mice". Carcinogenesis 4 (12): 1651–1653. PMID 6317220.  edit
5. ^a Mori, H.; Kawabata, K.; Yoshimi, N.; Tanaka, T.; Murakami, T.; Okada, T.; Murai, H. (1999). "Chemopreventive effects of ferulic acid on oral and rice germ on large bowel carcinogenesis". Anticancer research 19 (5A): 3775–3778. PMID 10625957.  edit
6. ^a Lin, F. H.; Lin, J. Y.; Gupta, R. D.; Tournas, J. A.; Burch, J. A.; Selim, M. A.; Monteiro-Riviere, N. A.; Grichnik, J. M. et al. (2005). "Ferulic Acid Stabilizes a Solution of Vitamins C and E and Doubles its Photoprotection of Skin". Journal of Investigative Dermatology 125 (4): 826–832. DOI:10.1111/j.0022-202X.2005.23768.x. PMID 16185284.  edit
7. ^a Mathew, S.; Abraham, T. E. (2004). "Ferulic Acid: An Antioxidant Found Naturally in Plant Cell Walls and Feruloyl Esterases Involved in its Release and Their Applications". Critical Reviews in Biotechnology 24 (2–3): 59–83. DOI:10.1080/07388550490491467. PMID 15493526.  edit
8. ^a Priefert, H.; Rabenhorst, J.; Steinbüchel, A. (2001). "Biotechnological production of vanillin". Applied microbiology and biotechnology 56 (3–4): 296–314. PMID 11548997.  edit
9. ^a Beavis, R. C.; Chait, B. T.; Fales, H. M. (1989). "Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins". Rapid Communications in Mass Spectrometry 3 (12): 432–435. DOI:10.1002/rcm.1290031207. PMID 2520223.  edit
10. Catherine Tomaro-Duchesneau, Shyamali Saha, Meenakshi Malhotra, Michael Coussa-Charley, Imen Kahouli, Mitchell L. Jones, Alain Labbe, Satya Prakash (2012). "Probiotic Ferulic Acid Esterase Active Lactobacillus fermentum NCIMB 5221 APA Microcapsules for Oral Delivery: Preparation and in Vitro Characterization". Pharmaceuticals. 5 (2): 236–248. DOI:10.3390/ph5020236.