Ferulic acid

Ferulic acid
Names
Preferred IUPAC name
(2E)-3-(4-hydroxy-3-methoxyphenyl)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
Coniferic acid
trans-ferulic acid
(E)-ferulic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.892 Edit this at Wikidata
UNII
  • 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+ checkY
    Key: KSEBMYQBYZTDHS-HWKANZROSA-N checkY
  • 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
  • COc1cc(ccc1O)/C=C/C(=O)O
Properties
C10H10O4
Molar mass 194.186 g·mol−1
Appearance Crystalline powder
Melting point 168 to 172 °C (334 to 342 °F; 441 to 445 K)
0.78 g/L
Acidity (pKa) 4.61
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ferulic acid is a hydroxycinnamic acid derivative and a phenolic compound. It is an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans. Salts and esters derived from ferulic acid are called ferulates.

Property

Ultraviolet–visible spectrum of ferulic acid, with λmax at 321 nm and a shoulder at 278 nm

Ferulic acid is a reducing agent. The double bond in the side chain is subjected to cis–trans isomerization, and the resonance stabilized phenoxy radical account for its reduction potential.

Occurrence

In plants

First separated in Ferula foetida in 1866, ferulic acid is ubiquitous in the plant kingdom, including a number of vegetable sources. It is commonly found in the cell wall of woods, grasses, and corn hulls. They are usually tightly bound to carbohydrates as a glycosidic conjugate, an ester, or an amide. To extract it, one can apply concentrated alkali to the plant tissue.

Asterid eudicot plants can also produce ferulic acid. The tea brewed from the leaves of yacón (Smallanthus sonchifolius), a plant traditionally grown in the northern and central Andes, contains quantities of ferulic acid. In legumes, the white bean variety navy bean is the richest source of ferulic acid among the common bean (Phaseolus vulgaris) varieties. It is also found in horse grams (Macrotyloma uniflorum).[citation needed]

Although there are many sources of ferulic acid in nature, its bioavailability depends on the form in which it is present: free ferulic acid has limited solubility in water, and hence poor bioavailability. In wheat grain, ferulic acid is found bound to cell wall polysaccharides, allowing it to be released and absorbed in the small intestine.

In processed foods

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 may be relevant to resistance to wheat fungal diseases. It can be extracted from wheat bran and maize bran using concentrated alkali.

The highest known concentration of ferulic acid glucoside has been found in flaxseed (4.1±0.2 g/kg). It is also found in barley grain.

Cooking sweetcorn releases increased levels of ferulic acid. As plant sterol esters, this compound is naturally found in rice bran oil, a popular cooking oil in several Asian countries.

Ferulic acid glucoside can be found in commercial breads containing flaxseed. Rye bread contains ferulic acid dehydrodimers.

It occurs in particularly high concentrations in popcorn (0.31% by weight) and bamboo shoots (0.24%), and sugar beat pulp (0.8%).

Metabolism

In plants, ferulic acid (right) is derived from phenylalanine (not shown), which is converted to 4-hydroxycinnamic acid (left) and then caffeic acid (center).

Biosynthesis

Ferulic acid is biosynthesized in plants from caffeic acid by the action of the enzyme caffeate O-methyltransferase.

In a proposed ferulic acid biosynthetic pathway for Escherichia coli, L-tyrosine is converted to 4-coumaric acid by tyrosine ammonia lyase, which is converted to caffeic acid by Sam5, which is then converted to ferulic acid by caffeic acid methyltransferase.

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.

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

It is a major metabolite of chlorogenic acids in humans along with caffeic and isoferulic acid, and is absorbed in the small intestine, whereas other metabolites such as dihydroferulic acid, feruloylglycine, and dihydroferulic acid are produced from chlorogenic acid in the large intestine by the action of gut flora.

Biodegradation

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-vinylguaiacol (2-methoxy-4-vinylphenol) which gives beers such as Weissbier and Wit their distinctive clove-like flavor. Saccharomyces cerevisiae (dry baker's yeast) and Pseudomonas fluorescens are also able to convert trans-ferulic acid into 4-vinylguaiacol. In P. fluorescens, a ferulic acid decarboxylase has been isolated.

Function

Ferulic acid is one of the compounds that initiate the vir (virulence) region of Agrobacterium tumefaciens, inducing it to infect plant cells.

In cosmetics, ferulic acid is used topically as an ultraviolet light absorber (sunscreen), a treatment for photoaging, and a treatment for skin darkening. The skin absorbs it at the same rate at acidic and neutral pH. It is believed to inhibit melanin formation by competitive inhibition with tyrosine. The oxidation of tyrosine is a necessary step in the formation of melanin.

See also

References

  1. 1 2 Mota, Fátima L.; Queimada, António J.; Pinho, Simão P.; Macedo, Eugénia A. (August 2008). "Aqueous Solubility of Some Natural Phenolic Compounds" (PDF). Industrial & Engineering Chemistry Research. 47 (15): 5182–5189. doi:10.1021/ie071452o. hdl:10198/1506.
  2. 1 2 De Oliveira, Dyoni Matias; Finger-Teixeira, Aline; Rodrigues Mota, Thatiane; Salvador, Victor Hugo; Moreira-Vilar, Flávia Carolina; Correa Molinari, Hugo Bruno; Craig Mitchell, Rowan Andrew; Marchiosi, Rogério; Ferrarese-Filho, Osvaldo; Dantas Dos Santos, Wanderley (2015). "Ferulic acid: A Key Component in Grass Lignocellulose Recalcitrance to Hydrolysis". Plant Biotechnology Journal. 13 (9): 1224–1232. Bibcode:2015PBioJ..13.1224D. doi:10.1111/pbi.12292. PMID 25417596.
  3. 1 2 Kumar, Naresh; Pruthi, Vikas (December 2014). "Potential applications of ferulic acid from natural sources". Biotechnology Reports. 4: 86–93. doi:10.1016/j.btre.2014.09.002. ISSN 2215-017X. PMC 5466124. Archived from the original on 2024-03-30.
  4. ↑ Hlasiwetz, H.; Barth, L (January 1866). "Mittheilungen aus dem chemischen Laboratorium in Innsbruck I)Ueber einige Harze [Zersetzungsproducte derselben durch schmelzendes Kali]". Justus Liebigs Annalen der Chemie. 138 (1): 61–76. doi:10.1002/jlac.18661380111. ISSN 0075-4617.
  5. ↑ Luthria, Devanand L.; Pastor-Corrales, Marcial A. (2006). "Phenolic acids content of fifteen dry edible bean (Phaseolus vulgaris L.) varieties". Journal of Food Composition and Analysis. 19 (2–3): 205–211. doi:10.1016/j.jfca.2005.09.003.
  6. ↑ Anson, Nuria Mateo; van den Berg, Robin; Bast, Aalt; Haenen, Guido R. M. M. (2009). "Bioavailability of ferulic acid is determined by its bioaccessibility". Journal of Cereal Science. 49 (2): 296–300. doi:10.1016/j.jcs.2008.12.001.
  7. ↑ Gelinas, Pierre; McKinnon, Carole M. (2006). "Effect of wheat variety, farming site, and bread-baking on total phenolics". International Journal of Food Science and Technology. 41 (3): 329–332. doi:10.1111/j.1365-2621.2005.01057.x.
  8. ↑ Buranov, Anvar U.; Mazza, G. (2009). "Extraction and purification of ferulic acid from flax shives, wheat and corn bran by alkaline hydrolysis and pressurised solvents". Food Chemistry. 115 (4): 1542–1548. doi:10.1016/j.foodchem.2009.01.059.
  9. ↑ Beejmohun, Vickram; Fliniaux, Ophélie (2007). "Microwave-assisted extraction of the main phenolic compounds in flaxseed". Phytochemical Analysis. 18 (4): 275–285. Bibcode:2007PChAn..18..275B. doi:10.1002/pca.973. PMID 17623361.
  10. ↑ Quinde-Axtell, Zory; Baik, Byung-Kee (2006). "Phenolic Compounds of Barley Grain and Their Implication in Food Product Discoloration". J. Agric. Food Chem. 54 (26): 9978–84. Bibcode:2006JAFC...54.9978Q. doi:10.1021/jf060974w. PMID 17177530.
  11. ↑ "Cooking sweet corn boosts its ability to fight cancer and heart disease by freeing healthful compounds, Cornell scientists find". Cornell News. Retrieved 2009-09-07.
  12. ↑ Orthoefer, F. T. (2005). "Chapter 10: Rice Bran Oil". In Shahidi, F. (ed.). Bailey's Industrial Oil and Fat Products. Vol. 2 (6th ed.). John Wiley & Sons, Inc. p. 465. ISBN 978-0-471-38552-3. Retrieved 2012-03-01.
  13. ↑ Strandås, C.; Kamal-Eldin, A.; Andersson, R.; Åman, P. (2008). "Phenolic glucosides in bread containing flaxseed". Food Chemistry. 110 (4): 997–999. doi:10.1016/j.foodchem.2008.02.088. PMID 26047292.
  14. ↑ Boskov Hansen, H.; Andreasen, M.; Nielsen, M.; Larsen, L.; Knudsen, Bach K.; Meyer, A.; Christensen, L.; Hansen, Å. (2014). "Changes in dietary fibre, phenolic acids and activity of endogenous enzymes during rye bread-making". European Food Research and Technology. 214 (1): 33–42. doi:10.1007/s00217-001-0417-6. ISSN 1438-2377. S2CID 85239461.
  15. ↑ Zhao, Zhaohui; Moghadasian, Mohammed H. (August 2008). "Chemistry, natural sources, dietary intake and pharmacokinetic properties of ferulic acid: A review". Food Chemistry. 109 (4): 691–702. doi:10.1016/j.foodchem.2008.02.039. PMID 26049981.
  16. ↑ Kumar, Naresh; Pruthi, Vikas (December 2014). "Potential applications of ferulic acid from natural sources". Biotechnology Reports. 4: 86–93. doi:10.1016/j.btre.2014.09.002. PMC 5466124. PMID 28626667.
  17. ↑ Shahadi, Fereidoon; Naczk, Marian (2004). Phenolics in Food and Nutraceuticals. Florida: CRC Press. p. 4. ISBN 978-1-58716-138-4.
  18. ↑ Kang, Sun-Young; Choi, Oksik; Lee, Jae Kyung; Hwang, Bang Yeon; Uhm, Tai-Boong; Hong, Young-Soo (December 2012). "Artificial biosynthesis of phenylpropanoic acids in a tyrosine overproducing Escherichia coli strain". Microbial Cell Factories. 11 (1): 153. doi:10.1186/1475-2859-11-153. PMC 3554431. PMID 23206756.
  19. ↑ Iiyama, K.; Lam, T. B.-T.; Stone, B. A. (1994). "Covalent Cross-Links in the Cell Wall". Plant Physiology. 104 (2): 315–320. doi:10.1104/pp.104.2.315. ISSN 0032-0889. PMC 159201. PMID 12232082.
  20. ↑ Bagchi, Debasis; Moriyama, Hiroyoshi; Swaroop, Anand (2016). Green Coffee Bean Extract in Human Health. CRC Press. p. 92. ISBN 9781315353982. Retrieved 23 September 2017.
  21. ↑ Huang, Z.; Dostal, L.; Rosazza, J. P. (1993). "Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens ". Applied and Environmental Microbiology. 59 (7): 2244–2250. Bibcode:1993ApEnM..59.2244H. doi:10.1128/AEM.59.7.2244-2250.1993. PMC 182264. PMID 8395165.
  22. ↑ Huang, Z.; Dostal, L.; Rosazza, J. P. (1994). "Purification and characterization of a ferulic acid decarboxylase from Pseudomonas fluorescens". Journal of Bacteriology. 176 (19): 5912–5918. doi:10.1128/jb.176.19.5912-5918.1994. PMC 196807. PMID 7928951.
  23. ↑ Kalogeraki, Virginia S.; Zhu, Jun; Eberhard, Anatol; Madsen, Eugene L.; Winans, Stephen C. (November 1999). "The phenolic vir gene inducer ferulic acid is O-demethylated by the VirH2 protein of an Agrobacterium tumefaciens Ti plasmid". Molecular Microbiology. 34 (3): 512–522. doi:10.1046/j.1365-2958.1999.01617.x. PMID 10564493. S2CID 28658847.
  24. ↑ Cavalcanti, Gabriela R.; Duarte, Fernanda I.C.; Converti, Attilio; de Lima, Ádley A.N. (May 2021). "Ferulic Acid Activity in Topical Formulations: Technological and Scientific Prospecting". Current Pharmaceutical Design. 27 (19): 2289–2298. doi:10.2174/1381612826666201020163331. hdl:11567/1050300. ISSN 1381-6128.