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Ferulic acid

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This is an old revision of this page, as edited by 92.231.94.167 (talk) at 09:41, 5 November 2012 (Did anyone ever read the title of the source? It says "phytochemical ENRICHED oil". That's certainly not ordinary Acai oil. Smelled like marketing anyway.). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Ferulic acid
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.013.173 Edit this at Wikidata
  • 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 194.18 g/mol
Appearance Crystalline Powder
Melting point 168–172 °C
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).
checkY verify (what is checkY☒N ?)

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

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

It is one of the phenolic compounds found in the invasive plant species carpobrotus edulis and contributes to the antibacterial[1] and antioxidant[2] properties of the plant.

In food

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, the Chinese water chestnut (Eleocharis dulcis) and pineapple).

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.[3] The highest known concentration of ferulic acid glucoside has been found in flax seed (4.1 +/- 0.2 g/kg).[4]

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.[5] In legumes, the white bean variety navy bean is the richest source of ferulic acid among the common bean (Phaseolus vulgaris) varieties.[6] It is also found in horse grams (Macrotyloma uniflorum).[7]

In processed foods

Cooked sweet corn releases increased levels of ferulic acid.[8] The compound is also found in rice bran oil, a popular cooking oil in several Asian countries.[9]

Ferulic acid glucoside can be found in commercial breads containing flaxseed.[10] Rye bread contains ferulic acid dehydrodimers.[11]

Metabolism

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

Biosynthesis

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.[12]

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

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.[13] In P. fluorescens, a ferulic acid decarboxylase has been isolated.[14]

Ecology

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

Extraction

It can be extracted from wheat bran and maize bran using concentrated alkali.[15]

Bio-medical considerations

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.[16]

Other applications

As a precursor to vanillin

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

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

Bitterness masker

Kraft Foods has patented the use of sodium ferulate to mask the bitter aftertaste of the artificial sweetener acesulfame potassium.[17]

See also

References

  1. ^ Purification and identification of active antibacterial components in Carpobrotusedulis L. Elmarie van der Watt and Johan C Pretorius, Journal of Ethnopharmacology, Volume 76, Issue 1, June 2001, Pages 87–91, doi:10.1016/S0378-8741(01)00197-0
  2. ^ Antioxidant and Antibacterial Properties of Mesembryanthemum crystallinum and Carpobrotus edulis Extracts. Bouftira Ibtissem, Chedly Abdelly and Souad Sfar, Advances in Chemical Engineering and Science, 2012, Vol. 2 No. 3, pages 359-365, doi:10.4236/aces.2012.23042
  3. ^ 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. doi:10.1111/j.1365-2621.2005.01057.x.
  4. ^ Beejmohun, Vickram; Fliniaux, Ophélie (2007). "Microwave-assisted extraction of the main phenolic compounds in flaxseed". Phytochemical Analysis. 18 (4): 275–285. doi:10.1002/pca.973.
  5. ^ Valentão, P.; Fernandes, E.; Carvalho, F.; Andrade, P. B.; Seabra, R. M.; Bastos, M. L. (2001). "Antioxidant Activity ofCentaurium erythraeaInfusion Evidenced by Its Superoxide Radical Scavenging and Xanthine Oxidase Inhibitory Activity". Journal of Agricultural and Food Chemistry. 49 (7): 3476–9. doi:10.1021/jf001145s. PMID 11453794.
  6. ^ Devanand L. Luthria, Marcial A. Pastor-Corrales. Phenolic acids content of fifteen dry edible bean (Phaseolus vulgaris L.) varieties. Journal of Food Composition and Analysis, 2006, 19, pages 205–211
  7. ^ Kawsar, S.M.A.; Huq, E.; Nahar, N.; Ozeki, Y. (2008). "Identification and Quantification of Phenolic Acids in Macrotyloma uniflorum by Reversed Phase-HPLC". American Journal of Plant Physiology. 3 (4): 165. doi:10.3923/ajpp.2008.165.172.
  8. ^ "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.
  9. ^ Orthoefer, F. T. (2005). "Chapter 10: Rice Bran Oil". In Shahidi, F. (ed.). Bailey's Industrial Oil and Fat Products. Vol. 2 (6 ed.). John Wiley & Sons, Inc. p. 465. ISBN 978-0-471-38552-3. Retrieved 2012-03-01.
  10. ^ Strandås, C.; Kamal-Eldin, A.; Andersson, R.; Åman, P. (2008). "Phenolic glucosides in bread containing flaxseed". Food Chemistry. 110 (4): 997. doi:10.1016/j.foodchem.2008.02.088.
  11. ^ m., Andreasen; m., Nielsen; Knudsen, Bach; a., Meyer; l., Christensen; �., Hansen; Hansen, H. Boskov; l., Larsen (2002). "Changes in dietary fibre, phenolic acids and activity of endogenous enzymes during rye bread-making". European Food Research and Technology. 214: 33. doi:10.1007/s00217-001-0417-6. {{cite journal}}: |last6= has numeric name (help); replacement character in |last6= at position 1 (help)
  12. ^ . doi:10.1104/pp.104.2.315. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  13. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 8395165, please use {{cite journal}} with |pmid=8395165 instead.
  14. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 7928951, please use {{cite journal}} with |pmid=7928951 instead.
  15. ^ Buranov, Anvar U. (15 August 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. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  16. ^ Experimental Dermatology, August 2005, pages 601-608; Bioscience, Biotechnology, and Biochemistry, December 2005, pages 2368-2373; International Journal of Dermatology, August 2004, pages 604-607; Journal of Drugs in Dermatology, July–August 2004, pages 377-381; Facial and Plastic Surgery, February 2004, pages 3-9; Dermatologic Surgery, March 2004, pages 385-388; Journal of Bioscience and Bioengineering, March 2005, pages 272-276; Journal of Biological Chemistry, November 7, 2003, pages 44320-44325; Journal of Agriculture and Food Chemistry, February 2003, pages 1201-1207; International Journal of Cosmetic Science, August 2000, pages 291-303; and Anti-Cancer Research, September–October 1999, pages 3769-3774.
  17. ^ United States Patent 5,336,513

Notes

  1. a Shahadi, Fereidoon (2004). Phenolics in food and nutraceuticals. Florida, USA: CRC Press LLC. p. 4. ISBN 1-58716-138-9. {{cite book}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  2. a Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 14979919, please use {{cite journal}} with |pmid=14979919 instead.
  3. a b Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 16276977, please use {{cite journal}} with |pmid=16276977 instead.
  4. a Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 6317220, please use {{cite journal}} with |pmid=6317220 instead.
  5. a Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 10625957, please use {{cite journal}} with |pmid=10625957 instead.
  6. a Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 16185284, please use {{cite journal}} with |pmid=16185284 instead.
  7. a Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 15493526, please use {{cite journal}} with |pmid=15493526 instead.
  8. a Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 11548997, please use {{cite journal}} with |pmid=11548997 instead.
  9. a Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 2520223, please use {{cite journal}} with |pmid=2520223 instead.
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)