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Ferulic acid

From Wikipedia, the free encyclopedia
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 InfoCard100.007.892Edit 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 mass194.186 g·mol−1
AppearanceCrystalline powder
Melting point168 to 172 °C (334 to 342 °F; 441 to 445 K)
0.78 g/L[1]
Acidity (pKa)4.61[1]
Hazards
NFPA 704 (fire diamond)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Ferulic acid is ahydroxycinnamic acidderivative and aphenolic compound. It is an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genusFerula, referring to the giant fennel (Ferula communis). Classified as aphenolicphytochemical, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plantcell walls, covalently bonded tohemicellulose such asarabinoxylans.[2] Salts and esters derived from ferulic acid are calledferulates.

Occurrence in nature

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Ferulic acid is ubiquitous in the plant kingdom, including a number of vegetable sources. It occurs in particularly high concentrations inpopcorn andbamboo shoots.[3][4] It is a major metabolite ofchlorogenic acids in humans along withcaffeic andisoferulic acid, and is absorbed in thesmall intestine, whereas other metabolites such asdihydroferulic acid,feruloylglycine and dihydroferulic acid sulfate are produced from chlorogenic acid in thelarge intestine by the action ofgut flora.[5]

In cereals, ferulic acid is localized in thebran – the hard outer layer of grain. Inwheat, phenolic compounds are mainly found in the form of insoluble bound ferulic acid and may be relevant to resistance to wheat fungal diseases.[6] The highest known concentration of ferulic acidglucoside has been found inflaxseed (4.1±0.2 g/kg).[7] It is also found inbarley grain.[8]

Asterideudicot plants can also produce ferulic acid. The tea brewed from the leaves ofyacón (Smallanthus sonchifolius), a plant traditionally grown in the northern and centralAndes, contains quantities of ferulic acid. Inlegumes, the white bean varietynavy bean is the richest source of ferulic acid among the common bean (Phaseolus vulgaris) varieties.[9] It is also found inhorse grams (Macrotyloma uniflorum).[citation needed]

Although there are many sources of ferulic acid in nature, itsbioavailability 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 tocell wallpolysaccharides, allowing it to be released and absorbed in the small intestine.[10]

In processed foods

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Cookedsweetcorn releases increased levels of ferulic acid.[11] Asplant sterolesters, this compound is naturally found inrice bran oil, a popular cooking oil in several Asian countries.[12]

Ferulic acidglucoside can be found in commercialbreads containingflaxseed.[13]Rye bread containsferulic acid dehydrodimers.[14]

Metabolism

[edit]
In plants, ferulic acid (right) is derived fromphenylalanine (not shown), which is converted to4-hydroxycinnamic acid (left) and thencaffeic acid (center).

Biosynthesis

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Ferulic acid is biosynthesized in plants fromcaffeic acid by the action of the enzymecaffeateO-methyltransferase.[15][2]

In a proposed ferulic acid biosynthetic pathway forEscherichia coli,L-tyrosine is converted to4-coumaric acid bytyrosine ammonia lyase, which is converted to caffeic acid by Sam5, which is then converted to ferulic acid by caffeic acid methyltransferase.[16]

Ferulic acid, together withdihydroferulic acid, is a component oflignocellulose, serving to crosslink the lignin and polysaccharides, thereby conferring rigidity to the cell walls.[17]

It is an intermediate in the synthesis ofmonolignols, the monomers oflignin, and is also used for the synthesis oflignans.

Biodegradation

[edit]

Ferulic acid is converted by certain strains of yeast, notably strains used in brewing ofwheat beers, such asSaccharomyces delbrueckii (Torulaspora delbrueckii), to4-vinyl guaiacol (2-methoxy-4-vinylphenol) which gives beers such asWeissbier and Wit their distinctive clove-like flavour.Saccharomyces cerevisiae (dry baker's yeast) andPseudomonas fluorescens are also able to converttrans-ferulic acid into 2-methoxy-4-vinylphenol.[18] InP. fluorescens, aferulic acid decarboxylase has been isolated.[19]

Ecology

[edit]

Ferulic acid is one of the compounds that initiate thevir (virulence) region ofAgrobacterium tumefaciens, inducing it to infect plant cells.[20]

Extraction

[edit]

It can be extracted from wheat bran and maize bran using concentrated alkali.[21]

UV–visible spectrum of ferulic acid, withλmax at 321 nm and a shoulder at 278 nm

See also

[edit]

References

[edit]
  1. ^abMota, 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. ^abDe 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. ^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.
  4. ^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.
  5. ^Bagchi, Debasis; Moriyama, Hiroyoshi; Swaroop, Anand (2016).Green Coffee Bean Extract in Human Health. CRC Press. p. 92.ISBN 9781315353982. Retrieved23 September 2017.
  6. ^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.
  7. ^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.
  8. ^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.
  9. ^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.
  10. ^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.
  11. ^"Cooking sweet corn boosts its ability to fight cancer and heart disease by freeing healthful compounds, Cornell scientists find". Cornell News. Retrieved2009-09-07.
  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. Retrieved2012-03-01.
  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. ^Shahadi, Fereidoon; Naczk, Marian (2004).Phenolics in Food and Nutraceuticals. Florida: CRC Press. p. 4.ISBN 978-1-58716-138-4.
  16. ^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.
  17. ^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.
  18. ^Huang, Z.; Dostal, L.; Rosazza, J. P. (1993)."Microbial transformations of ferulic acid bySaccharomyces cerevisiae andPseudomonas 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.
  19. ^Huang, Z.; Dostal, L.; Rosazza, J. P. (1994)."Purification and characterization of a ferulic acid decarboxylase fromPseudomonas fluorescens".Journal of Bacteriology.176 (19):5912–5918.doi:10.1128/jb.176.19.5912-5918.1994.PMC 196807.PMID 7928951.
  20. ^Kalogeraki, Virginia S.; Zhu, Jun; Eberhard, Anatol; Madsen, Eugene L.; Winans, Stephen C. (November 1999)."The phenolicvir gene inducer ferulic acid isO-demethylated by the VirH2 protein of anAgrobacterium tumefaciens Ti plasmid".Molecular Microbiology.34 (3):512–522.doi:10.1046/j.1365-2958.1999.01617.x.PMID 10564493.S2CID 28658847.
  21. ^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.
Aglycones
Precursor
Monohydroxycinnamic acids
(Coumaric acids)
Dihydroxycinnamic acids
Trihydroxycinnamic acids
O-methylated forms
others
Esters
glycoside-likes
Esters of
caffeic acid
with cyclitols
esters of
quinic acid
esters of
shikimic acid
Glycosides
Tartaric acid esters
Other esters
with caffeic acid
Caffeoyl phenylethanoid
glycoside (CPG)
Oligomeric forms
Dimers
Trimers
Tetramers
Conjugates with
coenzyme A (CoA)
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