Ferulic acid
2630110
213680040
2008-05-20T11:26:12Z
130.237.78.239
/* Occurrence in nature */
{{Chembox new
| ImageFile = Ferulic acid acsv.svg
| ImageSize = 250px
| IUPACName = (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acid
| OtherNames = 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
| Section1 = {{Chembox Identifiers
| CASNo=537-98-4
| PubChem=445858
| SMILES=COC1=C(C=CC(=C1)C=CC(=O)O)O
}}
| Section2 = {{Chembox Properties
| Formula=C<sub>10</sub>H<sub>10</sub>O<sub>4</sub>
| MolarMass=194.184
| Appearance=
| Density=
| MeltingPt= 168-172 °C
| BoilingPt=
| Solubility=
}}
| Section3 = {{Chembox Hazards
| MainHazards=
| FlashPt=
| Autoignition=
}}
}}
'''Ferulic acid''' is an [[organic compound]] that is an abundant [[phenolic]] [[phytochemical]] found in plant [[cell wall]]s. It is a derivative of trans-[[cinnamic acid]]. As a component of lignin, ferulic acid is a [[wiktionary:Precursor|precursor]] in the manufacture of other [[aromatic]] compounds.
Etymology : from Ferula, giant fennel.
==Occurrence in nature==
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.<ref>Iiyama, K.; Lam, T B.-L.; Stone, B. A. "Covalent Cross-Links in the Cell Wall" Plant Physiology, 1994 volume 104, pp. 315-320.</ref> It is found in seeds of plants such as in [[rice]], [[wheat]], and [[oats]], as well as in [[coffee]], [[apple]], [[artichoke]], [[peanut]], [[orange (fruit)|orange]] and [[pineapple]]. It can be extracted from wheat bran and maize bran using concentrated alkali. [[Biosynthesis]] of ferulic acid is by the action of the enzyme O-methyl transferase on [[caffeic acid]] {{ref_label|1|1|a}}.
It is an intermediate in the synthesis of monolignols, i.e., the monomers of [[lignin]], and is also used for the synthesis of [[lignans]].
==Bio-medical considerations==
Ferulic acid, like many [[phenol]]s, is an [[antioxidant]] in the sense that it is reactive toward [[free radical]]s such as [[reactive oxygen species]] (ROS). ROS and free radicals are implicated in [[DNA repair#DNA damage|DNA damage]], [[cancer]], accelerated cell [[senescence|aging]]. Animal studies and [[in vitro]] studies suggest that ferulic acid may have direct antitumor activity against [[breast cancer]] {{ref_label|2|2|a}} and [[Hepatocellular carcinoma|liver cancer]] {{ref_label|3|3|a}}. Ferulic acid may have pro-[[apoptosis|apoptotic]] effects in cancer cells, thereby leading to their destruction {{ref_label|3|3|b}}. Ferulic acid may be effective at preventing cancer induced by exposure to the carcinogenic compounds [[benzopyrene]] {{ref_label|4|4|a}} and [[4-nitroquinoline 1-oxide]] {{ref_label|5|5|a}}. Note that these are not [[randomized controlled trial]]s 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 dimer]]s in [[skin]] {{ref_label|6|6|a}}.
==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 {{ref_label|7|7|a}}. However, biotechnological processes may be the most efficient method to use ferulic acid as a precursor {{ref_label|8|8|a}}, and as such, research is still ongoing.
===Mass spectrometry===
It is used as a matrix for [[protein]]s in [[Matrix-assisted laser desorption/ionization|MALDI]] [[mass spectroscopy]] analyses. {{ref_label|9|9|a}}
==See also==
* [[Caffeic acid]]
* [[Coumaric acid]]
* [[Diferulic acids]]
* [[Sodium ferulate]], a ferulic acid salt
==References==
{{reflist}}
# {{note_label|1|1|a}} {{cite book |author= Shahadi, Fereidoon|coauthors= Naczk, Marian|title= Phenolics in food and nutraceuticals| origyear= 2004|publisher= CRC Press LLC|location= Florida, USA|isbn= 1-58716-138-9|pages= pp. 4|}}
# {{note_label|2|2|a}} [[Image:Free text.png]] Antiproliferative and apoptotic effects of selective phenolic acids on T47D human breast cancer cells: potential mechanisms of action. ''Breast Cancer Res. 2004; 6(2: R63-74. Epub 2003 Dec 15; {{PMID|14979919}}'' {{PMID_free|14979919}}
# {{note_label|3|3|a}} {{note_label|2|2|b}} Role of NADPH oxidase-mediated generation of reactive oxygen species in the mechanism of apoptosis induced by phenolic acids in HepG2 human hepatoma cells. ''Arch Pharm Res. 2005 Oct; 28(10): 1183-9; {{PMID|16276977}}''
# {{note_label|4|4|a}} Protective effects of ellagic acid and other plant phenols on benzo[a]pyrene-induced neoplasia in mice. ''Carcinogenesis. 1983 Dec; 4(12): 1651-3; {{PMID|6317220}}''
# {{note_label|5|5|a}} Chemopreventive effects of ferulic acid on oral and rice germ on large bowel carcinogenesis. ''Anticancer Res. 1999 Sep-Oct; 19(5A): 3775-8; {{PMID|10625957}}''
# {{note_label|6|6|a}} Ferulic acid stabilizes a solution of vitamins C and E and doubles its photoprotection of skin. ''J Invest Dermatol. 2005 Oct; 125(4): 826-32; {{PMID|16185284}}''
# {{note_label|7|7|a}} Ferulic acid: an antioxidant found naturally in plant cell walls and feruloyl esterases involved in its release and their applications. ''Crit Rev Biotechnol. 2004; 24(2-3): 59-83; {{PMID|15493526}}''
# {{note_label|8|8|a}} Biotechnological production of vanillin. ''Appl Microbiol Biotechnol. 2001 Aug; 56(3-4): 296-314; {{PMID|11548997}}''
#{{note_label|9|9|a}} Beavis, R. C.; Chait, B. T., Cinnamic Acid Derivatives as Matrices for Ultraviolet Laser Desorption Mass Spectrometry of Proteins. ''Rapid Commun. Mass Spectrom.'' '''1989''', ''3'', 432-435; {{doi|10.1002/rcm.1290031207}}
[[Category:Antioxidants]]
[[Category:Phenols]]
[[Category:Carboxylic acids]]
[[Category:Phenylpropanoids]]
[[bg:Ферулова киселина]]
[[de:Ferulasäure]]
[[ja:フェルラ酸]]
[[pl:Kwas ferulowy]]
[[fi:Ferulahappo]]