Ferulic acid
Ferulic acid is a hydroxycinnamic acid
Hydroxycinnamic acid
Hydroxycinnamic acids are a class of polyphenols having a C6-C3 skeleton. These compounds are hydroxy derivatives of cinnamic acid.In the category of phytochemicals that can be found in food, there are :* Alpha-cyano-4-hydroxycinnamic acid...

, a type of organic compound. It is an abundant phenolic phytochemical found in plant cell wall
Cell wall
The cell wall is the tough, usually flexible but sometimes fairly rigid layer that surrounds some types of cells. It is located outside the cell membrane and provides these cells with structural support and protection, and also acts as a filtering mechanism. A major function of the cell wall is to...

 components such as arabinoxylan
Arabinoxylan is a hemicellulose found in both the primary and secondary cell walls of plants, including woods and cereal grains, consisting of copolymers of two pentose sugars – arabinose and xylose.-Structure:...

s as covalent side chains. It is related to trans-cinnamic acid
Cinnamic acid
Cinnamic acid is a white crystalline organic acid, which is slightly soluble in water.It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter and is the best indication of its environmental history and post-extraction conditions...

. As a component of lignin, ferulic acid is a precursor in the manufacture of other aromatic compounds. The etymology is from Ferula
Ferula is a genus of about 170 species of flowering plants in the family Apiaceae, native to the Mediterranean region east to central Asia, mostly growing in arid climates. They are herbaceous perennial plants growing to 1–4 m tall, with stout, hollow, somewhat succulent stems...

, referring to the giant fennel (Ferula communis).

Occurrence in nature

Ferulic acid is found in the seeds of coffee
Coffee is a brewed beverage with a dark,init brooo acidic flavor prepared from the roasted seeds of the coffee plant, colloquially called coffee beans. The beans are found in coffee cherries, which grow on trees cultivated in over 70 countries, primarily in equatorial Latin America, Southeast Asia,...

, apple
The apple is the pomaceous fruit of the apple tree, species Malus domestica in the rose family . It is one of the most widely cultivated tree fruits, and the most widely known of the many members of genus Malus that are used by humans. Apple grow on small, deciduous trees that blossom in the spring...

, artichoke
-Plants:* Globe artichoke, a partially edible perennial thistle originating in southern Europe around the Mediterranean* Jerusalem artichoke, a species of sunflower with an edible tuber...

, peanut
The peanut, or groundnut , is a species in the legume or "bean" family , so it is not a nut. The peanut was probably first cultivated in the valleys of Peru. It is an annual herbaceous plant growing tall...

, and orange
Orange (fruit)
An orange—specifically, the sweet orange—is the citrus Citrus × sinensis and its fruit. It is the most commonly grown tree fruit in the world....

, as well as in both seeds and cell wall
Cell wall
The cell wall is the tough, usually flexible but sometimes fairly rigid layer that surrounds some types of cells. It is located outside the cell membrane and provides these cells with structural support and protection, and also acts as a filtering mechanism. A major function of the cell wall is to...

s of commelinid
In plant taxonomy, commelinids is a name used by the APG III system for a clade within the monocots, which in its turn is a clade within the angiosperms. The commelinids are the only clade that the APG has informally named within the monocots...

 plants (such as rice
Rice is the seed of the monocot plants Oryza sativa or Oryza glaberrima . As a cereal grain, it is the most important staple food for a large part of the world's human population, especially in East Asia, Southeast Asia, South Asia, the Middle East, and the West Indies...

, wheat
Wheat is a cereal grain, originally from the Levant region of the Near East, but now cultivated worldwide. In 2007 world production of wheat was 607 million tons, making it the third most-produced cereal after maize and rice...

, oats
OATS - Open Source Assistive Technology Software - is a source code repository or "forge" for assistive technology software. It was launched in 2006 with the goal to provide a one-stop “shop” for end users, clinicians and open-source developers to promote and develop open source assistive...

, and pineapple
Pineapple is the common name for a tropical plant and its edible fruit, which is actually a multiple fruit consisting of coalesced berries. It was given the name pineapple due to its resemblance to a pine cone. The pineapple is by far the most economically important plant in the Bromeliaceae...

). It can be extracted from wheat bran and maize bran using concentrated alkali.

Açaí oil
Acai oil
Açaí oil is obtained from the fruit of Euterpe oleracea , which grows in the Amazon Rainforest. The oil is rich in phenolic compounds similar in profile to the pulp itself, such as vanillic acid, syringic acid, p-hydroxybenzoic acid, protocatechuic acid and ferulic acid as well as -catechin and...

, obtained from the fruit of the açaí palm (Euterpe oleracea), is rich in ferulic acid (101 +/- 5.9 mg/kg).


Biosynthesis is an enzyme-catalyzed process in cells of living organisms by which substrates are converted to more complex products. The biosynthesis process often consists of several enzymatic steps in which the product of one step is used as substrate in the following step...

 of ferulic acid is by the action of the enzyme O-methyl transferase on caffeic acid
Caffeic acid
Caffeic acid is a hydroxycinnamic acid, a naturally occurring organic compound. This yellow solid consists of both phenolic and acrylic functional groups...

.It is biosynthesised from caffeic acid
Caffeic acid
Caffeic acid is a hydroxycinnamic acid, a naturally occurring organic compound. This yellow solid consists of both phenolic and acrylic functional groups...


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 monolignol
Monolignols are phytochemicals acting as source materials for biosynthesis of both lignans and lignin. The starting material for production of monolignols is the amino acid phenylalanine. The first reactions in the biosynthesis are shared with the phenylpropanoid pathway, and monolignols are...

s, i.e., the monomers of lignin
Lignin or lignen is a complex chemical compound most commonly derived from wood, and an integral part of the secondary cell walls of plants and some algae. The term was introduced in 1819 by de Candolle and is derived from the Latin word lignum, meaning wood...

, and is also used for the synthesis of lignans.

Ferulic acid is converted by certain strains of yeast (notably strains of yeast used in brewing of wheat beers, such as Saccharomyces delbrueckii
Torulaspora delbrueckii
Torulaspora delbrueckii is a yeast species which is also known as Saccharomyces delbrueckii or Saccharomyces rosei .The genetic analyses have revealed that the various strains treated as T...

) to 4-vinyl guaiacol which gives beers such as Weissbier
Weissbier , also known as Weizenbier , is a Bavarian specialty beer in which a significant proportion of malted barley is replaced with malted wheat: a wheat beer. By German law, Weissbiers brewed in Germany must be top-fermented...

 and Wit their distinctive "clove" flavour.

Bio-medical considerations

Ferulic acid, like many phenol
Natural phenol
Natural phenols, bioavailable phenols, plant phenolics, low molecular weight phenols or phenoloids are a class of natural products. They are small molecules containing one or more phenolic group. These molecules are smaller in size than polyphenols, containing less than 12 phenolic groups...

s, is an antioxidant
An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...

 in vitro
In vitro
In vitro refers to studies in experimental biology that are conducted using components of an organism that have been isolated from their usual biological context in order to permit a more detailed or more convenient analysis than can be done with whole organisms. Colloquially, these experiments...

 in the sense that it is reactive toward free radicals such as reactive oxygen species
Reactive oxygen species
Reactive oxygen species are chemically reactive molecules containing oxygen. Examples include oxygen ions and peroxides. Reactive oxygen species are highly reactive due to the presence of unpaired valence shell electrons....

 (ROS). ROS and free radicals are implicated in DNA damage, cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...

, accelerated cell aging
Senescence or biological aging is the change in the biology of an organism as it ages after its maturity. Such changes range from those affecting its cells and their function to those affecting the whole organism...

. Animal studies and in vitro studies suggest that ferulic acid may have direct antitumor activity against breast cancer
Breast cancer
Breast cancer is cancer originating from breast tissue, most commonly from the inner lining of milk ducts or the lobules that supply the ducts with milk. Cancers originating from ducts are known as ductal carcinomas; those originating from lobules are known as lobular carcinomas...

and liver cancer
Hepatocellular carcinoma
Hepatocellular carcinoma is the most common type of liver cancer. Most cases of HCC are secondary to either a viral hepatitide infection or cirrhosis .Compared to other cancers, HCC is quite a rare tumor in the United States...

. Ferulic acid may have pro-apoptotic
Apoptosis is the process of programmed cell death that may occur in multicellular organisms. Biochemical events lead to characteristic cell changes and death. These changes include blebbing, cell shrinkage, nuclear fragmentation, chromatin condensation, and chromosomal DNA fragmentation...

 effects in cancer cells, thereby leading to their destruction. Ferulic acid may be effective at preventing cancer induced by exposure to the carcinogenic compounds benzopyrene
Benzo[a]pyrene, C20H12, is a five-ring polycyclic aromatic hydrocarbon whose metabolites are mutagenic and highly carcinogenic. Benzo[a]pyrene is listed as a Group 1 carcinogen by the IARC. It belongs to a class of polycyclic aromatic compounds known as benzopyrenes, which consist of a benzene...

and 4-nitroquinoline 1-oxide
4-Nitroquinoline 1-oxide
4-Nitroquinoline 1-oxide is a quinoline derivative and a tumorigenic compound used in the assessment of the efficacy of diets, drugs, and procedures in the prevention and treatment of cancer in animal models. It induces DNA lesions usually corrected by nucleotide excision repair.-References:* in...

. Note that these are not randomized controlled trial
Randomized controlled trial
A randomized controlled trial is a type of scientific experiment - a form of clinical trial - most commonly used in testing the safety and efficacy or effectiveness of healthcare services or health technologies A randomized controlled trial (RCT) is a type of scientific experiment - a form of...

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
Ascorbic acid
Ascorbic acid is a naturally occurring organic compound with antioxidant properties. It is a white solid, but impure samples can appear yellowish. It dissolves well in water to give mildly acidic solutions. Ascorbic acid is one form of vitamin C. The name is derived from a- and scorbutus , the...

 and vitamin E
Vitamin E
Vitamin E is used to refer to a group of fat-soluble compounds that include both tocopherols and tocotrienols. There are many different forms of vitamin E, of which γ-tocopherol is the most common in the North American diet. γ-Tocopherol can be found in corn oil, soybean oil, margarine and dressings...

, ferulic acid may reduce oxidative stress
Oxidative stress
Oxidative stress represents an imbalance between the production and manifestation of reactive oxygen species and a biological system's ability to readily detoxify the reactive intermediates or to repair the resulting damage...

 and formation of thymine dimers in skin
-Dermis:The dermis is the layer of skin beneath the epidermis that consists of connective tissue and cushions the body from stress and strain. The dermis is tightly connected to the epidermis by a basement membrane. It also harbors many Mechanoreceptors that provide the sense of touch and heat...


As a precursor to vanillin

Ferulic acid, being highly abundant, may be useful as a precursor in the manufacturing of vanillin
Vanillin is a phenolic aldehyde, an organic compound with the molecular formula C8H8O3. Its functional groups include aldehyde, ether, and phenol. It is the primary component of the extract of the vanilla bean. It is also found in Leptotes bicolor, roasted coffee and the Chinese red pine...

, a synthetic flavoring agent often used in place of natural vanilla
Vanilla is a flavoring derived from orchids of the genus Vanilla, primarily from the Mexican species, Flat-leaved Vanilla . The word vanilla derives from the Spanish word "", little pod...

 extract. However, biotechnological processes may be the most efficient method to use ferulic acid as a precursor, and as such, research is still ongoing.

Mass spectrometry

It is used as a matrix for protein
Proteins are biochemical compounds consisting of one or more polypeptides typically folded into a globular or fibrous form, facilitating a biological function. A polypeptide is a single linear polymer chain of amino acids bonded together by peptide bonds between the carboxyl and amino groups of...

s in MALDI
Matrix-assisted laser desorption/ionization
Matrix-assisted laser desorption/ionization is a soft ionization technique used in mass spectrometry, allowing the analysis of biomolecules and large organic molecules , which tend to be fragile and fragment when ionized by more conventional ionization methods...

 mass spectrometry
Mass spectrometry
Mass spectrometry is an analytical technique that measures the mass-to-charge ratio of charged particles.It is used for determining masses of particles, for determining the elemental composition of a sample or molecule, and for elucidating the chemical structures of molecules, such as peptides and...


Bitterness masker

Kraft Foods
Kraft Foods
Kraft Foods Inc. is an American confectionery, food and beverage conglomerate. It markets many brands in more than 170 countries. 12 of its brands annually earn more than $1 billion worldwide: Cadbury, Jacobs, Kraft, LU, Maxwell House, Milka, Nabisco, Oscar Mayer, Philadelphia, Trident, Tang...

 has patented the use of sodium ferulate to mask the bitter aftertaste
Aftertaste is the taste intensity of a food or beverage that is perceived immediately after that food or beverage is removed from the mouth. The aftertastes of different foods and beverages can vary by intensity and over time, but the unifying feature of aftertaste is that it is perceived after a...

 of the artificial sweetener acesulfame potassium
Acesulfame potassium
Acesulfame potassium is a calorie-free artificial sweetener, also known as Acesulfame K or Ace K , and marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number E950...


See also

  • Caffeic acid
    Caffeic acid
    Caffeic acid is a hydroxycinnamic acid, a naturally occurring organic compound. This yellow solid consists of both phenolic and acrylic functional groups...

  • Coumaric acid
    Coumaric acid
    Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group...

  • Diferulic acids
    Diferulic acids
    Diferulic acids are organic compounds that have the general chemical formula C20H18O8, they are formed by dimerisation of ferulic acid. Just as ferulic acid is not the proper IUPAC name, the diferulic acids also tend to have trivial names that are more commonly used than the correct IUPAC name...

  • Sodium ferulate
    Sodium ferulate
    Sodium ferulate , the sodium salt of ferulic acid, is a drug used in traditional Chinese medicine for treatment of cardiovascular and cerebrovascular diseases and to prevent thrombosis. It is found in the root of Angelica sinensis. It is considered safe and effective...

    , a ferulic acid salt
The source of this article is wikipedia, the free encyclopedia.  The text of this article is licensed under the GFDL.