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Ferulic acid information


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
CAS Number
  • 537-98-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17620 checkY
ChEMBL
  • ChEMBL32749 checkY
ChemSpider
  • 393368 checkY
DrugBank
  • DB07767 checkY
ECHA InfoCard 100.013.173 Edit this at Wikidata
PubChem CID
  • 445858
UNII
  • AVM951ZWST checkY
CompTox Dashboard (EPA)
  • DTXSID70892035 DTXSID5040673, DTXSID70892035 Edit this at Wikidata
InChI
  • 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
SMILES
  • COc1cc(ccc1O)/C=C/C(=O)O
Properties
Chemical formula
C10H10O4
Molar mass 194.18 g/mol
Appearance Crystalline powder
Melting point 168 to 172 °C (334 to 342 °F; 441 to 445 K)
Solubility in water
0.78 g/L[1]
Acidity (pKa) 4.61[1]
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).
Infobox references

Ferulic acid is a hydroxycinnamic acid; 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.[2] Salts and esters derived from ferulic acid are called ferulates.

  1. ^ a b Mota, Fátima L.; Queimada, António J.; Pinho, Simão P.; Macedo, Eugénia A. (August 2008). "Aqueous Solubility of Some Natural Phenolic Compounds". Industrial & Engineering Chemistry Research. 47 (15): 5182–5189. doi:10.1021/ie071452o. hdl:10198/1506.
  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. doi:10.1111/pbi.12292. PMID 25417596.

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Ferulic acid

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Ferulic acid is a hydroxycinnamic acid; it is an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring...

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Ferulic acid decarboxylase

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Ferulic acid decarboxylases (Fdc) are decarboxylase enzymes capable of the reversible decarboxylation of aromatic carboxylic acids such as ferulic acid...

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Hydroxycinnamic acid

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acid Cinnamic acid – aloe Chlorogenic acid – echinacea, strawberries, pineapple, coffee, sunflower, blueberries Diferulic acids Coumaric acid Ferulic...

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Vanillic acid

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an intermediate in the production of vanillin from ferulic acid. The highest amount of vanillic acid in plants known so far is found in the root of Angelica...

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Chlorogenic acid

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hydroxycinnamic acids (caffeic acid, ferulic acid and p-coumaric acid) with quinic acid. Despite the "chloro" of the name, chlorogenic acids contain no chlorine...

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Vanillin

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and glyoxylic acid. Beginning in 2000, Rhodia began marketing biosynthetic vanillin prepared by the action of microorganisms on ferulic acid extracted from...

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Wheat beer

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character; its signature phenol is 4-vinyl guaiacol, a metabolite of ferulic acid, the result of fermentation by top-fermenting yeast appropriate for the...

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Arabinoxylan

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turn have ester-linked ferulic acid residues. These feruloyl units can undergo radical oxidative coupling forming ferulic acid dehydrodimers and possibly...

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Isoferulic acid

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Isoferulic acid is a hydroxycinnamic acid, a type of organic compound. It is an isomer of ferulic acid. Isoferulic acid can be found, amongst other compounds...

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Caffeic acid

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hydroxylation produces the caffeic acid ester of shikimic acid, which converts to chlorogenic acid. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl...

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Commelinids

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plants within the monocots, distinguished by having cell walls containing ferulic acid. The commelinids are the only clade that the APG IV system has informally...

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Sinapinic acid

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(H+) to the analyte of interest. Sinapic acid can form dimers with itself (one structure) and ferulic acid (three different structures) in cereal cell...

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Diferulic acids

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are formed by dimerisation of ferulic acid. Curcumin and curcuminoids, though having a structure resembling diferulic acids', are not formed that way but...

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Eleocharis dulcis

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and strengthened by certain phenolic compounds, such as oligomers of ferulic acid. This property is shared by other vegetables that remain crisp in this...

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Pittosporum tobira

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phenolic acids with caffeic acid being the most numerous (38.57 mg/g). The next most common phenolic acids were ferulic acid (20.07 mg/g), p-coumaric acid (12...

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Xylan

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contribute to cross-linking of cellulose microfibrils and lignin through ferulic acid residues. Xylans play an important role in the integrity of the plant...

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Eugenol

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caffeic acid by p-coumarate 3-hydroxylase using oxygen and NADPH. S-Adenosyl methionine (SAM) is then used to methylate caffeic acid, forming ferulic acid, which...

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Kalanchoe pinnata

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chalcones, taraxasterol, aurones, phenolic acid, caffeic acid, syringic acid, malic, oxalic and ferulic acid. Bufadienolides and phenanthrene are toxic...

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Navy bean

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growth. Furthermore, navy beans are the richest source of ferulic acid and p-coumaric acid among the common bean varieties. Dried and canned beans stay...

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Sodium ferulate

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Sodium ferulate, the sodium salt of ferulic acid, is a compound used in traditional Chinese medicine thought to be useful for treatment of cardiovascular...

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Bran

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level of dietary fiber (beta-glucan, pectin, and gum). It also contains ferulic acid, which is also a component of the structure of nonlignified cell walls...

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Silibinin

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give caffeic acid. The meta position alcohol is methylated by caffeic acid 3-O-methyltransferase to produce ferulic acid. From ferulic acid, the production...

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Corylus avellana

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kernels and its by-products are catechin, gallic acid, sinapic acid, caffeic acid, p-coumaric acid, ferulic acid, their esters and flavonoids.(Shahidi et al...

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List of antioxidants in food

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tomatoes. Produced from esterification of caffeic acid. Cinnamic acid and its derivatives, such as ferulic acid - found in seeds of plants such as in brown...

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Hydrocotyle sibthorpioides

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rosmarinic acid, chlorogenic acid, catechin, epicatechin, quercetin, biochanin A, rutin, gallic acid, ferulic acid, caffeic acid, ascorbic acid, and α-tocopherol...

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Miso

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than imported barley. Containing glutamic acid and aromatic compounds such as ferulic acid and vanillic acid, barley miso is distinguished by a characteristic...

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