Ferulic Acid

Title: Ferulic Acid
CAS Registry Number: 1135-24-6
CAS Name: 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid
Additional Names: 4-hydroxy-3-methoxycinnamic acid; 3-methoxy-4-hydroxycinnamic acid; caffeic acid 3-methyl ether
Molecular Formula: C10H10O4
Molecular Weight: 194.18
Percent Composition: C 61.85%, H 5.19%, O 32.96%
Literature References: Widely distributed in small amounts in plants. Isoln from Ferula foetida Reg. Umbelliferae: H. Hlasiwetz, L. Barth, Ann. 138, 61 (1866); from Pinus laricio Poir. Abietineae: M. Bamberger, Monatsh. Chem. 12, 441 (1891); see also Beilstein 10, 436 (1927) and supplements. Prepd by the interaction of vanillin, malonic acid and piperidine in pyridine for 3 weeks, then precipitating with HCl: Vorsatz, J. Prakt. Chem. 145, 265 (1936); Pearl, Beyer, J. Org. Chem. 16, 216 (1951). Sepn of cis and trans isomers: Comte et al., Compt. Rend. 245, 1144 (1957). 13C NMR study: C. J. Kelley et al., J. Org. Chem. 41, 449 (1976). Discovery as a component of cell walls in wheat and barley: M. G. Smart, T. P. O'Brien, Aust. J. Plant Physiol. 6, 485 (1979). Use as food preservative: T. Tsuchiya, M. Takasawa, JP Kokai 75 18621 (1975 to Kyokuto Shibosan), C.A. 83, 7602v (1975).
Derivative Type: cis-Form
Properties: Yellow oil. uv max (alcohol): 316 nm.
Absorption maximum: uv max (alcohol): 316 nm
Derivative Type: trans-Form
Properties: Orthorhombic needles from water, mp 174°. uv max (alcohol): 236, 322 nm. Sol in hot water, alcohol, ethyl aetate. Moderately sol in ether. Sparingly sol in petr ether, benzene. Forms a sodium salt.
Melting point: mp 174°
Absorption maximum: uv max (alcohol): 236, 322 nm
Use: Food preservative.
Ferumoxides Ferumoxsil Ferumoxtran 10 Fervenulin Fexofenadine

Ferulic acid
Ferulic acid acsv.svg
Identifiers
CAS number 1135-24-6 YesY
PubChem 445858
ChemSpider 393368 YesY
DrugBank DB07767
ChEBI CHEBI:17620 YesY
ChEMBL CHEMBL32749 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H10O4
Molar mass 194.18 g/mol
Appearance Crystalline Powder
Melting point 168–172 °C
Hazards
NFPA 704
NFPA 704.svg
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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).