Title: Ferulic Acid
CAS Registry Number: 1135-24-6
CAS Name: 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid
Synonyms: 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.
