2.1.3 Ferulic Acid
Synonyms Caffeic acid 3-methyl ether; 4-Hydroxy-3-methoxycinnamic acid.
Biological Sources Ferulic acid is widely distributed in small amounts in a variety of plants, namely: seeds of Citrullus colocynthis (L.) Schrad. (Cucurbitaceae)-Colocynth, Bilter Apple, Wild Gourd; flowers of Convallaria majalis L. (Liliaceae)-Lily-of-the-Valley; leaves of Digitalis purpurea L. (Scrophulariaceae)-Common Foxglove, Digitalis; young shoots of Equisetum hyemale L. (Equisetaceae)-Shavegrass, Great Scouring Rush; leaves of Euphorbia lathyris L. (Euphorbiaceae)-Mole Plant, Petroleum Plant, Caper Spurge; dried herb of Euphrasia officinalis L. (Scrophulariaceae)-Eyebright; gum-resin of Ferula assafoetida L. (Apiaceae)-Asafoetida; volatile oil of Gaultheria procumbens L. (Ericaceae)-Wintergreen, Teaberry, Boxberry; twigs of Hedera helix L. (Araliaceae)-Ivy; leaves of Hura crepitans L. (Euphorbiaceae)-Sandbox Tree; leaves of Plantago major L. (Plantaginaceae)-Plantain; volatile oil of Rheum officinale Baill. (Polygonaceae)-Chinese Rhubarb, Canton Rhubarb, Shensi Rhubarb; shrubs of Serenoa repens (Bartel.) Small (Arecaceae)-Saw Palmetto.
Preparation It has been isolated from Ferula foetida Reg. (Umbelliferae)* and from Pirus laricio Poir. (Abietineae)**. It may also be prepared by the interaction of vanillin, malonic acid and piperidine in pyridine for three weeks and then precipitating ferulic acid with dilute HCl.
Chemical Structure
Characteristic Features
cis-form : Yellow oil; uvmax (in ethanol): 316 nm.
trans-form : Orthorhombic needles obtained from water; mp 174°C UVmax (in ethanol): 236, 322 nm. It is soluble in hot water, ethanol and ethyl acetate; moderately soluble in ether; and sparingly soluble in benzene and petroleum ether.
Identification Test It forms the corresponding sodium salt by treatment with NaOH solution whereby the solubility gets enhanced appreciably.
Uses It is used as a preservative of food products.
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* Wolfrom et al. J. Agr. Food Chem., 8, 58 (1960).
** Krasemann, Arch. Pharm, 293, 721 (1960).
*** Fiedler, Arzneimittel–Forseh, 4, 41 (1954); Whiting, Carr, Nature 180, 1479 (1957), Guren, Chemical Abstracts, 61,
9965h (1964).
