Bibliography

1. F. J. Francis, "Miscellaneous Colorants," in G. A. F. Hendry and J. D. Houghton, eds., Natural Food Colorants, Blackie, Glasgow, Scotland, 1992, pp. 242-272.

2. F. J. Francis, "Polyphenols as Natural Food Colorants," in A. Scalbert, ed., Polyphenolic Phenomena, INRA, Versailles, France 1993, pp. 209-220.

3. F. J. Francis, Handbook of Food Colorant Patents, Food and Nutrition Press, Westport, Conn., 1986.

4. J. B. Harborne, The Flavonoids: Advances in Research Since 1980, Chapman and Hall, London, 1988.

5. G. Mazza, "Anthocyanins in Grapes and Grape Products," Crit. Rev. Food Sci. Nutr. 35, 341-371 (1995).

6. F. J. Francis, Handbook of Food Colorants, Eagen Press, St. Paul, Minn., 1998.

7. D. Amic, J. Baranac, and V. Vukadinovic, "Reactivity of Some Flavylium Cations and Corresponding Anhydrobases," J. Agric. Food Chem. 38, 936-940 (1990).

8. P. Bridle, K. G. Scott, and C. F. Timberlake, "Antocyanins in Salix Species. New Anthocyanin in Salix purpurea Bark," Phytochemistry 12, 1103-1106(1973).

9. H. Fulcrand et al., "A New Class of Wine Pigments Generated by Reaction Between Pyruvic Acid and Grape Anthocyanins," Phytochem. 47, 141-147 (1998). 10. P. Sarni-Manchado et al., "Stability and Color of Unreported Wine Anthocyanin-Derived Pigments," J. Food Sci. 61, 938941 (1996).

COLORANTS: ANTHRAQUINONES COCHINEAL AND CARMINE

Cochineal extract is a very old colorant with references as far back as 5000 B.C. when the Egyptian women used it to color their lips. It was introduced to the Western world by Cortez when he found it in Mexico in 1518. The Aztecs had been using it for many years, and the native Mexicans were cultivating the cochineal insect on the aerial parts of cactus, Opuntia and Nopalea species, particularly N. coc-cinelliferna. The Spaniards guarded the secret of cochineal jealously, and by 1700 as much as 500,000 pounds of cochineal were being shipped to Spain from Mexico each year. This is impressive when one considers that it takes 50,000 to 70,000 insects to produce 1 lb of colorant. Other areas, including the East and West Indies, Central and South America, Palestine, India, Persia, Europe, and Africa, developed the ability to produce cochineal. The cochineal trade peaked in 1870 and then declined rapidly due to the introduction of the synthetic colorants in 1856. Peru today is the major supplier with an annual production of about 400 tons. This constitutes 85% of the world production with Mexico and the Canary Islands sharing the remaining 15%.

American cochineal is the most significant form today, but there are other sources. Similar pigments are produced by insects from the families Coccoidea and Aphidoidea and have various historical names. Armenian Red is obtained from the insect Porphyrophera hameli, which grows on the roots and stems of several grasses in Ajerbaizan and Armenia. Polish cochineal is obtained from the insects Margaroides polonicus or P. pomonica found on the roots of Scleranthus perennis, a grass found in Central and Eastern Europe.

Cochineal and its derivatives are staging a comeback today as a food colorant because of their superior technological properties and the influence of the "natural" trend.

Chemistry

Cochineal extract (CI Natural Red 4, CI No. 75470, EEC No. E 120) is extracted from the bodies of female insects, particularly Dactylopius coccus Costa, just prior to egg laying, at which time the insects may contain as much as 22% of their dry weight as pigment. One may wonder at the biological significance of this, but presumably it is a protection from predators. Historically the insects were extracted with hot water, and the colorants were known as "simple" extracts of cochineal. Later methods involved extraction with aqueous alcohol. After removal of the alcohol, the preparation, called cochineal extract, contains approximately 2 to 4% carminic acid (Fig. 1) as the main colorant

OH 0 CH3 OH O CH3

OH 0 CH3 OH O CH3

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