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Caffeine: M J Arnaud, Nestle S.A., Vevey, Switzerland

The document discusses caffeine, including its isolation from various plants in the 1820s-1840s and discovery in over 60 plant species. It was shown the isolated substances from coffee, guarana, and tea were identical. Caffeine's chemical structure is described and its physical properties including melting point, solubility, and ultraviolet absorption spectrum. Methods for determining caffeine in foods including UV spectrophotometry and HPLC are mentioned. The absorption, distribution and elimination of caffeine in the human body is briefly touched on.

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Verónica Morales-Félix
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68 views

Caffeine: M J Arnaud, Nestle S.A., Vevey, Switzerland

The document discusses caffeine, including its isolation from various plants in the 1820s-1840s and discovery in over 60 plant species. It was shown the isolated substances from coffee, guarana, and tea were identical. Caffeine's chemical structure is described and its physical properties including melting point, solubility, and ultraviolet absorption spectrum. Methods for determining caffeine in foods including UV spectrophotometry and HPLC are mentioned. The absorption, distribution and elimination of caffeine in the human body is briefly touched on.

Uploaded by

Verónica Morales-Félix
Copyright
© Attribution Non-Commercial (BY-NC)
Available Formats
Download as PDF, TXT or read online on Scribd
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C

CAFFEINE
M J Arnaud, Nestle S.A., Vevey, Switzerland
2005 Elsevier Ltd. All rights reserved.

During the period 18201827, three white crystalline substances called caffein or coffein, guaranin, and thein were isolated from green coffee beans, guarana, and tea, respectively. These substances were shown in 18381840 to be identical. Later, caffeine was also discovered in mate prepared from Ilex paraguariensis and kola nuts. Since then, caffeine has been shown to be a natural constituent of more than 60 plant species. Two other related compounds, theophylline and theobromine, have also been isolated from tea and cocoa beans, respectively while a third, paraxanthine, was isolated from human urine (Figure 1). By the end of the nineteenth century, all of these methylated xanthines had been synthesized. Caffeine, both natural and synthetic, has been used as a flavoring agent in food and beverages and as an active component of a variety of over-the-counter pharmaceutical products and drugs. A regulation adopted by the European Commission requires the compulsory labeling high caffeine content when soft drinks contain more than 150 mg caffeine per liter. In addition to natural caffeine obtained by the industrial decaffeination process, caffeine can also be obtained by the methylation of theobromine and also by total chemical synthesis using dimethylcarbamide and malonic acid.

considerably increased at higher temperatures (1% (w/v) at 15  C and 10% at 60  C). Its melting point is 234239  C and the temperature of sublimation at atmospheric pressure is 178  C. Caffeine is a very weak base, reacting with acids to yield readily hydrolyzed salts, and relatively stable in dilute acids and alkali. Caffeine forms unstable salts with acids and is decomposed by strong solutions of caustic alkali. In aqueous solution, caffeine is nonionized at physiological pH. Dimers as well as polymers have been described. The solubility of caffeine in water is increased by the formation of benzoate, cinnamate, citrate, and salicylate complexes. In plants, chlorogenic acid, coumarin, isoeugenol, indolacetic acid, and anthocyanidin have been shown to complex with caffeine. Caffeine exhibits an ultraviolet absorption spectrum with a maximum at 274 nm and an absorption coefficient of 9700 in aqueous solution. Upon crystallization from water, silky needles are obtained containing 6.9% water (a 4=5 hydrate).

Determination
Caffeine has traditionally been identified in foods by ultraviolet spectrophotometry of an organic solvent extract after suitable cleanup by column chromatography. Such methods tend to be laborious and may be subject to interference from other ultravioletabsorbing compounds. Recently, high-performance liquid chromatography has been more extensively used. This technique, often in conjunction with solid phase extraction, can provide accurate data for the determination of caffeine in foods and physiological samples.

Chemistry
Caffeine (Mr 194.19) is also called, more systematically, 1,3,7-trimethylxanthine, 1,3,7-trimethyl-2,6dioxopurine, or 3,7-dihydro-1,3,7-trimethyl-lHpurine-2,6-dione and has been referred to as a purine alkaloid. Caffeine is odourless and has a characteristic bitter taste. It is a white powder (density (d18=4) 1.23) moderately soluble in organic solvents and water. However, its solubility in water is

Absorption, Distribution, and Elimination


Following oral ingestion, caffeine is rapidly and virtually completely absorbed from the gastrointestinal tract into the bloodstream. Mean plasma

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