27 May 2015
Yaroslav Naftulyev
Block B
Chemistry 11
Organic Project: Caffeine
Structural Diagram:
C8H10N4O2 or 1,3,7-trimethylxanthine
Chemical History:
Historically Caffeine has been discovered and used by different nations throughout the world. The
earliest recall of the use of Cocoa beans was recorded 600 B.C when Beans where found in a pot in a
mayan temple.It is said originally that the effect of Caffeine where observed when an Ethiopian farmer
named Kaldi moved his goats to a new pasture saw them to be restless after consuming beans, those
beans are today called cocoa beans. People then discovered that when those beans are boiled the
energizing effect is enhanced. This new discovery later to spread to Arabian countries and later on to
more industrialized countries. In the 15th century coffee has been used to help Priest in Yemen to stay
awake during prayer. Coffee houses were first opened in Egypt during the 16th century, later in Venice
and then Britain. The first introduction of Caffeine Europe was in 1573.
The first extraction was made by a German Chemist name Friedrich Ferdinand Runge who
isolated the compound. The first extraction with identification of Caffeine was made by a
German scientist named Emil Fischer in 1895. He also was able to synthesize the molecule in
1895 by extracting the molecule following this steps. He was effectively able to draw the
structural formula of Caffeine two years later. He received a Nobel Prize for being able to
extract the white powder from the beans.
Commercial Synthesizing Caffeine
''In this report, we wish to describe a simple synthesis of caffeine 7 from uracil 1
by Nmethylation, nitration, reduction, and cyclization reactions ''
''The reaction of uracil with excess of methyl iodide with potassium hydroxide and ethanol
(Method 1) or in an aqueous ethanol medium (Method 2) resulted in a very poor yield of 1,3dimethyluracil 2 (Sch. 1 and Table 1)''
''On the other hand, the presence of a strong base such as sodium hydride in
dimethylsulfoxide (DMSO), a nonaqueous solvent facilitates the methylation tremendously
(Method 3, Sch. 1)”
2. ''Conventional Nitration of 1,3-dimethyluracil 2 using a nitrating mixture of fuming nitric
acid and sulfuric acid''.
3.''The nitro group in compound 3 was reduced using iron and hydrochloric acid in
tetrahydrofuran (THF) to produce 5-amino-1,3-dimethyluracil ''.
4.''Heating compound 4 with formic acid generated in situ, the formamide derivative of
compound''.
5.''Nitration of the formamide derivative introduces a nitro group in position 6 of uracil to
produce compound 5 as a light yellow colored solid (see Sch. 2) ''.
6.''Reduction and intramolecular heterocyclization of compound 5 was simultaneously carried
out with iron and acetic acid to produce theophylline (75%)''.
7.''Theophylline was purified by flash chromatography on silicagel using ethyl acetate as the
solvent. The final step of the synthesis involves N-methylation at position 7 of theophylline
using method 3 to produce caffeine 7''.
Chemical and Physical Properties of Caffeine
Physical Properties:
Classification: xanthine (alkaloid compound)
Molecular Formula: C8H10N4O2
Systematic Name: 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione
Molar mass: 194.19 g mol/g
Appearances: Odorless, white powder
Chemical Properties:
Melting point: 238 °C
Boiling point: 178°C
Polarity: Polar
Solubility in water: Moderately Soluble at room temperature
Solubility in ethanol: Moderately soluble at room temperature
Density: 1.2 g/cm3
Effects and Side-Effects:
Caffeine is a chemical stimulant for the central nervous system and the metabolism. It reduces the
effect of drowsiness and restores awareness. This results in a better body coordination, increased focus
and increased mental flow. It also act as a stimulant for cardiac muscles and for the kidney (Urinate
more). One other use of Caffeine is to help premature children with breathing problem by giving them
citrated caffeine. Caffeine is effective at ''Stimulating the activity of the medullary, vagal, vasomotor,
and respiratory centers in the brain''.
Caffeine in the Society
Caffeine is a chemical that originates from a multitude of over 60 plants; its primary use is to make
coffee. Furthermore, it is also used in energy drinks, tea and even carbonated drinks like Coca-Cola.
Caffeine is also used in prescribed drugs such as pain relievers and cold relief medication.
Here is a common list of Caffeine products:
Problem with Caffeine:
Daily Consumption:
An active consumption of Caffeine creates tolerance adaptation because it creates more andenosine
receptors in the brain. When Caffeine is missing from the body, the receptors are missing the molecule
which leads to a feeling of headache. Furthermore, because the individual has more andenosine
receptors in the brain, the reduction of caffeine will cause the individual which causes an ''unwelcome
withdrawal symptom''.
Other symptoms such as nausea, headaches, fatigue, anxiety and even stomach ache. The body is
adaptation to the caffeine and because of this adaption the body will need more caffeine to return to the
''normal''. In addition, a consumption of caffeine leads to the loss of calcium and bone loss over time.
An extended use may cause osteoporosis.
Overuse and Overdose:
The overuse of the drug Caffeine pushes an individual to adhere a
condition called ''Caffeinism'' which includes symptoms such as
insomnia, irritability and nervousness. It can also cause gastric disease in the stomach. Overdose will
lead to similar symptoms as with use by with an increase risk of death. The overuse of Caffeine will
also cause sleep disorders in a condition called '' caffeine-induced sleep disorder .''
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References:
http://www.scienceofcooking.com/caffeine.htm
https://pubchem.ncbi.nlm.nih.gov/compound/caffeine#section=Top
http://www.umich.edu/~chemh215/CHEM216/Honors%20Cup_old/HCProposal/caffeine.pdf
http://udel.edu/~danikoll/history.htmlhttp://udel.edu/~danikoll/history.html
https://caffeineandyou.wordpress.com/historyandbackground/
https://myorganicchemistry.wikispaces.com/Caffeine