Organic Chemistry in Nature
Chemistry 312 - Organic
at Virginia Wesleyan College
Research Essay Project
The natural source of the organic compound is described, as well
as the primary uses for the compound. A brief explanation of its
purification from its natural source and/or its laboratory synthesis is
included. Resources are listed below the compound's information. The
structures were made using the ChemSketch program from ACD Lab
Acid - Kevin Cartwright
acid or vitamin C (L-3-ketothreohexuronic acid lactone) is essential to our
lives. It has the chemical formula
C6H8O6 and a molecular weight of 176.12g/mol.
The hydroxyl groups and the other oxygen atoms give it a melting point of
They also allow it to be acidic and soluble in water and other polar
solvents. Vitamin C is used as a
coenzyme in the production of collagen. It
is also thought to be a helpful tool to the immune system also.
Ascorbic acid was first isolated from citrus fruits in 1932, but it had been
known about since James Lind found that citrus fruits prevent scurvy in the
1700s. There are two pathways for
the synthesis for ascorbic acid. They
both begin with D-glucose. One is
the inversion pathway and uses the L-Galactono-1, 4- lactone dehydrogenase. The
second pathway is the non-inversion pathway and uses the enzyme sorbosone
- Kim Campbell
is the simplest representative of the aromatic aldehydes.
It is found in cherries, almonds, apricot and peach pits. It is found in nature as the glycoside amygdalin, which is a
sugar derivative of the cyanohydrin of benzaldehyde that is found in bitter
almonds. It was first isolated in
1803. Benzaldehyde is best known as
being artificial essential oil of almond but it has many other uses such as; the
manufacturing of dyes perfumes, flavorings, cinnamic and mandelic acids, and it
is also used as a solvent. It is
synthesized in laboratories from toluene being chlorinated to benzyl chloride or
by direct oxidation of toluene with manganese dioxide.
Some more recent developments in the use of benzaldehyde are for the
health and agriculture industries. Benzaldehyde
is being used as a pesticide and also as an anticancer agent. These uses are
still in development but would be very helpful in solving some of these problems of today.
- Lisa Fusco
is a white, crystalline powder with a bitter taste that can be found naturally
in many different plants. For
thousands of years natives of Asia, South America and Africa have used these
plants, because they contained caffeine. In
Africa, upper class tribal members would chew Kola nuts and coffee beans because
the affects would increase their energy for long hunts and hindered the pain of
weary bodies. In South America, the
coca plant and coffee beans were chewed upon because the caffeine would stop
hunger pains and for the natives of the mountain regions, they ate these
caffeine enriched plants to raise their heart beat and thus their body
temperature. In Asia, tea was a
favorite of the people because it was said to sharpen their mental skills and
prolong attention in challenging subjects.
Caffeine is still used to do all these things.
It is known as the perfect "stay awake" drug and is also used
by doctors to accompany perscriptions, such as antihistamines and painkillers
that can make the patient drowsy. It targets the central nervous system by
stimulating the body in all the ways that natives from South America, Africa and
Asia believed they did. However,
when too much is taken, insomnia, irritation, headaches and anger can result.
is addictive and can be found in most sodas, tea, chocolate, coffee and cocoa. Caffeine is added to most of these products in the powdered
form after it is extracted from tea, or coffee.
It is removed by first boiling it in water, in which it is highly
soluble. Then, after a concentrated
mixture is created, the tanins of the tea or coffee (the colored components) are
separated from the caffeine by doing three extractions with dichloromethane,
in which it is even more soluble. The crude product is dried and then
sublimed to complete the purification. The
caffeine crystals are then collected and can be put in a pill form or mixed into
a soft drink.
Kenneth L. "Macroscale and Microcale Organic Experiments";Houghton
Mifflin Company: Boston,1999;third edition,146-150.
- Troy Shell
A was found in the extract of Calophyllum lanigerum var. austrocoriaceum,
which exists in the Malaysian rainforests (2).
The National Cancer Institute found Calanolide A to be remarkably
effective against HIV-1, the most common strain of the AIDS virus in the Western
world (3). Today,
Calanolide A is in the developmental drug phase and is a member of the HIV drug
class of non-nucleoside reverse transcriptase inhibitors (4).
Calanolide A blocks transcription of the viral RNA into DNA within the
host cell’s cytoplasm, therefore preventing replication of the HIV virus (5).
The synthesis of Calanolide A begins with a triphenol (6).
There are four ring-building reactions, one of which is a Friedel-Crafts
acylation, followed by a reduction from a ketone to an alcohol in the fifth and
final reaction of the synthesis (6).
Unlike many HIV drugs, Calanolide A produces mainly mild and temporary
side effects (4).
For the most up-to-date information on the development of Calanolide A as
an HIV drug, go to http://www.sarawak-medichem.com.
Sarawak Medichem Pharmaceuticals, Inc.
‘Sarawak Medichem Pharmaceuticals Home Page’ http://www.sarawak-medichem.com
(April 9, 2001)
Diamond, N. “Tropical
delight, disaster, and discovery: finding cures among the wreckage of a
hurricane” Omni 1994,
16 (8), 22.
Shenon, P. “Hunt
in forests of Borneo aims to track down natural drugs” New York Times (Late
New York Edition)
1994, December 6, C4.
Sarawak Medichem Pharmaceuticals, Inc.
‘The Unique Features of Calanolide A’ http://www.sarawak-medichem.com/cala/calafeat.htm
(April 9, 2001)
(April 9, 2001)
Chenera, B., M. West, J. Finkelstein & G. Dreyer.
“Total synthesis of (±)-Calanolide A, a non-nucleoside inhibitor
of HIV-1 reverse transcriptase” Journal of Organic Chemistry 1993,
- Stephanie Dodgers
Dopamine is an important neurotransmitter
located in the substancia nigra part of the brain.
Dopamine has a molecular formula of C8H11NO2
and a molecular weight of 153.18 g/mol. Dopamine
is a member of the catacholamine family, which has a characteristic benzene ring
with hydroxyl groups in the third and fourth positions.
Alterations of the dopamine content in the brain are responsible for many
severe neurological disorders such as schizophrenia, Parkinson’s disease, and
Tourette’s syndrome. Dopamine was
first recognized as a neurotransmitter in the late1950’s.
In the following years, much research was done by Carlsson, Kandel, and
Greengard linking dopamine to the mentioned disorders as well as pinpointing
dopamine’s exact function. The
scientists won the Nobel Prize in physiology or medicine in 2000 for their
research. Dopamine can be purified
from dopamine neurons and nervous tissue. This
isolation and purification has been performed in laboratory rats, bovine, and
humans. Dopamine is synthesized in
vivo through several enzyme-catalyzed reactions beginning with the amino acid
tyrosine. However, in the
laboratory, dopamine is made from an enzyme-catalyzed reaction between L-Serine
and Pyrocatechol. The discovery and
understanding of dopamine has been extremely beneficial to society in furthering
our understanding of the brain and neurological disorders.
Nash, J. Madeline "Not So Dopey Dopamine" http://www.time.com/time/magazine/printout/0,8816,57762,00.html,
April 11, 2001.
April 11, 2001.
- Craig O'Neill
Ethanol has been used for centuries.
There is no exact record of its discovery.
However, it is known to have been used by the Arabs and monks in the
early 1200’s. Ethanol is a simple
Ethanol has many names, which range from ethyl alcohol,
absolute alcohol, anhydrol to ethyl hydrate. The molecular weight is 46.088 g/mol and the density is 0.789
g/mL. Ethanol has an extremely low
melting point, -114.1oC. The
boiling point is 78.3oC, because ethanol is capable of hydrogen
bonding with itself. Ethanol is
used as solvent, extraction medium, antiseptic,sedative, and an alcoholic
beverage, as well as a component or in the manufacture of perfumes (because of
its ability to evaporate quickly), pharmaceuticals, lacquers, plastics,
cosmetics, rubber, mouthwash, aerosols, antifreeze, and dehydrating agents. Ethanol can be synthesized using ethylene. Ethylene
undergoes an acid-catalyzed hydration. A
H+ ion is added to the double bond forming a carbon with a positive
charge. The oxygen from a water
molecule donates a pair of electrons to this carbon.
The water molecule now has the positive charge.
In order to regain its neutral status, it sheds a hydrogen
to form ethanol.
Salzberg, Hugh W., From Caveman to Chemist; American Chemical
Society, Washington, DC, 1991
- John Tomasheski
Pyrolysis, or a technique of applying high heat to organic
matter in the absence of air or in reduced air, is an ancient method of
producing methanol. Ancient
Egyptians used pyrolysis, otherwise known as wood distillation, to produce tars
and other chemicals used for embalming. Despite
this ancient production of methanol, the simple alcohol was not officially
discovered until 1661 by Robert Boyle.
Within society, methanol serves many purposes.
Currently, methanol is being studied to learn its advantages over
gasoline as an automotive fuel. It
is also used as automotive antifreeze because of its low freezing point, as well
as rocket fuel and a general solvent for many experiments and compounds.
The modern method for synthesizing methanol involves the direct combination of
carbon monoxide gas and hydrogen gas in the presence of a catalyst, ZnO-Cr2O3.
The reaction also takes place under high pressure, between 300 – 400
atmospheres, and a high temperature of 300 – 400oC. In contrast
with the impure product obtained by wood distillation, synthetic methanol is a
chemically pure material.
L. “Energy Farming in America”.
- Devenia White
is a hormone that stimulates uterine contractions and lactation in pregnant
females. This hormone is produced naturally by the female in her posterior
pituitary gland. This gland is located at the base of the back of the brain. (1)
Once the strong uterotonic agent has caused uterine muscle to expel the baby
from the mother’s womb, more oxytocin is released when the infant begins to
suck on its mother's breast. (2) The release of the oxytocin in the breasts
causes myoepithelial cells, which surround the alveoli, in the mammary glands to
contract and excrete milk. (2) During labor, this hormone also causes higher
blood pressure and less urine formation. (3) Oxytocin is commercially used to
induce labor in pregnant females when the unborn child is at risk and the mother
has not yet produced this hormone herself.
Between 1909 and 1911 Sir Henry Hallet Dale discovered and extracted oxytocin in
and from the pituitary gland. (1,4) Oxytocin was also extracted from gonads,
placenta, adrenal glands, uterus, and male accessory glands. (5) Oxytocin’s
synthesis goes through multiple steps, essentially it is a peptide synthesis
involving a series of condensation reactions forming amide bonds. Oxytocin
is also modified to form the cyclic configuration. This compound was then
oxidized by exposure to air. (6) During oxidation, the hydrogens that are
attached to the sulfur were released and the two sulfurs reacted to form a
disulfide bond. The final product of this lengthy synthesis was C43H66N12O12S2,
better known as oxytocin.
Cushing, Harvey, “The
Role of the Pituitary Gland” http://www.medivisionindia.com/eureka/1912.phtml,
Dreifuss, J.J., “Oxytocin in Reproductive Biology: Newly Discovered
Sites of Production and of Action” http://matweb.hcuge.ch/matweb/
endo/Reproductive_health/ Oxytocin_ in_ reproductive biology.html, 04-09-01.
Williams, “Endocrine Glands” http://www.geocities.com/Athens/Parthenon/6853/glands.html,
“Dale, Sir Henry Hallett” http://www.fwkc.com/encyclopedia/low/
articles/ d/ d006001634f.html, 04-09-01.
“ Reproductive Hormones” http://www.uwyo.edu/ag/anisci/wjm/repro/rephorm.htm,
Du Vigneaud et al., “The Synthesis of Oxytocin” Journal of the
American Chemical Society 1954, vol. 76 no. 9, pp 3115-3121.
Phosphate - Courtney Cornwell
phosphate, or vitamin B6, plays an important role in many functions of the body.
It maintains proper function of nerves and the brain, as well as chemical
balances. It was discovered through
nutritional experiments in which lab rats were fed vitamin-deficient diets.
It is a part of many different reactions, such as racemization of
stereoisomers to make cell walls in bacteria and transisomerization.
It is a part of the aldehyde family, but because of the nitrogen, it is
also an imine. It absorbs
ultraviolet light at 390 nm in alkaline solutions, but only 295 nm in acidic
solutions. It is a water-soluble
vitamin, which can lead to major defects in the body if too little or too much
of it is present. Vitamin B6
deficiency can lead to impaired neural functioning that can sometimes be reversed, but only after months or years.
- Sara Simms
Quinine's systematic name
is (8a,9R)-6'-methoxycinchonan-9-ol. It has been primarily used to treat
malaria, and even though other synthetic treatments have been produced, it is
still used to treat strains that are drug resistant. Quinine is also used
to relieve nighttime leg cramps, although the means by which it does this is
still unclear. Quinine was first discovered in South America in the 1600's, when
Spanish explorers and missionaries used the bark of the Cinchona tree as
medicine. Peruvian Jesuits introduced quinine to Europe in 1640, in the form of
a white powder from the bark. Destruction of the cinchona trees, because of the
demand for quinine, made them very rare, so a synthesis method of producing
quinine from coal tar was discovered by Robert Woodward and William Doering in
1944. Quinine is synthesized by the Mannich Reaction, as ferrocene is converted
to dialkylaminomethyl ferrocene by methanol and a dialkylamino (or piperidine).
Condensation with formylquinoline produces quinine, which has two chiral
J. et al. "US Patent and Trademark Office - United States Patent 6,127,543:
Antimalarial organometallic iron complexes" http://www.uspto.gov/patft/index.html
Acid - Melissa Downs
acid, or butanedioic acid, is an organic compound that was originally observed
in nature within all plant and animal tissues. It plays a significant role in
their intermediary metabolism and the Kreb's Cycle (1).
However, scientists could not come up with a way to purify the succinic
acid from the plant and animal tissue in which they observed it.
Then, in the 19th century, German, Swedish, an Swiss chemists recognized
that succinic acid was present in amber, a translucent fossil resin (or waste
secretion) which comes from trees. Amber
was believed to contain 3-8% succinic acid, which was formed from the
micro-organism induced fermentation of the cellulose present in the resin (2).
The succinic acid was then later purified for the first time through the
distillation of the amber resin.
Today, succinic acid can also be synthesized in the laboratory.
This can be done in two ways. The
conventional way to do this is to start with n-butane and oxidize it to maleic
anhydride. The maleic anhydride is
then hydrated to maleic acid, and the maleic acid is hydrogenated to yield the
succinic acid. The second synthesis costs less money and is actually good for
our environment. Not only does this
synthesis eliminate a lot of the waste that is produced as byproducts in the
conventional synthesis, but it also uses a renewable agricultural starting
compound, corn. Using corn as a
starting compound also gives our agricultural industry a new, expanded market in
the economy. To start the
synthesis, a microorganism produces succinic acid in high yields by fermenting
glucose sugar from the corn. Next, Advanced Membrane Separation Technology separates and
purifies the acid. At this Point
the pure succinic acid can now be turned into chemicals to be used for
production of other important products by industries (3).
Succinic acid is primarily used today directly as a flavoring agent for food and
beverages. Also, indirectly it can be used as an intermediate for dyes,
perfumes, lacquers, and in vehicle water cooling systems and the manufacturing
of clothing, paint, inks, and fibers (4).
2-"Physical Properties of Amber" http://www.emporia.edu/earthsci/amber/physic.htm,
3-"Biotechnology at Argonne National Laboratory" http://www.ipd.anl.gov/biotech
4-"Parchem Trading Ltd.-Succinic Acid-Chemical Pharmaceutical
Foods" http://www.par-chem.com/products/succinic.html, 4/07/01.
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