Acid - Natalia Sepulveda
acid, commonly referred to as Vitamin C, was discovered in 1912 and isolated in
1933 from lemons. The compound was first chemically synthesized in 1933 from a carbohydrate
precursor via a method called the Reichstein process. This particular chemical
synthesis is a mixed fermentation/chemical synthesis, whereby; sorbitol is first
oxidized into sorbose by fermentation and then transformed into DAKS (di-acetone-ketogulonic
acid) in a two stage chemical process. In
subsequent steps, the DAKS is dissolved in a mix of organic solvents and its
structure is rearranged to form Vitamin C, using an acid catalyst. The crude Vitamin C is then purified by recrystallization. The newer
method of chemical synthesis utilized today employs the same first step as the
Reichstein process, but in the two stage fermentation process, a second step
replaces the chemical reactions used to produce DAKS which results in a
different intermediate, KGA. This
newer method makes use of less toxic chemical agents and decreases waste costs.
L-ascorbic acid is biologically synthesized in plants and some mammals
through different pathways not clearly understood. It can be found in many vegetables such as broccoli, bean
sprouts, cauliflower and fruits such as oranges, kiwi strawberries (most citrus
fruits). The compound is used today
as an antioxidant in the synthesis of collagen and many of its derivatives are
used as anti-cancer drugs. It is an
essential vitamin that prevents Scurvy, heart disease, cerebral palsy (and many
more diseases) and used in the treatment of AIDS.
“The Natural History of Ascorbic Acid in the
Evolution of the Mammals and Primates and Its Significance for Present Day
Man” from Orthomolecular
Psychiatry, 1972, Volume
1, numbers 2 &3 , pp. 82-89.
- Cherie Cannady
is one of the most popular drugs on the market today. It is a powerful stimulant
to the central nervous system (CNS). Millions of people consume the product
everyday, probably without even knowing it. It is found in tea, coffee, kola,
cocoa, and guarana. The Chinese first discovered the effects of caffeine in the
form of medicinal tea about five thousand years ago, for the purpose of staying
awake. The active ingredient in coffee and tea was not identified until the
nineteenth century (1). It wasn’t until 1820 that caffeine was truly
discovered (2). The reason is that the separation of caffeine from a plant is
more difficult than just a simple distillation. There are many steps required
and the use of a strong solvent (2). There are four processing methods used to
remove caffeine from these natural resources: methylene chloride, ethyl acetate,
carbon dioxide, and water processing (3,4). There are many ways to
chemically synthesize caffeine in the laboratory. Synthetic caffeine is mainly
produced by the chemical synthesis of urea as the basic raw material (5).
Caffeine containing plants are used in beverages or herbal materials, more than
any other plants. Most people today use it for energy purposes, because it
increases mental alertness, which is needed to stay focused (6). Much
information has proven that caffeine can actually be a very harmful drug if too
much is consumed. It is a mood altering and addictive compound. It can cause
nervousness and insomnia (7).
1. Braun, Stephen. “Buzz: The science and lore of
alcohol and caffeine.” New York, NY.
Oxford University Press, 1996.
2. The World of Caffeine.www.business2.com/images/mag/caffeine.pdf.
Bennett Weinberg, A. March 4, 2003.
3. How Stuff Works.http://home.howstuffworks.com/caffeine1.htm.
“How Caffeine Works.” Brain, M. March 5, 2003.
4. American Chemical Society. http://www.cas.org/portal/vhemistry?PID.
“How’d They Do That? Making Decaf Coffee.” Polittle, James. April 4, 2003.
5. Shri Ahmsa Mines and Minerals LTD. www.naturalcaffeine.com/caffeine.
“Natural Caffeine” April 23, 2003.
6. MEDLINEplus Drug Information. www.nlm.nih.gov/medlineplus/drugino/uspdi/202105.html#Brands.
March 4, 2003.
7. Wang, X. “The Psychopharmacology of Herbal
Medicine: Plant Drugs that Alter Mind, Brain, and Behavior.” Journal of
Natural Products 2002, 65(1), 92-93.
- Kim Mulholland
Galactose is known as a monosaccharide, which is
a carbohydrate that cannot be “hydrolyzed to a simpler carbohydrate”. Galactose is the direct product of the photosynthetic combination of
carbon dioxide and water. Galactose
naturally occurs in the body’s brain and nervous tissue, ivy berries and
grains, and coffees. It is used in
milk chocolate confectionary products, laxatives, and sports drinks. However it is more widely used in its combination with glucose to form
the disaccharide dairy sugar lactose. Lactose
is crystallized in a laboratory from milk. The crystals of lactose are collected by suction filtration and washed
with small amounts of cold ethanol. In lactose, glucose and galactose are
connected by a beta-1,4-glucosidic bond. The
enzyme, beta-galactosidase, otherwise known as lactase, hydrolyzes the
beta-1,4-glucosidic bond and breaks down lactose into its two simple sugar
components, glucose and galactose.
- Tom Drabczyk
Organic Germanium was discovered in an attempt to synthesize
germanium into an organic compound. The idea was to use it for therapeutic
reasons. The first compound created was carboxyethylgermanium sesquioxide. Today
it is used for multiple treatments of medical conditions, such as arthritis,
cancer, leukemia, diabetes, pan, and malaria. Its also used a dietary
supplement. In lab this compound is created by a hydrolysis of an
- Dan Burrell
is natural substance that was isolated around the early 1500’s for purported
uses to cure rheumatism. Though it has since been proven ineffective on
rheumatism, it is at present, a widely used cough expectorant in nearly every
cough, cold, flu, and allergy medication on the market. The extraction
from the natural source is involves a very simple steam distillation process
followed by a series of acid-base extractions to remove the guaifenesin resin
from the other substituens in the distillate. As with most natural
ingredients, the natural extraction processes are not efficient enough, or the
compound simply isn’t abundant enough from its natural sources for a
large-scale distribution. Thus, synthetic processes must be designed to
obtain the needed compound. For the laboratory synthesis of guaifenesin, a
simple Williamson ether synthesis reaction will provide the desired product,
retaining the stereochemistry of the original stereo reactant,
3-chloro-1,2-propanediol. The first reactant, o-methoxyphenol, is
dissolved in ethanol and refluxed with 6.25M solution of sodium
hydroxide, a strong base. This serves to deprotonate the phenyl ring to
give the highly reactive phenoxide ion. The second reactant,
3-chloro-1,2-propanediol, is also dissolved in ethanol and then added to the
reaction mixture after the period of refluxing. The ethanol is an aprotic
solvent that aids in reducing the competing E2 mechanism and is also is a
solvent that is easily removed by vacuum filtration. Washing the
precipitated product with water and making several extractions of the aqueous
layer serves to remove the formed NaCl and recrystallizing the organic layer
from ethyl acetate with hexanes provides the racemically pure product.
Pure guaifenesin appears as a white crystalline powder, that with further
analysis is revealed to be minute rhombic prisms.
Dicks, A. P.; Stabile, R. G. “Semi-Mcroscale Williamson Ether
Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets.”
Journal of Chemical Ecducation. March
2003. Vol. 80 No. 3.
2. Jenner, Frank. “Section I: Guiaifenesin.” http://www.cfs-recovery.org/guaifenesin.htm.
March 25, 2003.
- Stefanie Lake
Isopentyl acetate and isoamyl acetate are the common names for
3-methylbutyl acetate. This compound was first discovered as one of the
alarm pheromones of honeybees (1). It was later found in and purified from
yellow passion fruits, pears, apples, and Zanthoxylum simulans fruits
(2). Isopentyl acetate is sometimes called banana oil, due to its
banana-like flavor and smell. When isopentyl acetate is diluted it has
more of a pear-like odor and taste. It is primarily used as a flavoring
agent in various foods and drinks, such as honey, butterscotch, artificial
coffee, and alcoholic beverages (3). Isopentyl acetate is also found in
perfumes. The primary way of synthesizing this ester is through Fischer
esterification. The reactants involved in this reaction are isopentyl
alcohol and acetic acid. Fischer esterification is the nucleophilic
addition of isopentyl alcohol to the carbonyl group of the protonated acetic
acid. Nucleophilic addition is followed by elimination of a proton.
An unstable tetrahedral intermediate forms. This intermediate undergoes
dehydration and reforms the carbonyl group. Reformation of the carbonyl
group forms the isopentyl acetate. Purification of the crude isopentyl
acetate is achieved through simple distillation. Simple distillation is a
process used to separate two immiscible liquids (4).
Almeida, Balderrama, and Giurfa “Alarm pheromone induces stress analgesia via
am opioid system in the honeybee” Physiological Behavior 1997.
2. Chyau, Mau, and Wu
“Characteristics of the Steam-Distilled Oil and Carbon Dioxide Extract of
Zanthoxylum simulan Fruits” Journal Agriculture Food Chemical.
3. “History of Isoamyl Acetate”
4. “The preparation of Isopentyl
acetate (Banana Oil)” http://servercc.oakton.edu/~maas/223Labex.html
- John Shannon
is a compound that was found to occur naturally in Caramel, Chicory, Cocoa,
Coffee, Milk, Roasted Malt, Strawberry, and Bread. When added to a broad group
of substances, it increases and sustains their sweetness and fragrance (1).
Maltol is used to formulate essences for food, cigarette and similar kinds of
consumables. It is extensively used in food, beverage, tobacco, brewery,
cosmetics and pharmaceuticals industries (2). The smell is often referred to as
that of cotton candy and plays an important role in commercial fruit flavoring.
Maltol is synthesized by liquid-liquid extraction. In the
liquid-liquid extraction of maltol, the process is performed between a
water-rich liquid phase and a hydrophilic organic solvent-rich liquid phase (3).
“Burnt Sugar” http://www.leffingwell.com/burnt.htm
March 27, 2003
April 22, 2003
Till Adrian, Jörg Freitag, and Gerd Maurer American Chemical
Society 2001 Sept; 4990 -4997http://pubs.acs.org/cgi-bi
- Courtney Cornwell
Norethindrone was originally found as a hormone in the human body
that suppressd vaginal cornification and estrous cycles during research
involving menopausa l women. It has been used as a progestational oral
contraceptive among breast-feeding women because it does not affect breastmilk.
The laboratory synthesis of norethindrone includes esterification of an alcohol
followed by oxidation and ethylation.
1. DiNunno, C.M. et al
“7alpha-methylnorethindrone enanthate 10beta-hydroperoxide: isolation and
characteristics” Steroids 1983, Volume 42(No. 4),
2. Rao, P.N. “Preparation of 9alpha, 11sigma-tritiated
17alpha-ethynylestradiol, mestranol, estradiol-17 beta, and norethindrone”
Steroids 1971 Volume 18 (No. 2), 219-229.
II - Alena Quigg
II is an extraction from the Pyrethrum flower. This flower has been used
for thousands of years as an insecticide. During the 18th
century, it became part of a large trade market, leading to an increased desire
to discover the identity of the extract’s components. Directed
fractionation led to the discovery of Pyrethrin II’s identity in the
mid-1900’s. See the attached chemsketch document for its structure.
Along with the other components of the Pyrethrum extract, Pyrethrin II is used a
safe insecticide because it has a rapid knockdown effect on insects, while
maintaining low toxicity toward mammals. It is also less harmful to the
environment than many other insecticides because it has rapid biodegradability.
One might find this compound in fly sprays, household insecticides and grain
protectants. Because Pyrethrin II is unstable in sunlight and air,
research has focused more so on the synthesis of stable derivatives of this
compound. The Pyrethrin II involves the synthesis of trans-pyrethric acid
followed by the synthesis of a rethrolone (both trans-pyrethric acid and
rethrolone are the two key components of the Pyrethrin II molecule), and then
both of these are used as reactants to form Pyrethrin II can be seen.
- Dawn Bodinski
Taxol has been touted as the most promising anti-tumor agent of the twentieth
century. It was approved for use as a chemsynthetic drug in the fight
against ovarian cancer in 1994. Taxol was first discovered in nature n the
Pacific Yew tree. The problem with using this source is that in order to
harvest the taxanes from the bark the tree had to be killed. The Pacific
Yew tree is the slowest growing tree in the world. To harvest enough
taxanes to make enough Taxol for one person with cancer would require the
decimation of six two-hundred-year-old trees. Chemists have been
working on a laboratory synthesis of Taxol since the early seventies.
Three groups of chemists, as of 1996, have completely synthesized Taxol in the
laboratory. Each of the groups used a slightly different method to
synthesize Taxol many complicated rings. This synthesis however was very
important, not just to the world of chemistry and medicine, but also to the
cancer victims, who are now survivors. The complete synthesis of Taxol can
be found in the three journal articles listed below.
1. Nicolau, K.C., et al., Synthesis of Novel
Taxoids, 1994, Journal of American Chemical Society, 116,
2. Holton, R.A., et al., First Total Synthesis of Taxol. 1. Functionalization of
the B Ring, 1994, Journal of American Chemical Society, 116,
3. Danishefsky, S.J., et al., Total Synthesis of Baccatin III and Taxol, 1996,
Journal of American Chemical Society, 118 (12), pp.
Vanillin can be found in many plants, but is mainly known to be
found in Vanilla bean pods. In today's society, vanillin is used as a food
flavoring, in perfumes, as a reagent, and in preserving foods. Vanillin in
synthesized in the lab mainly by first the hydrolysis and second the oxidation
of LS (Lignosulfonates) into vanillin.
E - Vanessa Bintliff
Dr. Herbert Evans and Dr. Katharine Scott Bishop discovered vitamin E in 1922, while
experimenting on rats. The rats were first fed a diet that lacked vitamin E
completely. Those rats became infertile. After a while, wheat germ oil was
added to the rats’ diet and a remarkable thing happened. The rats became
fertile again. The doctors called this new found substance, “food factor X”
because it was necessary for the rats’ pregnancy. A few years later this
same oil based substance was isolated in the laboratory and became known as the
“antisterility” vitamin. Then in 1925, the “antisterility” vitamin
became known as Vitamin E or alpha-tocopherol. Vitamin E plays a major role in
maintaining healthy heart functions, along with healthy nerves and muscles. It
can also help build and strengthen capillary walls, and has been shown to help
heal wounds without scarring, and lower blood pressure. Since vitamin E
encourages collateral circulation in smaller blood vessels, it seems to promote
better healing with less scaring.Vitamin E helps to gradually break down blood
clots in a person’s circulatory system and also helps prevent more blood clots
Natural vitamin E, alpha- tocopherol, is derived from natural sources since it
is synthesized by plants and is found predominantly in plant oils. Leaves of
plants also contain high amounts of vitamin E. All seeds, nuts, and grains
contain alpha tocopherol. Other sources include wheat germ, soybean, cottonseed,
peanut, and eggs. Another major source of vitamin E is in the protective
covering of grains. In order for vitamin E to be preserved, extraction of the
oils from nuts and seeds must be done naturally by cold pressing.This process is
different from the heat extraction or chemical extraction that is commonly used
for food processing. A low cost approach to synthesizing vitamin E in a
laboratory is from petro-chemicals and turpentine. Although, this method
does pose a synthetic challenge from a methodological viewpoint due to the fact
that vitamin E contains saturated and chiral chains. This synthesizing
also helps produce Vitamin E in high yields and high selectivity. There
are esterified forms of vitamin E such as alpha tocopherol acetate, alpha
tocopherol succinate, and alpha tocopherol nictoinate. These forms of
vitamin E are synthetic because they made in laboratories.
Jennifer. Vitamin E: Everything You Need to Know. People’s
Medical Society: Pennsylvania, 1998; pp 1-110.