J Forensic Sci Educ 2021, 3(1)

Extraction and Analysis of Eugenol from Cloves

James V. DeFrancesco, PhD1*

1
Loyola University Chicago, Forensic Science Program and Department of Chemistry/Biochemistry,
Flanner Hall, Rm 012, 1068 W. Sheridan Rd., Chicago, IL 60660
*corresponding author: [email protected]

Abstract: This paper describes a laboratory procedure for the extraction and identification of eugenol from
cloves (Syzygium aromaticum L.). The purpose is to instruct students in the isolation and identification of a
medicinally relevant compound from a plant via simple solvent extraction. The analytical tools employed
to identify eugenol and other naturally occurring chemical components in the cloves extract include color
tests, thin layer chromatography (TLC), infrared spectrophotometry (IR), and gas chromatography coupled
to mass spectrometry (GC-MS). In addition to eugenol, the cloves extract contains acetyl eugenol which
can be distinguished from eugenol by several test methods. Triethylamine is used as a reagent at two
different stages of testing. In the TLC analysis, triethylamine is used to basify the mobile phase which
facilitates the separation of eugenol from acetyl eugenol. The student will learn the concept of method
development by optimizing separation parameters in the TLC experiments. Additionally, the student will
learn concepts such as differential migration, interparticle forces, pKa, and surface basicity. In the GC-MS
analysis, triethylamine is used with acetic anhydride to promote the quantitative conversion of eugenol into
acetyl eugenol by removing acetic acid from the product side of the chemical equation. This provides an
opportunity for instruction of concepts such as drug derivatization, chemical equilibria, and Le Chatelier’s
principle. Several other terpenes common to plant extracts can also be identified by GC-MS. The
laboratory-based pedagogy is designed to be progressively complex to accommodate various educational
levels from high school to post-secondary.

Keywords: cloves, drug chemistry, eugenol, medicinal plants, GC-MS

Introduction

The medicinal benefits of cloves have been

recognized for thousands of years (1,2). The main
constituent, eugenol, has been used as a topical anesthetic,
adjunct component in dental applications, and recently
studied for numerous other medicinal qualities (3-10).
Traditionally, eugenol is isolated in the essential oil of
cloves which is produced via steam distillation of the
dried flowering bud of the tree Syzygium aromaticum L., FIGURE 1 Chemical structures for eugenol, acetyl
which is in the evergreen family. The analytical profile of eugenol, alpha-caryophyllene, beta-caryophyllene, and
the essential oil reveals a secondary constituent of similar caryophyllene oxide
chemical structure with purported medical benefits, acetyl
eugenol, also known as eugenol acetate (11-13), along The steam distillation method for producing the
with numerous other minor components such as terpenes, essential oil from cloves prescribed in many organic
which are common to many essential oils derived from chemistry laboratory textbooks is fairly involved and
plants (14, see Figure 1). requires specialized glassware and heating devices (15,
16). Several recent and novel alternatives to steam
distillation include use of a microwave oven (17) and an
espresso machine (18). In the same spirit of efficiency,
this new procedure employs a simple solvent extraction to
isolate eugenol followed by a multi-modal chemical
analysis. The presence of acetyl eugenol in the extract
gives the investigator an opportunity to separate and

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identify the two main components by use of TLC, FT-IR,

and GC-MS. This allows the student to learn chemical
concepts such as acid/base chemistry, pKa, derivatization,
and Le Chatelier’s principle of chemical equilibrium.
A unique feature of this experiment is the dual use of
triethylamine (TEA). In the TLC analysis, TEA is used to
basify the mobile phase and thus affect the separation of
eugenol from acetyl eugenol. In the GC-MS analysis,
TEA is used to promote the quantitative conversion of
eugenol into acetyl eugenol with acetic anhydride by
removing acetic acid from the product side of the
chemical equation (FIGURE 2-3). In the absence of FIGURE 4 Images of dried clove bud and ground cloves
TEA, the conversion of eugenol to acetyl eugenol is
incomplete. The extent of conversion is governed by Le Extraction: 0.20 to 0.60g of ground cloves (20 mesh)
Chatelier’s principle of chemical equilibrium. and 3.0 mL of IPA were placed in a 6 mL glass culture
tube and the tube was inverted several times for adequate
mixing. A clear supernatant liquid was obtained by
filtering the extract through a tightly packed cotton-plug
in a Pasteur pipet. Alternatively, a clear supernatant
liquid can be obtained by decanting the extract into a
disposable syringe and filtering through a 0.45-micron
syringe filter or via centrifugation of the extract followed
by decantation of the clear liquid. The same procedure
FIGURE 2 Partial conversion of eugenol to acetyl was followed when extracting with chloroform.
eugenol via derivatization with acetic anhydride (an Alcoholic solutions of eugenol and acetyl eugenol
equilibrium process) standards were prepared for color testing, TLC, and GC-
MS. A concentration of 100 mg/mL was used for color
However, upon addition of TEA, the conversion from testing and TLC analysis, whereas the concentration was
eugenol to acetyl eugenol proceeds rapidly and reduced to 1 to 10 mg/mL for analysis by GC-MS. The
quantitatively. This is due to the acid-base reaction of the standards are more convenient to work with in diluted
by-product of esterification, acetic acid, with TEA. form for several reasons. Color testing responses of the
pure liquids are too intense and not representative of the
lower concentrations of analytes found in most plant
extracts. Spotting of the analytes on TLC plates using
standard solutions gives a more appropriate analyte
loading than the pure liquids, which would surely
overload the capacity of the TLC plate. Likewise,
analysis by GC-MS requires analytes in a highly diluted
form to avoid overloading of the GC column. Eugenol
FIGURE 3 Quantitative conversion of eugenol to acetyl and acetyl eugenol standards were purchased from TCI
eugenol via derivatization with acetic anhydride and Chemicals.
triethylamine TLC: Flexible, plastic-backed TLC plates were
purchased from EMD Millipore (20 x 20 cm, silica gel,
200 mcm thickness, 60-angstrom pore size, F254). Spots
Methods were visualized under a 254 nm UV light. Plates are also
available with a thin aluminum backing. These flexible
Materials: Cloves were purchased from a local plates are convenient for teaching and research purposes
supermarket as the dried flowering bud and ground to a due to their ability to be cut to any size with a sharp
20-mesh powder with a coffee bean grinder to maximize scissors, or preferably a paper trimmer, and stored in a
surface area and increase extraction efficiency (FIGURE laboratory notebook. The analyte solutions were spotted
4). Isopropanol, ethyl acetate, hexane, and chloroform with micropipettes that were prepared by heating and
were purchased from EMD Millipore. stretching glass capillary tubes on a Bunsen burner and
cutting each to a useful length. The smaller diameter of
micropipettes allows for a controlled loading of solution
onto the TLC plate, which produces small, concentrated
spots at the origin. This is important since longitudinal

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diffusion causes spots to enlarge as they travel up the purchased from BDH. Dichloromethane can be
TLC plate via capillary action in the mobile phase. substituted for chloroform.
Color Test Reagents: Color test reagents were
prepared from sulfuric acid, formaldehyde, selenious acid, Hazards and Safety Precautions
and ferric chloride, all purchased from Fisher Chemicals.
Marquis reagent was prepared by mixing 10 mL of Several of the color test reagents contain strong acids,
formaldehyde (40% by volume) in 90 mL of concentrated hence appropriate personal protective equipment is
sulfuric acid (19). Mecke reagent was prepared by mixing required. All organic solvents and reagents should be
1 g of selenious acid in 100 mL of concentrated sulfuric handled in a fume hood. These materials should be
acid (20). Ferric Chloride reagent was prepared by stored, used, and disposed of in an appropriate manner.
mixing 10 g of anhydrous ferric chloride (which can be
substituted with 16.5 g of the hexahydrate) in 100 mL of Results
DI water (19). Alternatively, color test reagents can be
purchased as kits. Color testing was performed by Color Tests: The observed color changes of the
placing a few drops of the test reagent into a white alcoholic cloves extract, eugenol, and acetyl eugenol
porcelain test well, followed by addition of one drop of solutions are noted in TABLE 1. Marquis and Mecke are
sample solution into the well. In this order of addition, reagents in the “sulfuric acid series” of color tests. In the
placing the test reagent in the well first is important to Marquis test, all three turned a red color. In the Mecke test,
ensure that an initial negative response is obtained prior to all three turned an initial and brief green that immediately
addition of the sample, which indicates an turned to black. It is not surprising that the three samples
uncontaminated well. The practice serves as a negative respond similarly in the sulfuric acid tests. The strongly
control for the experiment. Chemical supplies can be acidic conditions unmask reactive groups to give a
sourced from various vendors; however, it should be common and responsive product that contains a substituted
noted that analytical grade items produce the best results. catechol moiety. A similar effect is seen in the ecstasy
IR: Infrared spectra were acquired on a Perkin-Elmer family of drugs in which the unmasking of a 3,4-
Spectrum 100 series Fourier Transform Infrared methylenedioxy group produces a catechol. The Ferric
Spectrophotometer fitted with a Universal Attenuated Chloride test proved to be more discriminating. In the
Total Reflectance Sampling accessory containing a ZnSe Ferric Chloride test, the cloves extract and eugenol
crystal. Spectra were recorded in % transmittance and standard turned light green, whereas acetyl eugenol
scanned from 4000 to 650 cm-1 for four scans per standard showed no response. The positive response for
spectrum at a resolution of 2 cm-1. Spectra of eugenol and the cloves extract was due to the presence of eugenol. This
acetyl eugenol standards were obtained neat, whereas the ability of Ferric Chloride to distinguish a phenol from an
spectrum for the alcoholic cloves extract was obtained for aryl ether or ester is found in the opiate class of drugs,
the residue by placing several drops of the extract onto the namely in the differentiation of morphine from heroin.
ATR window and allowing the solvent to evaporate. Morphine and heroin are indistinguishable in any of the
GC-MS: Total ion chromatograms and mass spectra sulfuric acid series of tests. However, in the Ferric
were obtained on an Agilent 7890A/5975C fitted with a Chloride test, morphine responds with a color change
HP-5 column (30 m long x 0.320 mm diameter x 0.250 (blue), whereas heroin has no response. In both the
mcm film thickness), a helium carrier gas flow of 1.3 eugenol/acetyl eugenol and morphine/heroin examples,
mL/min (constant flow mode), inlet temperature of 275 Ferric Chloride is a more discriminating test due to the
deg C, MS transfer line temperature of 280 deg C, oven milder chemical conditions.
program of 60-320 deg C at a 30 deg/min ramp with a 2
minute hold and solvent delay at 60 deg C and a 3 minute TABLE 1 Color test results for alcoholic cloves extract,
hold at 320 deg C. The inlet split was 50:1. The eugenol, and acetyl eugenol
quadrupole was set to scan 40-550 Daltons. The MS
source temperature was 230 deg C and the MS Sample Marquis Mecke FeCl3
quadrupole temperature was 150 deg C. Cloves extract red green to black light green
Derivatization: 0.20 mg of ground cloves was
extracted with 4.0 mL of chloroform and filtered as Eugenol red green to black light green
described earlier. The derivation was conducted in two
stages. First, 1-2 drops of acetic anhydride was added to
Acetyl eugenol red green to black NR
each of two - 1 mL aliquots of the extract. Next, 1-2
drops of triethylamine was added to only one aliquot to TLC: The TLC results show an increasing, yet
facilitate quantitative conversion of eugenol into acetyl identical response factor (Rf) for the single spot observed in
eugenol. Acetic anhydride and triethylamine were the three samples (cloves extract, eugenol, and acetyl
purchased from Aldrich Chemicals and chloroform was

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eugenol) as the proportion of ethyl acetate in the mobile IR: IR spectra of the alcoholic cloves extract residue
phase is increased. and neat standards of eugenol and acetyl eugenol are
displayed in FIGURE 6. The cloves residue appears to be
Rf = distance traveled by spot/ an additive spectrum of the two main components, eugenol
distance traveled by mobile phase (1) and acetyl eugenol. This confirms the TLC result that the
alcoholic cloves extract contains mainly eugenol and acetyl
However, when the mobile phase was modified with eugenol, from an IR spectroscopic perspective. The most
10% triethylamine (by volume), two spots were resolved distinguishing feature in the spectrum of the extract is the
from the cloves extract. A comparison of the Rf values of band at 1766 cm-1, which corresponds to the acetate ester
the spots indicates a positive identification of eugenol and moiety in acetyl eugenol (absent in eugenol). It should be
acetyl eugenol as components in the cloves extract noted that there is a slight red shift for this carbonyl band of
(FIGURE 5 and TABLE 2). Further confirmation of the about four wavenumbers in the extract compared to the
component identifications was performed by combining acetyl eugenol standard (1762 cm-1 in acetyl eugenol). This
TLC separation with color testing. This was done by is most likely due to some hydrogen bonding from eugenol
dropping a small amount of color test reagent onto the present in the extract. In controlled testing, this assertion
resolved spots of the TLC plate and observing the color was confirmed by observing a similar three-wavenumber
change. red shift of the band in a series of binary eugenol/acetyl
eugenol mixtures from zero to 100 % by weight
(unpublished results from a separate manuscript in
preparation).

FIGURE 6 IR Spectra of cloves extract (residue), acetyl

eugenol, and eugenol
FIGURE 5 TLC plates developed with hexane, ethyl
acetate, and trimethylamine (Ext = alcoholic cloves
GC-MS: A total ion chromatogram of the alcoholic
extract, Eug = eugenol, AcE = acetyl eugenol).
cloves extract is shown in FIGURE 7 and mass spectra are
shown in FIGURE 8-12. All five of the main chemical
It is interesting to note that throughout the TLC
components are resolved on a HP-5 phase column. Similar
experiment, lighter intensity spots that appear at lower Rf
chromatographic results were obtained on a lower polarity
values in the cloves extract give color test responses that do
HP-1 column (unpublished results, not shown).
not match the standards. (Caution: TLC plates exposed to
corrosive agents such as strong acids should be discarded in
a responsible manner following a color change observation
and not stored in a laboratory notebook.)

TABLE 2 Rf values for cloves extract, eugenol, and acetyl

eugenol in various TLC systems containing hexane, ethyl
acetate, and triethylamine measured as volume ratios.
Hexane/Ethyl Acetate (v/v) TEA/Ethyl Acetate (v/v)
(80/20) (50/50) (10/90) (0/100) (10/90)
Cloves extract 0.32 0.58 0.66 0.64 0.58, 0.67
Eugenol 0.32 0.58 0.66 0.64 0.58 FIGURE 7 GC-MS total ion chromatogram of
alcohol extract on HP-5 phase column
Acetyl eugenol 0.32 0.58 0.66 0.64 0.67

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A b und a nce

A v e r a g e o f 6 .6 8 6 to 6 .6 9 7 m i n .: j v d 0 3 1 2 1 9 0 0 3 .D \ d a ta .m s
1 6 4 .1
1500000 A b und a nc e

1400000

A v e ra g e o f 6.453 to 6.458 m in.: jv d 031219003.D \d a ta .m s

1300000 93.1
55000
1200000

1100000 50000

1000000
45000
900000

40000
800000

700000 35000

600000
30000
500000

25000
400000 1 4 9 .1

300000
9 1 .1 1 3 1 .1 20000 80.1
121.1
4 3 .1
200000 7 7 .1 1 0 4 .1
15000
2 0 6 .1
100000 147.1
6 3 .1
1 1 7 .1
41.2 107.1
0
1 7 7 .1 1 9 1 .3 10000 67.2
40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200
m / z -->
53.1

FIGURE 8 Mass spectrum of eugenol in alcohol extract 5000 204.2

133.1 161.2 189.2
(RT=5.972 min) 175.2
0
40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200
Abundance m /z-->

Average of 5.963 to 5.975 min.: jvd031219003.D\data.ms FIGURE 10 Mass spectrum of beta-caryophyllene in

1800000
164.1 alcohol extract (RT = 6.306 min)

1600000 A b und a nce

1400000 A ve ra g e o f 7.012 to 7.012 m in.: jvd 031219003.D \d a ta .m s

7500 79.1

1200000 7000 41.2

6500 93.1
1000000
6000
800000
5500
149.1
600000 77.1 103.1 5000
91.1 131.1
4500
400000
121.1 107.1
4000 55.1
55.1
65.1
200000
3500
41.2
0 3000
121.1
40 50 60 70 80 90 100 110 120 130 140 150 160
2500
m/z-->
2000

1500 135.1 149.1

FIGURE 9 Mass spectrum of acetyl eugenol in alcohol
extract (RT = 6.696 min) 1000
164.1
177.1

500 191.1 205.1

220.1
0
40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 210
m /z-->

FIGURE 11 Mass spectrum of alpha-caryophyllene in

alcohol extract (RT = 6.457 min)

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impact on the ratio. After only 16 hours, the conversion of

eugenol to acetyl eugenol was nearly complete.
A b und a nce

Abundance
A v e r a g e o f 6 .3 0 1 to 6 .3 0 7 m i n .: j v d 0 3 1 2 1 9 0 0 3 .D \ d a ta .m s
9 3 .1
1 3 3 .1 T IC : G L G 0 3 1 2 1 9 0 0 3 .D \ d a ta .m s
180000 6 .8 9 4

170000
6500000
Eugenol (coeluted with
6000000
Acetyl eugenol
160000
7 9 .1 alpha-Caryophyllene)
4 1 .2
150000 5500000 7 .7 3 1

140000
5000000
130000

1 0 5 .1 4500000
120000

110000
4000000

100000
3500000
90000
1 2 0 .1
3000000
80000
beta-Caryophyllene
70000 1 6 1 .2
2500000
5 5 .2 6 .6 8 3
60000 1 4 7 .1
2000000
50000

1 8 9 .2
40000 1500000

30000
1000000
1 7 5 .2
20000
2 0 4 .2 Caryophyllene oxide
500000
10000

0
40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 6 .2 0 6 .4 0 6 .6 0 6 .8 0 7 .0 0 7 .2 0 7 .4 0 7 .6 0 7 .8 0
m /z --> T im e - - >

FIGURE 13 GC-MS total ion chromatogram of alcoholic

FIGURE 12 Mass spectrum of caryophyllene oxide in extract on HP-17 phase column
alcohol extract (RT = 7.012 min).

However, when the analysis was conducted on a more

polar HP-17 column, resolution of the five components
degraded (FIGURE 13). Caryophyllene oxide was only
marginally resolved as a shoulder on the acetyl eugenol
peak and alpha-caryophyllene disappeared completely.
Upon closer inspection of the eugenol peak purity, several
fragments appeared that belong to alpha-caryophyllene and
not eugenol, namely m/z 93, 147, and 204. Subsequent
testing of the extract by evaporation of the solvent followed
by re-extraction of the resulting residue with hexane, then
back washing of the hexane solution with several volumes
of 1N NaOH to remove eugenol revealed a pure mass
spectrum for alpha-caryophyllene at the same retention
time as eugenol. Obviously, the preferred GC column
phases for this analysis are HP-1 and HP-5 (0% and 5%
phenyl, respectively), whereas the HP-17 column phase
(50% phenyl) is too polar.
The effect of adding acetic anhydride to a chloroform
FIGURE 14 Peak area ratios of eugenol to acetyl eugenol
extract of cloves over a 24-hour period is shown in
for chloroform extract + acetic anhydride and chloroform
FIGURE 14. In the absence of triethylamine, the peak
extract + acetic anhydride + triethylamine, over 134 hours
ratio of eugenol/acetyl eugenol remains nearly unchanged.
An extended time analysis showed moderate, but steady
Discussion and Conclusion
decline of this ratio after several days. This is indicative of
The experimental design described in this work
the unfavorable kinetics of this conversion in the presence
provides an effective means to extract drug components
of only acetic anhydride. However, the addition of
from plant material followed by a chemical analysis that
triethylamine to the mixture has an immediate and drastic
uses a progressively advancing series of analytical
techniques. Basic tests such as color testing and TLC

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allow for the experiment to be meaningful to modestly these experiments support the mechanism by which a base
resourced laboratories, whereas more advanced such as triethylamine or pyridine accelerates the
techniques such as IR and GC-MS are appropriate for the conversion of eugenol to acetyl eugenol by removing
college undergraduate and graduate levels. acetic acid from the product side of the equilibrium. Of
The order in which the techniques are employed course, the fact that both triethylamine and pyridine are
follows a pedagogy that dovetails various chemical tertiary bases is no coincidence. If a secondary or
concepts with analytical concepts. The use of primary amine is used in place of a tertiary amine, the rate
triethylamine in the TLC analysis causes eugenol to and extent of acetylation would be diminished due to the
separate from acetyl eugenol to the extent that each can be reactivity of these amines with acetic anhydride to form
identified based on the Rf values (TABLE 2). The amides. Amide formation will out compete esterification
mechanism by which triethylamine affects separation is from both a thermodynamic and kinetic perspective.
unclear. It is either by an increase in solvent polarity or
by introduction of an acid-base interaction. The solvent TABLE 3 pKa values for acetic acid, pyridine, eugenol,
polarity effect can be ruled out by replacing triethylamine and triethylamine
with an even more polar solvent such as isopropanol. In a
TLC experiment using a mobile phase of 10/90 Acid Base pKa
isopropanol to ethyl acetate by volume, there is no Acetic acid Acetate (anion) 4.76
separation of eugenol from acetyl eugenol in the cloves
+
extract (Rf of 0.74 for both, unpublished results). As for Pyridine-H Pyridine base 5.25
the acid-base interaction, it can occur in several ways.
Triethylamine can cause deprotonation of eugenol to form Eugenol Eugenol (anion) 10.00
the phenoxide which bears a full negative charge and thus Triethylamine-H+ Triethylamine base 10.77
has a significantly stronger interaction with the siloxy
sites on the silica gel surface than the phenol (eugenol) or
the acetate ester (acetyl eugenol). It is also possible that
triethylamine creates a more basic silica gel surface,
which in turn creates a stronger interaction with the acidic
phenol than the neutral acetate ester. The literature pKa
values of eugenol and triethylamine (actually, the
ammonium salt of triethylamine) are 10.00 and 10.77
(21), respectively (TABLE 3). This slight difference of
0.77 pKa units is enough to support a mechanism by
which the majority of eugenol is deprotonated in the
presence of triethylamine base.
The use of triethylamine in the GC analysis, in
combination with acetic anhydride, causes a rapid
conversion of eugenol to acetyl eugenol. The mechanism
of this accelerated conversion can occur in two ways:
either by removal of acetic acid from the product side of
the acetylation reaction, thus tilting the equilibrium in
favor of product formation in a classic Le Chatelier
manner or by deprotonating eugenol to form eugenol
phenoxide which is a more powerful nucleophile for
attacking the electrophilic acetic anhydride. FIGURE 15 Peak area ratios of eugenol to acetyl
Triethylamine is a sufficiently strong base to produce the eugenol for chloroform extract + acetic anhydride and
eugenol phenoxide and can act as a proton sponge for chloroform extract + acetic anhydride + pyridine, over
acetic acid. Controlled testing of the cloves extract with a 94 hours
base that is too weak to deprotonate eugenol, but strong
enough to react with acetic acid, should resolve the issue. Compared to prior methods of producing essential oil of
In fact, when triethylamine is replaced with pyridine (pKa cloves via steam distillation, this new experiment presents
of pyridine HCl = 5.25) in a chloroform extract of cloves a simpler extraction method that takes a more expansive
in the presence of acetic anhydride, the same accelerated approach to the chemical analysis. The experiment
conversion of eugenol to acetyl eugenol is observed exploits the unique combination of chemical components
(TABLE 3, FIGURE 15). If the mechanism proceeded in the extract to investigate chemical concepts of acidity,
via deprotonation of eugenol, pyridine should have no functional group transformation, and chemical kinetics.
effect on the velocity of the acetylation reaction. Thus, The analytical testing scheme provides a comprehensive

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and orthogonal analysis of the main chemical components observed in the chromatographic process
components. The analytical methods used are produces a selective bias of the distance traveled of one
appropriately selective and specific to distinguish eugenol compound compared to another that is based on the
from acetyl eugenol. Furthermore, the progressive strength of interparticle forces. The progression from
experimental design presents an opportunity for TLC to GC teaches the student that analyte selectivity can
collaboration between secondary, post-secondary, and be enhanced by increasing the number of theoretical
postgraduate institutions. Despite the comprehensive plates. The progression from a color test response to a
scope of testing, the analytical approach is focused mainly mass spectrum or IR spectrum teaches the student how
on qualitative analysis. Future work will focus on analyte specificity can be increased. That is, spectral data
quantitative analysis of the chemical components contain far more information about a certain chemical
identified in this work by chromatographic and structure than a color test response. The progression of
spectroscopic means. testing can be easily connected to the testing categories
set forth in the SWGDRUG guidelines which are grouped
Student Learning Outcomes by the level of selectivity (22).

The analysis of chemical components in plants is Acknowledgements

fundamental to the field of forensic drug analysis. The
list of controlled substances at the federal and state levels The author would like to thank the many students in
is replete with examples of drugs that are directly or drug chemistry and forensic toxicology at Loyola
indirectly derived from plants. The most widely abused University Chicago throughout the years who indulged
drug in all of human history, ethanol, is the result of the this interest in analyzing medicinal plants. The structure
action of microflora on macroflora, namely yeast on grain of these experiments was refines over numerous iterations
or other vegetative organic matter. Therefore, regardless in various laboratory sections.
of the legal status of an organic compound, chemical
analysis is chemical analysis. References
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