Organic chemistry: Chamomile

Project: Functional group identification of organic compounds in herbs

Purpose: To do research on organic chemistry in chamomile, to be able to identify functional

groups of the organic compound in chamomile and to practice using ChemSketch drawing
the structure.

Chamomile:
Chamomile is well-known as one of the important medicinal herb. It has been used in
herbal remedies for thousands of years, known in ancient Egypt, Greece, and Rome. The
plants can be found also in North Africa, Asia, North and South America, Australia, and New
Zealand. Hungary is the main producer of this plant. In Hungary, chamomile is one of the
main export good to Germany for distillation of the oil. It also grown well in poor soil and be a
main income for poor people in this area. As a medicine, it is used to cure patines from
flatulence, colic, hysteria, and intermittent fever. Chamomile contains the blue essential oil
from 0.2 to 1.9%, which finds a variety of uses. Chamomile is used mainly as an
anti-inflammatory and antiseptic, also antispasmodic and mildly sudorific. It is used internally
mainly as a tisane, an herbal tea, for helping the stomach associated with pain, for sluggish
digestion, for diarrhea and nausea. Moreover, it is very effectively for inflammation of the
urinary tract and use to reduce the pain in menstruation for women. On the other hand,
externally use of the drug from chamomile in form of powder is applied to wounds slow to
heal, for skin eruptions, and infections, such as shingles and boils, also for hemorrhoids and
for inflammation of the mouth, throat, and the eyes.(Singh O, Khanam Z, Misra N, Srivastava
MK. Chamomile (Matricaria chamomilla L.))
In pharmaceutical uses, the chamomiles oil is extensively used in perfumery, cosmetics,
and aromatherapy, and in food industry. Two compounds that can found in chamomile are
Apigenin and Caffeic acid.
Apigenin: C15H10O5

Apigenin , combination of alcohol, ethers and ketone group, is an organic compond with the
formular C15H10O5 . It has yellow needles from aqueous pyridine. The melting point is around
345-350 degree celcious. It can dissolve in ethanol, pyridine, concentrated sulfuric acid and
very soluble in dilute alkalies. (National Center for Biotechnology Information. PubChem
Compound Database; CID=5280443, https://pubchem.ncbi.nlm.nih.gov/ compound/5280443
(accessed June 18, 2016)). Apigenin is a natural flavone found in a 75 variety type of fruits
and vegetables such as grapefruit, oranges, garlic, guava, celery,onions and charmomile. It
has many functions such as chemopreventive agent, antioxidant ability, antiinflammatory
activity, antitumor activities and antidepressant-like efficacy. Moreover, apigenin is one of the
flavones which help to decrease the risk of certain cancers, such as breast cancer, digestive
tract caner, and skin cancer. (Wang, X., Wang, G., & Li, X. (2016, June 1). Suppression of
rat and human androgen biosynthetic enzymes by apigenin: Possible use for the treatment
of prostate cancer. Retrieved June 16, 2016, from
http://www.sciencedirect.com/science/article/pii/S0367326X16300880)

Apigenin Chemical properties:

Apigenin is an important bioactive flavonoid compound. It is found in a variety of fruits
and vegetables such as grapefruit, oranges, garlic, guava, celery, bell pepper,cabbage and
onions. Its exhibited a strong inhibitory activity against PPO and exhibit multiple functions
such as antioxidant ability, antiinflammatory activity, antitumor activities and
antidepressant-like efficacy. Apigenin has a good potential, which can provide new insights
into the application of apigenin on actual production .When the mixtures of apigenin and
CA(caffeic acid) at different concentrations were added to PPO solution, it was found that
apigenin and CA(caffeic acid) showed a synergistic effect on the inhibition of PPO for the
majority of concentrations, except for the lowest concentrations of apigenin and CA(caffeic
acid), while apigenin and C3G showed additive and subadditive effects on the inhibition of
PPO for observation of all concentrations . These results indicated that apigenin and
CA(caffeic acid) showed a stronger synergistic effect on the inhibition of PPO than other
mixtures. Reversibility and inhibition kinetics of PPO treated with apigenin for investigating
the reversibility of apigenin-mediated inhibition and suggesting that the apigenin-induced
inhibition of PPO was reversible and a noncovalent intermolecular interaction existed
between apigenin and PPO. In conclusion, Apigenin reversibly inhibited the catalytic
activity of PPO in a mixed-type manner, and had a significant synergistic effect on inhibiting
PPO activity combined with CA(caffeic acid). The thermostability of PPO decreased after
binding with apigenin, and apigenin-treated PPO might present a more disordered structure
than the normal one.

Caffeic acid: C9H8O4

Caffeic acid has yellow crystals from concentrated aqueous solutions. Alkaline
solutions turn caffeic acid from yellow to orange. Its melting point is at 225 degree celcious.
(National Center for Biotechnology Information. PubChem Compound Database;
CID=689043, https://pubchem.ncbi.nlm.nih.gov/compound/689043 (accessed June 18,
2016)). Caffeic acid, natural aromatic compound derived from the phenyl propanoid, is
widely distributed natural phenolic compound found in honey, red wines,coffee, fruits and
vegetables. It possesses as antioxidant, antithrombogenic, anti-inflammatory, antimicrobial,
antiviral, antimutagenic and antitumor activities. (Poly(3-hydroxybutyrate)/caffeic acid
electrospun fibrous materials coated with polyelectrolyte complex and their antibacterial
activity and in vitro antitumor effect against HeLa cells
http://www.sciencedirect.com/science/article/pii/S0928493116303587)
Caffeic Acid chemical properties : Caffeic acid as a green corrosion inhibitor
for mild steel From the research of corrison scince Souza, F. D. (2008, December
24). Caffeic acid as a green corrosion inhibitor for mild steel. Corrosion Science, 51,
642-649. Caffeic acid(3-(3,4-dihydroxyphenyl)-2-propenoic acid) Caffeic Acid acts in
decreasing the available cathodic reaction area and modifying the activation energy
of the anodic reaction. A mechanism is proposed to explain the inhibitory action of
the corrosion inhibitor. green corrosion inhibitors are organic compounds that act in
adsorption on the metal surface. Caffeic acid is the phenylpropenoid most
commonly found in nature and has been demonstrated to have medicinal properties,
especially as an antioxidant agent. Its electrochemical behavior in aqueous solutions
of pH 2.08.5 has been studied as it can be deduced from its chemical structure so
caffeic acid has characteristics suitable for its application as a corrosion inhibitor.
Additionally, because it is a highly water-soluble compound, it can be used across
the whole pH range. The results obtained show that caffeic acid is a good corrosion
inhibitor for mild steel under acidic conditions. The maximum inhibition efficiency was
96%. Excellent agreement between the inhibition efficiencies calculated using
different techniques was obtained. The adsorption of the organic inhibitor onto the
steel surface was characterized by the decrease in (i) the cathodic and anodic
current densities observed in the potentiodynamic polarization curves carried out in
the presence of caffeic acid, (ii) the weight loss of the coupons immersed in the
solutions containing the inhibitor, (iii) the double-layer capacitance computed from
electrochemical impedance spectroscopy experiments. And also, the Raman
spectrum of the steel surface obtained after a polarization corrosion test proved that
the caffeic acid adsorption process took place and, partially, the shift in the OCP and
Ecorr values after addition of the caffeic acid led to the same conclusion. It acts by
blocking the cathodic surface sites and by modifying the activation energy of the
anodic reaction. In conclusion, the Raman spectrum of the steel surface supported
the mechanism proposed, in which caffeic acid undergoes chemical changes after
adsorption, but remains on the steel surface.

References:
Singh O, Khanam Z, Misra N, Srivastava MK. Chamomile (Matricaria chamomilla L.)
National Center for Biotechnology Information. PubChem Compound Database;
CID=5280443, https://pubchem.ncbi.nlm.nih.gov/ compound/5280443 (accessed June 18,
2016)
National Center for Biotechnology Information. PubChem Compound Database;
CID=689043, https://pubchem.ncbi.nlm.nih.gov/compound/689043 (accessed June 18,
2016)

Wang, X., Wang, G., & Li, X. (2016, June 1). Suppression of rat and human
androgen biosynthetic enzymes by apigenin: Possible use for the treatment of
prostate cancer. Retrieved June 16, 2016, from
http://www.sciencedirect.com/science/article/pii/S0367326X16300880

Poly(3-hydroxybutyrate)/caffeic acid electrospun fibrous materials coated with polyelectrolyte

complex and their antibacterial activity and in vitro antitumor effect against HeLa cells
http://www.sciencedirect.com/science/article/pii/S0928493116303587

Souza, F. D. (2008, December 24). Caffeic acid as a green corrosion inhibitor

for mild steel. Corrosion Science, 51, 642-649.
http://www.sciencedirect.com/science/article/pii/S0010938X08005301