ORGANIC CHEMISTRY
1. Piperine (Pepper)
BACKGROUND
INFORMATION
A new group of alkaloid was
appeared in 1819 by the isolation
of piperine from Piperine nigrum.
[1]
They called this compound as
piperine-type alkaloids or
alkamindes or piperamides was confined from piper. Piperine is alkaloid group which has C17H19NO3 as its
molecule formula. The IUPAC name is (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta- 2,4
-dien-1-one. [6]
Piperine is an organic compound that has the average weight at 285.343 g/mol.
Chemical / physical properties
Piperine is organic compound which classed either with the lipid family or with the alkaloids. It constitute
[4]
about 5-9 percent of commercial black or white pepper. Piperine is commonly found in peppercorn,
[3]
ginger and other natural sources and is grouped as an alkaloid. Furthermore, piperine is what gives
[5]
pepper its bitter taste and it’s also responsible for making the spice an irritant, so this makes us sneeze.
The obvious example of piperine is black pepper because it is one of the well-known spices extensively used
[2]
worldwide especially in India, and Southeast Asia. The sharp odor and flavor of pepper is attributed to
[4]
the compound chavicine which is an isomer of piperine. It also used as the traditional medicine and the
insecticider. Piperine has melting point at 130 °C or 266 °F or 403 K and the boiling point is decomposed.
It is slightly soluble in water (40 mg/L, or 1g/25L (18°C)) and more so in alcohol (1g/15mL), ether
(1g/36mL) or chloroform (1g/1.7mL): the solution in alcohol has a pepper-like taste. It yields salts only with
[6]
strong acids.
2
2. Eugenol (Cloves)
BACKGROUND
INFORMATION
Eugenol is small molecule and it is a
member of the allylbenzene class of
chemical compounds which has
C10H12O2 as a molecular formula. The
IUPAC name of eugenol is
2-methoxy-4-
(prop-2-en-1-yl)phenol. It is phenylpropene, an allyl chain-substituted guaiacol. Eugenol is an organic
[7]
compound that has an average weight at 164.2011 g/mol. Also, this compound contains 4 functional
groups which consisted of aldehyde, alcohol, methoxy and allylbenzene.
Chemical / physical properties
Eugenol is a member of the allylbenzene class of chemical compounds. It is a clear to pale yellow oily liquid
[7]
extracted from certain essential oils especially. Moreover, it has a pleasant, spicy, clove-like odor.
Eugenol has medicinal value, but it is also used in products such as perfume, dentistry and clove-flavored
[9]
cigarettes. In medicine, eugenol is used as an antiseptic and an anesthetic. The example of eugenol is
basil. Its component of basil's volatile oils has been the subject of extensive study, since this substance can
[8]
block the activity of an enzyme in the body called cyclooxygenase. For the clove oil, it is made up of
between 80 to 95 percent eugenol, which is largely responsible for cloves’ ability to keep food from spoiling.
3
[10]
Eugenol has melting point at 15.4 to 15.6° F and the boiling point at 489° F. It is miscible with alcohol,
[7]
chloroform, ether, oils and it is solubility at less than 1 mg/mL.
4
Reference
[1]
Canadian Center of Science and Education. (2013). Piperine-Type Amides: Review of the Chemical and
Biological Characteristics . Retrieved from
http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.832.4635&rep=rep1&type=pdf
[2]
Namjoyan F, Hejazi H, Ramezani Z - Jundishapur J Nat Pharm Prod (2012). Chemical Structure of
Different Piperine Isomers. Retrieved from
https://openi.nlm.nih.gov/detailedresult.php?img=PMC3941875_jjnpp-07-163-e001&req=4
[3]
A.C.Kumoro, Singh H., Hasan M.(2010, January 05). Solubility of Piperine in Supercritical and Near
Critical Carbon Dioxide. Retrieved from
https://www.sciencedirect.com/science/article/pii/S1004954108603109
[4]
Britannica, T. E. (2016, April 01). Piperine. Retrieved from
https://www.britannica.com/science/piperine
[5]
TMCS. (2017). Black Pepper (Piper nigrum). Retrieved from
https://chempics.wordpress.com/2017/02/22/black-pepper-piper-nigrum/
[6]
Science of Cooking. (n.d.). Piperine -- Chemical and Physical Properties and Effects. Retrieved from
http://www.scienceofcooking.com/piperine.htm
[7]
PubChem. (n.d.). Eugenol. Retrieved from
https://pubchem.ncbi.nlm.nih.gov/compound/eugenol#section=Top
5
[8]
The world’s healthiest foods. (n.d.). Basil. Retrieved from
http://www.whfoods.com/genpage.php?tname=foodspice&dbid=85
[9]
Pavithra. B. (2014). Eugenol-A Review. Retrieved from
http://www.jpsr.pharmainfo.in/Documents/Volumes/vol6issue03/jpsr06031406.pdf
[10]
Broadhurst. L. C., James A. D., (1997). Oil of Cloves: The Benefits of Eugenol. Retrieved from
https://www.motherearthliving.com/plant-profile/eugenol
6
