An instrument-free classification of phenolic compounds using ferric chloride reagent to improve organic chemistry teaching and learning

  • Kotchakorn Klangmanee
  • Anan Athipornchai Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Bangsaen, Chonburi 20131 Thailand
Keywords: Classification, Phenolic compounds, Ferric chloride, Organic Chemistry

Abstract

The chemistry of functional groups is an essential component of basic organic chemistry courses in the undergraduate level. A rapid qualitative method to classify the type of phenolic compounds for improves organic chemistry teaching and learning has been developed. The solution of FeCl3 was used as the reagent. The different colors of the phenolic–Fe3+ complexes solutions were observed in their phenolic compounds. The phenolic compounds with ortho-dihydroxy and ortho-trihydroxy groups specifically obtained the dark green color of the solutions. In this paper, we present a low-cost detector, designed to classify the types of phenolic compounds based on visual observation of colors, but simple enough in concept and operation to be used as a teaching tool.

References

1. Laughlin E. Organic chemistry in Ohio high schools. Journal of Chemical Education 1963;40:209–210.
2. Bell WL. Basic organic chemistry. Journal of Chemical Education 1988;65:A243.
3. Copolo CE, Hounshell PB. Using three-dimensional models to teach molecular structures in high school chemistry. Journal of Science Education and Technology 1995;4:295–305.
4. Slocum LE, Jacobsen EK. Organic chemistry in the high school curriculum. Journal of Chemical Education 2010;87:348–349.
5. Loudon M. Organic chemistry, 5th Edition. Journal of Chemical Education 2010;87:584.
6. Huang MT, Ferraro T. Phenolic compounds in food and cancer prevention, ACS Symposium Series 1992;507:8–34.
7. Balasundram N, Sundram K, Samman S. Phenolic compounds in plants and agri-industrial by-products: Antioxidant activity, occurrence, and potential uses. Food Chemistry 2006;99:191–203.
8. Leopoldini M, Russo N, Toscano M. The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chemistry 2011;125:288–306.
9. Lin D, Xiao M, Zhao J, Li Z, Xing B, Li X, et al. An overview of plant phenolic compounds and their importance in human nutrition and management of type 2 diabetes. Molecules 2016;21:1–19.
10. Monasterio RP, Olmo-García L, Bajoub A, Fernández-Gutiérrez A, Carrasco-Pancorbo A. Phenolic compounds profiling of virgin olive oils from different varieties cultivated in Mendoza, Argentina, by using liquid chromatography–mass spectrometry. Journal of Agricultural and Food Chemistry 2017;65:8184–8195.
11. Stander MA, Van Wyk BE, Taylor MJC, Long HS. Analysis of phenolic compounds in rooibos tea (Aspalathus linearis) with a comparison of flavonoid-based compounds in natural populations of plants from different regions. Journal of Agricultural and Food Chemistry 2017;65:10270–10281.
12. Li R, Narita R, Nishimura H, Marumoto S, Yamamoto SP, Ouda R, et al. Antiviral activity of phenolic derivatives in Pyroligneous acid from hardwood, softwood, and bamboo. ACS Sustainable Chemistry & Engineering 2018;6:119–126.
13. Lehmann ML, Counce RM, Counce RW, Watson JS, Labbé N, Tao J. Recovery of phenolic compounds from switch grass extract. ACS Sustainable Chemistry & Engineering 2018;6:374–379.
14. Bowsher C, Steer M, Tobin A. Plant biochemistry. Garland Science, Talor & Francis Group 2008;363–367.
15. Vermerris W, Nicholson R. Phenolic compound biochemistry. Springer Science 2008;3–30.
16. Rice-Evans CA, Miller NJ, Paganga G. Antioxidant properties of phenolic compounds. Trends in Plant Science 1997;2:152–159.
17. Cai Y, Luo Q, Sun M, Corke H. Antioxidant activity and phenolic compounds of 112 traditional Chinese medicinal plants associated with anticancer. Life Sciences 2004;74:2157–2184.
18. Moein MR, Moein S, Ahmadizadeh S. Radical scavenging and reducing power of Salvia mirzayanii subfractions. Molecules 2008;13:2804–2813.
19. Sachdev S, Davies KJA. Production, detection, and adaptive responses to free radicals in exercise. Free Radical Biology and Medicine 2008;44:215–223.
20. Bhuiyan MAR, Hoque MZ, Hossain SJ. Free radical scavenging activities of Zizyphus mauritiana. World Journal of Agricultural Sciences 2009;5:318–322.
21. Sen S, Chakraborty R, Sridhar C, Reddy YSR, De B. Free radicals, antioxidants, diseases and phytomedicine: Current status and future prospect. International Journal of Pharmaceutical Sciences Review and Research 2010;3:91–100.
22. Mimica-Dukic N, Bugarin D, Grbović S, Mitić-Ćulafić D, Vuković-Gačić B, Orčić D, et al. Essential oil of Myrtus communis L. as a potential antioxidant and antimutagenic agents. Molecules 2010;15:2759–2770.
23. Craft BD, Kerrihar AL, Amarowicz R, Pegg RB. Phenol based antioxidants and the in vitro methods used for their assessment. Comprehensive Reviews in Food Science and Food Safety 2012;11:148–173.
24. Okoh SO, Asekun OT, Familoni OB, Afolayan AJ. Antioxidant and free radical scavenging capacity of seed and shell essential oils extracted from Abrus precatorius (L.). Antioxidants 2014;3:278–287.
25. Ainsworth EA, Gillespie KM. Estimation of total phenolic content and other oxidation substrates in plant tissues using Folin-Ciocalteu reagent. Nature Protocols 2007;2:875–877.
26. Mamta S, Jyoti S. Phytochemical screening of Acorus calamus and Lantana camara. International Research Journal of Pharmacy 2012;3:324–326.
27. Dhingra S, Angrish C. Qualitative organic analysis: an efficient, safer, and economical approach to preliminary tests and functional group analysis. Journal of Chemical Education 2011;88:649–651.
28. Zohra SF, Meriem B, Samira S, Alsayadi-Muneer MS. Phytochemical screening and identification of some compounds from mallow. Journal of Natural Product and Plant Resources 2012;2:512–516.
Published
2019-12-30