Synthesis of Cinnamaldehyde
Vidallon, Mark Louis P. Date Performed: February 20, 2012 CHEM44.1 2L Date Submitted: March 12, 2012
MIXED-ALDOL CONDENSATION
Synthesis of Cinnamaldehyde
I. Introduction
Cinnamaldehyde, cinnamic aldehyde or 3-phenyl-2-propenal is the major constituent of cinnamon oil, extracted from several species of Cinnamomum (C. verum, C. burmanii, C. cassia), under the family Lauraceae, a group of evergreen trees. Cinnamon bark (particularly C. verum) yields 0.4-0.8% oil, which contains 60-80% cinnamaldehyde, 4-5% sesquiterpenoids (α-humulene, β-caryophyllene, limonene and others), eugenol, cinnamyl acetate, eugenol acetate, cinnamyl alcohol, methyl eugenol, benzaldehyde, benzyl benzoate, cuminaldehyde, monoterpenes (linalool, pinene, phellandrene and cymene), safrole and others (List and Horhammer; Masada; Ravindran qtd. from Khan and Abourashed, 2011). Isolation of cinnamaldehyde from cinnamon oil of Cinnamomum sp. bark, called “quills”, “quillings”, “featherings” and “chips” depending on quality, was first done in 1834 by Dumas and Peligot (Attokaran, 2011). It has been proven that cinnamaldehyde from cinnamon oil has a very high potential in the pharmaceutical industry, aside from its well known role in the food preparation, specifically as spice, odorant and colorant. Several researches have proven the antimicrobial activity of cinnamaldehyde against Salmonella typhimurium and Bacillus subtilis (Council of Europe, 2008). Also, cinnamaldehyde has been proven to inhibit microbial growth of opportunistic human pathogenic fungi, such as Aspergillus niger, Candida albicans and Rhizopus oligosporus, and various bacteria (Escherichia coli, Enterobacter cloacae, Micrococcus luteus, Staphylococcus aureus, Streptococcus faecalis, and others) (Khan and Abourashed, 2011). Several studies have also unraveled the hypoglycemic (insulin-like) and hypolipidemic properties of cinnamaldehyde since it can cause: elevated glucose oxidation and uptake, causing decrease in blood plasma
MIXED-ALDOL CONDENSATION
Synthesis of Cinnamaldehyde
I. Introduction
Cinnamaldehyde, cinnamic aldehyde or 3-phenyl-2-propenal is the major constituent of cinnamon oil, extracted from several species of Cinnamomum (C. verum, C. burmanii, C. cassia), under the family Lauraceae, a group of evergreen trees. Cinnamon bark (particularly C. verum) yields 0.4-0.8% oil, which contains 60-80% cinnamaldehyde, 4-5% sesquiterpenoids (α-humulene, β-caryophyllene, limonene and others), eugenol, cinnamyl acetate, eugenol acetate, cinnamyl alcohol, methyl eugenol, benzaldehyde, benzyl benzoate, cuminaldehyde, monoterpenes (linalool, pinene, phellandrene and cymene), safrole and others (List and Horhammer; Masada; Ravindran qtd. from Khan and Abourashed, 2011). Isolation of cinnamaldehyde from cinnamon oil of Cinnamomum sp. bark, called “quills”, “quillings”, “featherings” and “chips” depending on quality, was first done in 1834 by Dumas and Peligot (Attokaran, 2011). It has been proven that cinnamaldehyde from cinnamon oil has a very high potential in the pharmaceutical industry, aside from its well known role in the food preparation, specifically as spice, odorant and colorant. Several researches have proven the antimicrobial activity of cinnamaldehyde against Salmonella typhimurium and Bacillus subtilis (Council of Europe, 2008). Also, cinnamaldehyde has been proven to inhibit microbial growth of opportunistic human pathogenic fungi, such as Aspergillus niger, Candida albicans and Rhizopus oligosporus, and various bacteria (Escherichia coli, Enterobacter cloacae, Micrococcus luteus, Staphylococcus aureus, Streptococcus faecalis, and others) (Khan and Abourashed, 2011). Several studies have also unraveled the hypoglycemic (insulin-like) and hypolipidemic properties of cinnamaldehyde since it can cause: elevated glucose oxidation and uptake, causing decrease in blood plasma
References: ATTOKARAN M. 2011. Natural Food Flavors and Colorants. Germany: J. Wiley and Sons. BABU P, PRABUSEENIVASAN S and IGNACIMUTHU S. 2006. Cinnamaldehyde: A Potential Antidiabetic Agent. Phytomedicine. 1:15-22. CAREY FA and SUNDBERG RJ. 2001. Advanced Organic Chemistry Part B: Reactions and Synthesis. 4th Ed. USA: Plenum Publishers. COUNCIL OF EUROPE. 2008. Natural Sources of Flavorings. France: Council of Europe. FOX MA and WHITESELL JK. 2004. Organic Chemistry. 3rd Ed. USA: Jones and Bartlett Publishers. GHOLIVAND MB and AHMADI F. 2008. Simultaneous Determination of Trans-Cinnamaldehyde and Benzaldehyde in Different Real Samples by Differential Pulse Polarography and Study of Heat Stability of Trans-Cinnamaldehyde. Analytical Letters. 41:3324-3341. JOHNSON W. 1999. Invitation to Organic Chemistry. USA: Jones & Bartlett Learning. LISTER T and RENSHAW J. 2000. Understanding Chemistry for Advanced Level. China: Nelson Thornes. MACOMBER R. 1996. Organic Chemistry. USA: University Science Books. MAYO D, PIKE R. and FORBES, D. 2001. Microscale Organic Laboratory: With Multistep and Multiscale Syntheses. USA: John Wiley and Sons, Inc. MCFARLAND, DS. 2009. CSS: The Missing Manual. 2nd Ed. USA: O’Reilly Media Inc. MCMURRY J and SIMANEK E. 2008. Fundamentals of Organic Chemistry. 6th Ed. Singapore: Thomson Learning. MOORE JT and LANGLEY RH. 2010. Organic Chemistry II for Dummies. USA: Wiley Publishing. STOKER S. 2009. General, Organic and Biological Chemistry. USA: Cengage Learning.