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CinnAcidEssay61F08
Course: ORGCHEM 61, Fall 2008School: Colorado
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edition Online for students of organic chemistry lab courses at the University of Colorado, Boulder, Dept of Chem and Biochem. (2008) Experiment 15 u Supplement forAcid Essay: Cinnamic You will note the characteristic odor of cinnamic acid as you weigh it out in preparation to the addition of bromine in the following experiment. Cinnamic acid has a spicy cinnamon odor. Actually, it is its close relative,...
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edition Online for students of organic chemistry lab courses at the University of Colorado, Boulder, Dept of Chem and Biochem. (2008)
Experiment 15 u Supplement forAcid Essay: Cinnamic
You will note the characteristic odor of cinnamic acid as you weigh it out in preparation to the addition of bromine in the following experiment. Cinnamic acid has a spicy cinnamon odor. Actually, it is its close relative, cinnamaldehyde, that is the major component of cinnamon oil, used both as a food avoring and in perfumes. Both cinnamic acid and cinnamaldehyde can be isolated from natural sources.
O H C C H Cinnamic Acid O H C C CH C OH
Cinnamon oil is an example of an essential oil; essential H oils are volatile oils derived from plants. Essential in this Cinnamaldehyde context derives from the word essence, or fragrance. These volatile oils are complex mixtures of organic molecules: esters, hydrocarbons, alcohols, and carbonyl compounds. You will become familiar with the aromas of several esters in the second semester of organic chemistry lab. The structures of many other components of essential oils fall into one of two categories, terpenes or phenylpropanoids. Terpenes are distinguished from other natural products in that each is made up of ve carbon isoprene units, as in the illustration of isoprene at the left (exclusive of its double bonds). Terpenes, often referred to as isoprenoid compounds, are classied according to the Isoprene number of carbon atoms that they contain: 10 carbons is a monoterpene, 15 is a sesquiterpene, 20 is a diterpene, 25 is a sesterpene, 30 is a triterpene, and 40 is a tetraterpene.* Examples of some common terpenes are given below. You will recognize these compounds as familiar odors or avors.
CHO OH
Limonene (citrus) Menthol (mint) Citral (lemongrass) Camphor (camphor)
O
O CH2OH
1,8-Cineole (eucalyptus) Farnesol (lily of the valley)
* See Organic Chemistry by Francis Carey, p. 1079. Essay: Cinnamic Acid 77
Online edition students for of organic chemistry lab courses at the University of Colorado, Boulder, Dept of Chem and Biochem. (2008)
Phenylpropanoids are aromatic compounds based on a phenylpropane skeleton, namely, an aromatic ring with a 3-carbon substituent. Caffeic acid and eugenol are examples of phenylpropanoids.
CO2H HO OH
Phenylpropane Caffeic acid (coffee)
HO OCH3
Eugenol (cloves)
Cinnamic acid is interesting because of its role in the synthesis of another very large class of natural products: the avonoids. Flavonoids contain fteen carbons in their basic nucleus. These carbons are arranged in a C6C3C6 conguration: two aromatic rings linked by a three carbon unit. All avonoids are related by a common biosynthetic pathway, called the shikimatic acid pathway, in which cinnamic acid is an intermediate. There are perhaps thousands of naturally occurring avonoids, all variants on the basic avonoid nucleus, some examples of which are given below. These variants are produced in plants by modication of the aromatic rings, dimerization to produce biavonoids, and glycosylation to form avonoid glycosides.
O
O flavonoid nucleus
The avonoids play a myriad of useful roles in pl...
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