Introduction to Natural Products
Carboxylic acids are common in nature, frequently combined with other functional groups. Simple alkyl carboxylic acids that are composed of four to ten carbon atoms are liquids or low melting solids having extremely unpleasant odors. The fatty acids are significant components of the biomolecules termed as lipids, particularly fats and oils. As displayed in the table, these long-chain carboxylic acids are generally considered to by their common names, which in most examples reflect their sources. A mnemonic phrase for C10 to C20 natural fatty acids arachidic, myristic, capric, lauric, palmitic, stearic and is: "Curly, Larry & Moe Perform Silly Antics".
Interestingly, the molecules of most natural fatty acids have an even number of carbon atoms. Analogous compounds created by odd numbers of carbon atoms are completely stable and have been made synthetically. Because nature makes these long-chain acids by linking together acetate units, it is not shocking that the carbon atoms composing the natural products are multiples of two. The double bonds inside the unsaturated compounds listed on the right are all cis (or Z).
FATTY ACIDS
Saturated
Formula
Common Name
Melting Point
CH3(CH2)10CO2H
lauric acid
45 ºC
CH3(CH2)12CO2H
myristic acid
55 ºC
CH3(CH2)14CO2H
palmitic acid
63 ºC
CH3(CH2)16CO2H
stearic acid
69 ºC
CH3(CH2)18CO2H
arachidic acid
76 ºC
Unsaturated
CH3(CH2)5CH=CH(CH2)7CO2H
palmitoleic acid
0 ºC
CH3(CH2)7CH=CH(CH2)7CO2H
oleic acid
13 ºC
CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2H
linoleic acid
-5 ºC
CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7CO2H
linolenic acid
-11 ºC
CH3(CH2)4(CH=CHCH2)4(CH2)2CO2H
arachidonic acid
-49 ºC
The following formulas are instances of other naturally occurring carboxylic acids. The molecular structures range from the simple to complex, often incorporate a range of other functional groups and several are chiral.
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