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Chapter 8: Problem 12

Describe all of the structural differences between cholesterol and stigmasterol.

Short Answer

Expert verified
The main differences between cholesterol and stigmasterol are found in their side chains and number of double bonds. Specifically, stigmasterol has an additional ethylidene group at carbons 22 and 23 and a double bond at carbons 5 and 6, both of which are absent in cholesterol.

Step by step solution

01

Understand the structure of Cholesterol

Cholesterol is a sterol with four cycloalkane rings: three six-member cyclohexane rings and a five-member cyclopentane ring. The hydrocarbon side chain is connected to the D-ring, and one hydroxyl group (-OH) is linked to the first ring, making it an alcohol.
02

Identify the structure of Stigmasterol

Stigmasterol is also a sterol with almost the same structure as cholesterol. It also contains four cycloalkane rings and a hydrocarbon side chain. However, unlike cholesterol, stigmasterol also has an ethylidene group comprised of two carbons and a double bond at C22/C23 and a double bond at C5/C6.
03

Identify the differences

Primarily, the differences between the two molecules exist in the side chains and the presence of double bonds. Unlike Cholesterol, Stigmasterol has two additional double bonds, one at carbon numbers 5 and 6 and another within the ethylidene group at carbons 22 and 23 - this group being another difference since it doesn't exist in cholesterol.

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Most popular questions from this chapter

As you read Section \(8.7,\) you might have noticed that phospholipase \(\mathrm{A}_{2},\) the enzyme found in rattlesnake venom, is also the enzyme that produces essential and beneficial lipid signals in most organisms. Explain the differing actions of phospholipase \(A_{2}\) in these processes.

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