The systematic name for the given steroid is to be determined. Concept introduction: Steroids are a group of compounds that are obtained from lipids of plants and animals. Chemically, they are the derivatives of perhydrocyclopentanophenanthrene ring system. Pregnane is a 21-carbon saturated hydrocarbon steroid that is responsible for producing progestins. It is an alkane -based steroid, but group of 5 − α or β − pregnan-ol are alcohol-based steroids. Androstan are a group of steroid hormones. The 5 α − Estran − one group of steroids include hormones, such as androgen, estrogen, and progesterone. The numbering of the carbon atoms and naming of the ring system are done as shown in the figure. The A, B ring junction may be cis or trans , but B, C and C, D ring junctions are mostly trans . The methyl groups attached at the points of the ring junction are called angular methyl groups and they are the reference points for the stereochemical designations. Conventionally, groups that lie on the top of the molecule, same as that of the angular methyl group, are designated as β − groups while those at the bottom are designated as α − groups . When α and β positions are applied for hydrogen atom at C-5, and the A, B ring junction is cis , it is designated as 5 β − series and when the A, B ring junction is trans , it is designated as 5 α − series . The nature of the R − group(s) at the carbon-position determines the base name of the individual steroid.

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Chapter 23, Problem 7Q

Interpretation Introduction

Interpretation:

The systematic name for the given steroid is to be determined.

Concept introduction:

Steroids are a group of compounds that are obtained from lipids of plants and animals. Chemically, they are the derivatives of perhydrocyclopentanophenanthrene ring system.

Pregnane is a 21-carbon saturated hydrocarbon steroid that is responsible for producing progestins. It is an alkane-based steroid, but group of 5−α or β− pregnan-ol are alcohol-based steroids.

Androstan are a group of steroid hormones. The 5α−Estran−one group of steroids include hormones, such as androgen, estrogen, and progesterone.

The numbering of the carbon atoms and naming of the ring system are done as shown in the figure. The A, B ring junction may be cis or trans, but B, C and C, D ring junctions are mostly trans.

The methyl groups attached at the points of the ring junction are called angular methyl groups and they are the reference points for the stereochemical designations.

Conventionally, groups that lie on the top of the molecule, same as that of the angular methyl group, are designated as β−groups while those at the bottom are designated as α−groups. When α and β positions are applied for hydrogen atom at C-5, and the A, B ring junction is cis, it is designated as 5β−series and when the A, B ring junction is trans, it is designated as 5α−series.

The nature of the R−group(s) at the carbon-position determines the base name of the individual steroid.

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