Difference between revisions of "Nomenclature of steroids"

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Revision as of 17:09, 8 March 2010

The nomenclature of steroids is a subset of the nomenclature of natural products.[1]

Definitions

A steroid is a compound (either naturally occurring or artificial) based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated.[2][3] Steroids usually have methyl groups at C-10 and C-13, and often an alkyl group at C-17 (termed a "side chain"). By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.[2][3] Sterols are steroids with a hydroxyl group at C-3.[3]

Parent hydride names

Parent hydride Structure Notes
androstane
bufanolide
campestane
cardanolide Cardanolide.png configuration at C-5 must be specified for each derivative
cholane
cholestane
ergostane
estrane "estrane" is the IUPAC preferred spelling; older British texts may spell it as "oestrane"
furostan
gonane
gorgostane Gorgostane.png
poriferastane
pregnane
spirostan Spirostan.png configuration at C-5 and C-25 must be specified for each derivative
stigmastane

References

  1. Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999). Pure Appl. Chem., 71 (4), 587–643. DOI: 10.1351/pac199971040587.
  2. 2.0 2.1 steroids, <http://goldbook.iupac.org/S06005.html> (accessed 8 March 2010), Compendium of Chemical Terminology Internet edition; International Union of Pure and Applied Chemistry (IUPAC).
  3. 3.0 3.1 3.2 Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995). Pure Appl. Chem. 1995, 67 (8-9), 1307–75 at 1367. DOI: 10.1351/pac199567081307.
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