Difference between revisions of "Nomenclature of steroids"
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| − | The '''nomenclature of steroids''' is a subset of the [[nomenclature of natural products]]. | + | The '''nomenclature of steroids''' is a subset of the [[nomenclature of natural products]].<ref name="NatProds">{{IUPAC natural products 1999}}.</ref> |
| + | |||
| + | ==Definitions== | ||
| + | A [[steroid]] is a compound (either naturally occurring or artificial) based on the cyclopenta[''a'']phenanthrene carbon skeleton, partially or completely hydrogenated.<ref name="GoldBook">{{GoldBookRef|title=steroids|file=S06005|accessdate=2010-03-08}}.</ref><ref name="ClassNames">{{IUPAC class names 1995|page=1367}}.</ref> 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.<ref name="GoldBook"/><ref name="ClassNames"/> [[Sterol]]s are steroids with a hydroxyl group at C-3.<ref name="ClassNames"/> | ||
==Parent hydride names== | ==Parent hydride names== | ||
Revision as of 17:53, 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 | 
|
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 | ||
| poriferastane | ||
| pregnane | ||
| spirostan | 
|
configuration at C-5 and C-25 must be specified for each derivative |
| stigmastane |
References
- ↑ Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999). Pure Appl. Chem., 71 (4), 587–643. DOI: 10.1351/pac199971040587.
- ↑ 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).
- ↑ 3.0 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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