Secosteroid
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A secosteroid (Script error: No such module "IPAc-en".) is a type of steroid with a "broken" ring. The word secosteroid derives from the Latin verb secare meaning "to cut",[2]Template:Rp and 'steroid'. Secosteroids are described as a subclass of steroids under the IUPAC nomenclature.[1]Template:R/superscript[3] Some sources instead describe them as compounds derived from steroids.[4]
Types or subclasses of secosteroids are defined by the carbon atoms of the parent steroid skeleton where the ring cleavage has taken place. For example, 9,10-secosteroids are derived from cleavage of the bond between carbon atoms C9 and C10 of the steroid B-ring (similarly 5,6-secosteroids, 13,14-secosteroids, etc.).[1]Template:R/superscript
The prototypical secosteroid is cholecalciferol (vitamin D3).[5] Its IUPAC systematic is "(5Z,7E)-(3S)-9,10-secocholestra-5,7,10(19)-trien-3-ol".[1]Template:R/superscript
Some nonsteroidal estrogens, like doisynolic acid (cleaved on the D ring)[6] and allenolic acid,Script error: No such module "Unsubst". are also secosteroids or secosteroid-like compounds.
See also
References
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- ↑ a b c d
- a b c Chapters 3S-8 "Ring fission" and 3S-9 "Vitamin D group"
- ^ (esp. 3S-1.4, incl. note 4) "Steroids are compounds possessing the skeleton of cyclopenta[a]phenanthrene or a skeleton derived therefrom by one or more bond scissions or ring expansions or contractions."
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External links
- Template:Replace at the U.S. National Library of Medicine Medical Subject Headings (MeSH)