Secosteroid

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[1]

IUPAC-approved carbon numbering and ring labeling is shown in the picture. Since secosteroids are derived from steroids, they retain the same labeling system as steroids. [1]
: §3S-8 
The parent steroid skeleton. The B-ring of the parent steroid is broken between C9 and C10 to yield D vitamins.

A secosteroid (

IUPAC nomenclature.[1]: §3S-1 [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]: §3S-8 

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]: §3S-8 

Some nonsteroidal estrogens, like doisynolic acid (cleaved on the D ring)[6] and allenolic acid,[citation needed] are also secosteroids or secosteroid-like compounds.

References

  1. ^
    doi:10.1351/pac198961101783
    .
    1. a b c Chapters 3S-8 "Ring fission" and 3S-9 "Vitamin D group"
    2. ^ (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."
  2. ISBN 978-0-8165-0305-6
    .
  3. ISBN 978-0-412-27060-4
    .
  4. ^ "Definition of secosteroid". Farlex Partner Medical Dictionary. TheFreeDictionary.com. A compound derived from a steroid in which there has been a ring cleavage.
  5. PMID 20424788
    .
  6. PMID 3172773
    .

External links
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