3α-Etiocholanediol

3α-Etiocholanediol, or simply etiocholanediol, also known as 3α,5β-androstanediol or as etiocholane-3α,17β-diol, is a naturally occurring etiocholane (5β-androstane) steroid and an endogenous metabolite of testosterone. It is formed from 5β-dihydrotestosterone (after 5β-reduction of testosterone) and is further transformed into etiocholanolone.[1]

3α-Etiocholanediol
Names
IUPAC name
5β-Androstane-3α,17β-diol
Systematic IUPAC name
(1S,3aS,3bR,5aR,7R,9aS,9bS,11aS)-9a,11a-Dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-1,7-diol
Other names
Etiocholanediol; Etiocholane-3α,17β-diol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,17+,18+,19+/m1/s1
    Key: CBMYJHIOYJEBSB-GCXXXECGSA-N
  • C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)O
Properties
C19H32O2
Molar mass 292.463 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. PEARLMAN WH; CERCEO E (1948). "The isolation of pregnanol-3(alpha)-one-20,pregnanediol-3(alpha), 20(beta), and etiocholanediol-3(alpha),17(beta) from the bile of pregnant cows". The Journal of Biological Chemistry. 176 (2): 847–856. doi:10.1016/S0021-9258(19)52700-4. PMID 18889940.


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