Androstane

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Androstane
Names
IUPAC name
5ξ-Androstane
Systematic IUPAC name
(3aS,3bS,5aΞ,9aS,9bS,11aS)-9a,11a-Dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene
Other names
Etioallocholane; 10β,13β-Dimethylgonane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C19H32/c1-18-11-5-7-16(18)15-9-8-14-6-3-4-12-19(14,2)17(15)10-13-18/h14-17H,3-13H2,1-2H3/t14?,15-,16-,17-,18-,19-/m0/s1 checkY
    Key: QZLYKIGBANMMBK-FZFXZXLVSA-N checkY
  • C[C@@]12[C@](CCC2)([H])[C@]3([H])CCC4([H])CCCC[C@]4(C)[C@@]3([H])CC1
  • C3C1CCCC[C@@]1([C@H]2CC[C@]4([C@H]([C@@H]2C3)CCC4)C)C
Properties
C19H32
Molar mass 260.465 g·mol−1
Density 0.95 g/ml
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Androstane is a C19 steroidal hydrocarbon with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane.

  • 5α-Androstane
    5α-Androstane
  • 5β-Androstane
    5β-Androstane

Pharmacology

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5α-Androstane is reported to be effective as an androgen, in spite of having no oxygen containing functional groups.[1][2]

Androstanes

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Androstanes are steroid derivatives with carbons present at positions 1 through 19.

See also: List of androstanes


See also

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References

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  1. ^ Wilson JD (1996). "Role of dihydrotestosterone in androgen action". Prostate Suppl. 6 (S6): 88–92. doi:10.1002/(SICI)1097-0045(1996)6+<88::AID-PROS17>3.0.CO;2-N. PMID 8630237. S2CID 41352599.
  2. ^ Segaloff A, Gabbard RB (1960). "5α-Androstane—An Androgenic Hydrocarbon". Endocrinology. 67 (6): 887–889. doi:10.1210/endo-67-6-887. ISSN 0013-7227. PMID 13749674.


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