11β-Hydroxydihydrotestosterone

11β-Hydroxydihydrotestosterone is an endogenous steroid.[1][2][3] Although it may not have significant androgenic activity, it may still be an important precursor to androgenic molecules.[3]

11β-Hydroxydihydrotestosterone
Names
IUPAC name
11β,17β-dihydroxy-5α-androstan-3-one
Systematic IUPAC name
(5S,8S,9S,10S,11S,13S,14S,17S)-11,17-dihydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
Other names
5α-androstan-11β,17β-diol-3-one
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C19H30O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h11,13-17,21-22H,3-10H2,1-2H3/t11-,13-,14-,15-,16-,17+,18-,19-/m0/s1
  • C1CC(=O)C[C@]2([H])CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)C[C@H](O)[C@]3([H])[C@@]12C
Properties
C19H30O3
Molar mass 306.446 g·mol−1
Hazards
GHS labelling:
GHS08: Health hazard
Danger
H351, H360
P201, P202, P281, P308+P313, P405, P501
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. Storbeck KH, Bloem LM, Africander D, Schloms L, Swart P, Swart AC (September 2013). "11β-Hydroxydihydrotestosterone and 11-ketodihydrotestosterone, novel C19 steroids with androgenic activity: a putative role in castration resistant prostate cancer?". Mol Cell Endocrinol. 377 (1–2): 135–46. doi:10.1016/j.mce.2013.07.006. PMID 23856005. S2CID 11740484.
  2. Van Rooyen, D.; Gent, R.; Barnard, L.; Swart, A. C. (2018). "The in vitro metabolism of 11β-hydroxyprogesterone and 11-ketoprogesterone to 11-ketodihydrotestosterone in the backdoor pathway". The Journal of Steroid Biochemistry and Molecular Biology. 178: 203–212. doi:10.1016/j.jsbmb.2017.12.014. PMID 29277707. S2CID 3700135.
  3. Masiutin M, Yadav M (2023). "Alternative androgen pathways". WikiJournal of Medicine. 10: X. doi:10.15347/WJM/2023.003. S2CID 257943362.
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