11-Ketotestosterone

11-Ketotestosterone

Names
IUPAC name 17-Hydroxyandrost-4-ene-3,11-dione
Other names 11-Ketotestosterone; 11-Oxotestosterone
Identifiers
CAS Number	53187-98-7
ChemSpider	4445528
Jmol interactive 3D	Image Image
PubChem	104796
InChI InChI=1S/C19H26O3/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/h9,13-14,16-17,22H,3-8,10H2,1-2H3/t13-,14-,16-,17+,18-,19-/m0/s1 Key: WTPMRQZHJLJSBO-XQALERBDSA-N InChI=1/C19H26O3/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/h9,13-14,16-17,22H,3-8,10H2,1-2H3/t13-,14-,16-,17+,18-,19-/m0/s1 Key: WTPMRQZHJLJSBO-XQALERBDBO
SMILES CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4O)C O=C2C[C@]4([C@H]([C@@H]3CC\C1=C\C(=O)CC[C@]1(C)[C@@H]23)CC[C@@H]4O)C
Properties
Chemical formula	C19H26O3
Molar mass	302.40794
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

11-Ketotestosterone is an oxidized form of testosterone that contains a keto group at position-11. It is related to adrenosterone, an androgen found in trace quantities in humans. In fish, 11-ketotestosterone functions as the endogenous androgenic sex hormone.^[1][2] In midshipman fish, 11-ketotestosterone is not present in females or Type II Males - Type II Males reach sexual maturation later, are less territorial, and have higher testosterone than Type I Males.

References

1. Nelson, Randy F. (2005). An introduction to behavioral endocrinology. Sunderland, Mass: Sinauer Associates. p. 143. ISBN 0-87893-617-3.
2. Nagahama Y, Miura T, Kobayashi T (1994). "The onset of spermatogenesis in fish". Ciba Found. Symp. 182: 255–67; discussion 267–70. PMID 7835154.