| Identification | Back Directory | [Name]
11-KETOTESTOSTERONE | [CAS]
564-35-2 | [Synonyms]
Ketotestosterone
11-Oxotestosterone
11-KETOTESTOSTERONE
4-Androsten-17B-ol-3,11-dione
4-Androsten-17β-ol-3,11-dione
4-ANDROSTEN-17BETA-OL-3,11-DIONE
17β-hydroxy-4-androstene-3,11-dione
11-ketotestosterone--dea schedule iii
17BETA-HYDROXY-4-ANDROSTENE-3,11-DIONE
Androst-4-ene-3,11-dione,17-hydroxy-, (17b)-
Androst-4-ene-3,11-dione, 17-hydroxy-, (17beta)-
17β-Hydroxy-4-androstene-3,11-dione, 17β-Hydroxyandrost-4-ene-3,11-dione, 4-Androsten-17β-ol-3,11-dione
(8S,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione | [Molecular Formula]
C19H26O3 | [MDL Number]
MFCD00010469 | [MOL File]
564-35-2.mol | [Molecular Weight]
302.41 |
| Chemical Properties | Back Directory | [Melting point ]
183-184 °C(Solv: acetone (67-64-1); hexane (110-54-3)) | [Boiling point ]
476.8±45.0 °C(Predicted) | [density ]
1.19±0.1 g/cm3(Predicted) | [storage temp. ]
room temp | [solubility ]
ethanol: 9.80-10.20mg/mL, clear, colorless to faintly yellow | [form ]
Solid | [pka]
14.79±0.60(Predicted) | [color ]
White to off-white | [biological source]
synthetic (organic) | [InChI]
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-/s3 | [InChIKey]
WTPMRQZHJLJSBO-XQALERBDSA-N | [SMILES]
C[C@]12CCC(=O)C=C1CC[C@@]1([H])[C@]3([H])CC[C@H](O)[C@@]3(C)CC(=O)[C@]21[H] |&1:1,10,12,16,18,23,r| | [EPA Substance Registry System]
Androst-4-ene-3,11-dione, 17-hydroxy-, (17.beta.)- (564-35-2) |
| Hazard Information | Back Directory | [Uses]
A metabolite of Adrenosterone. | [Description]
11-keto Testosterone (CRM) (Item No. 9002654) is a certified reference material that is structurally categorized as an androgen. It is a significant hormone in certain fish, regulating the development of sexual development and behavior.1,2 11-keto Testosterone binds the stickleback kidney androgen receptor (EC50 = 43 nM).3 11-keto Testosterone, at 10 nM, significantly activates the human androgen receptor expressed in zebrafish liver cells.3 This product is intended for research and forensic applications. | [Definition]
ChEBI: 11-oxotestosterone is a 3-oxo Delta(4)-steroid that is testosterone carrying an additional oxo substituent at position 11. It has a role as an androgen, a marine xenobiotic metabolite and a human metabolite. It is a 3-oxo-Delta(4) steroid, an 11-oxo steroid, an androstanoid and a 17beta-hydroxy steroid. It is functionally related to a testosterone. It derives from a hydride of an androstane. | [Biochem/physiol Actions]
11-Ketotestosterone is a minor androgen in humans, but a major androgen in fish. | [in vivo]
In previtellogenic cultured sterlet (Acipenser ruthenus), silastic strips embedded with 11-Ketotestosterone (5 or 25 mg/kg) are implanted in vivo for 30 days. Ovarian masculinization or sex reversal is not observed. 11-Ketotestosterone promotes sterlet ovarian development in a dose-dependent manner[1]. | [References]
[1] TAKAFUMI YAMAGUCHI Masahiro S Hironobu Watanuki. Effects of estradiol, progesterone and testosterone on the function of carp, Cyprinus carpio, phagocytes in vitro[J]. Comparative Biochemistry and Physiology C-toxicology & Pharmacology, 2001, 129 1: Pages 49-55. DOI: 10.1016/s1532-0456(01)00176-4
[2] GODWIN J. Neuroendocrinology of sexual plasticity in teleost fishes[J]. Frontiers in Neuroendocrinology, 2010, 31 2: Pages 203-216. DOI: 10.1016/j.yfrne.2010.02.002
[3] PER-ERIK OLSSON. Molecular cloning and characterization of a nuclear androgen receptor activated by 11-ketotestosterone.[J]. Reproductive Biology and Endocrinology, 2005, 3: 37. DOI: 10.1186/1477-7827-3-37 |
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