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Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
11-Ketodihydrotestosterone (11-KDHT; 5α-Dihydro-11-keto testosterone) is an endogenous steroid and a metabolite of 11β-Hydroxyandrostenedione. 11-Ketodihydrotestosterone is an active androgen and is also a potent androgen receptor (AR) agonist with a K i of 20.4 nM and an EC 50 of 1.35 nM for human AR . 11-Ketodihydrotestosterone drives gene regulation, protein expression and cell growth in androgen-dependent prostate cancer cells
In Vitro
11-Ketodihydrotestosterone (11-KDHT; 1-10 nM; 24 hours; LNCaP and VCaP cells) treatment induces significant cell proliferation. 11-Ketodihydrotestosterone (11-KDHT; 0.1-10 nM; 7-10 days; LNCaP and VCaP cells) treatment results in the significant upregulation of KLK3 , TMPRSS2 and FKBP5 in both LNCaP and VCaP cells, with the exception of KLK3 at 1 nM in LNCaP cells. In PNT2 cells, only 20% of 11β-hydroxyandrostenedione (11OHA4) and 11β-hydroxytestosterone (11OHT) are metabolised with the former yielding 11keto-androstenedione (11KA4), 11-Ketodihydrotestosterone (11-KDHT) and 11β-hydroxy-5α-androstanedione (11OH-5αDIONE) and the latter yielding 11OHA4, 11KT and 11-Ketodihydrotestosterone with downstream products <0.03 μM. In prostate cancer tissue, C11-oxy C19 metabolites at significantly higher levels than the C19 steroids are detected, with unconjugated 11-Ketodihydrotestosterone, 11KT and 11OHA4 levels ranging between 13 and 37.5 ng/g. Analyses of total steroid levels in plasma show significant levels of 11OHA4 (≈230-440 nM), 11KT (≈250-390 nM) and 11-Ketodihydrotestosterone (≈19 nM). MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Proliferation AssayCell Line: LNCaP and VCaP cells Concentration: 0.1 nM, 1 nM or 10 nM Incubation Time: 7 days (LNCaP cells) or 10 days (VCaP cells) Result: Induced significant cell proliferation. RT-PCRCell Line: LNCaP and VCaP cells Concentration: 1 nM, 10 nM Incubation Time: 24 hours Result: Resulted in the significant upregulation of KLK3 , TMPRSS2 and FKBP5 in both LNCaP (Fig 3) and VCaP (Fig 4) cells.
Form:Solid
IC50& Target:Ki: 20.4 nM (Human androgen receptor), EC50: 1.35 nM (Human androgen receptor)
| Canonical Smiles | CC12CCC(=O)CC1CCC3C2C(=O)CC4(C3CCC4O)C |
|---|---|
| IUPAC Name | (5S,8S,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-2,4,5,6,7,8,9,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,11-dione |
| InChIKey | RSQKILYTRHKUIJ-HZGXJFKTSA-N |
| INCHI | 1S/C19H28O3/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/h11,13-14,16-17,22H,3-10H2,1-2H3/t11-,13-,14-,16-,17+,18-,19-/m0/s1 |
| Isomeric SMILES | C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@H]4O)C |
| Alternate CAS | 32694-37-4 |
| PubChem CID | 11197479 |
| MeSH Entry Terms | 11-ketodihydrotestosterone |
| Molecular Weight | 304.42 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Steroids and steroid derivatives |
| Subclass | Androstane steroids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Androgens and derivatives |
| Alternative Parents | 3-oxo-5-alpha-steroids 17-hydroxysteroids 11-oxosteroids Secondary alcohols Cyclic ketones Cyclic alcohols and derivatives Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aliphatic homopolycyclic compounds |
| Substituents | Androgen-skeleton - 3-oxosteroid - Hydroxysteroid - 11-oxosteroid - Oxosteroid - 17-hydroxysteroid - 3-oxo-5-alpha-steroid - Cyclic alcohol - Ketone - Secondary alcohol - Cyclic ketone - Organic oxygen compound - Organooxygen compound - Alcohol - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aliphatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. |
| External Descriptors | Not available |
| Solubility | DMSO : 100 mg/mL (328.49 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 304.400 g/mol |
| XLogP3 | 2.300 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Exact Mass | 304.204 Da |
| Monoisotopic Mass | 304.204 Da |
| Topological Polar Surface Area | 54.400 Ų |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Complexity | 527.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 7 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |