7-Keto-dehydroepiandrosterone
7-KETO DHEA · 7-Oxo-DHEA · 7-Ketoprasterone · 7-KETO DHEA, HPLC 98% · ABiraterone Impurity I · 7-Keto DHEA (Standard) · 7-keto DHEA(7-Oxo DHEA) · 7-Keto-dehydroepiandroste
Identifiers & Physical Properties
| CAS No. | 566-19-8 |
|---|---|
| Molecular formula | C19H26O3 |
| Average molar mass | 302.4 g/mol |
| Monoisotopic mass | 302.18819469 g/mol |
| SMILES | C[C@]12CC[C@H](O)CC1=CC(=O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12 |
| InChIKey | KPRGOTLNGIBVFL-GINZOMEDSA-N |
| PubChem CID | 193313 |
| ChEMBL | CHEMBL1875999 |
| ChEBI | CHEBI:183808 |
| EC No. | 111-754-6 |
| DTXSID | DTXSID801024029 |
Chemical & Physical Properties
| XLogP | 2 |
|---|---|
| Topological polar surface area | 54.4 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 0 |
| Heavy atoms | 22 |
| Formal charge | 0 |
| Complexity | 577 |
| Melting point | 245-248 °C |
| Boiling point | 477.1±45.0 °C(Predicted) |
| Density | 1.19±0.1 g/cm3(Predicted) |
| Solubility | DMF: 25 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 15 mg/mlEthanol: 10 mg/ml |
| Physical state | A crystalline solid |
| pKa (acidity coefficient) | 14.67±0.60(Predicted) |
| InChI | InChI=1/C19H26O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-14,17,20H,3-9H2,1-2H3/t12-,13-,14-,17-,18-,19-/s3 |
| InChIKey | KPRGOTLNGIBVFL-YQJRJXGQNA-N |
| SMILES | C[C@]12CC[C@H](O)CC1=CC(=O)[C@@]1([H])[C@]3([H])CCC(=O)[C@@]3(C)CC[C@]21[H] |&1:1,4,11,13,19,23,r| |
| CAS DataBase Reference | 566-19-8(CAS DataBase Reference) |
| FDA UNII | 2334LJD2E9 |
Safety & Regulations
| GHS classification | DangerH351 (100%): Suspected of causing cancer [Warning Carcinogenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Carc. 2 (100%) |
Applications & Uses
Description
7-Ketodehydroepiandrosterone (7-Keto-dehydroepiandrosterone; 7-keto-DHEA), chemically known under 3-acetyl-7-oxo-dehydroepiandrosterone, is a naturally occurring metabolite of the steroid hormone dehydroepiandrosterone (DHEA) and is marketed as such an anti-obesity dietary supplement. The synthesis of 7-keto-DHEA begins with an irreversible hydroxylation of DHEA in the position C7 by cytochrome P450 7B1 (CYP7B1) under the formation of 7 α-hydroxy-dehydroepiandrosterone (7 α-OH-DHEA). β-hydroxysteroid dehydrogenase type 1 (11 β-HSD 1) then catalyzes the interconversion of 7 α-OH-DHEA and 7 β-hydroxy-dehydroepiandrosterone (7 β-OH-DHEA) through a 7-keto-DHEA intermediary. DHEA is a "parent hormone" produced by glands near the kidneys. However, unlike DHEA, 7-keto-DHEA is not converted to steroid hormones such as androgen and estrogen. Taking 7-keto-DHEA by mouth or applying it to the skin does not increase the level of steroid hormones in the blood. People take 7-keto-DHEA for obesity, muscle strength, anxiety, depression, and other conditions. However, there is no good scientific evidence to support these uses[1].
Uses
7-Keto Dehydro Epiandrosterone-d6 is the isotope labelled analog of 7-Keto Dehydro Epiandrosterone (K187700); a metabolite of Dehydroepiandrosterone (DHEA) (D229585) which is the major secretory steroidal product of the adrenal gland.