| Identification | More | [Name]
Dehydronandrolon | [CAS]
2590-41-2 | [Synonyms]
17-ACETOXYESTRA-4,6-DIEN-3-ONE
17b-Acetyloxy-estra-4,6-diene-3-one
4,6-ESTRADIEN-17-BETA-OL-3-ONE ACETATE
6-DEHYDRONANDROLONE ACETATE
DEHYDRONANDROLON | [EINECS(EC#)]
643-000-1 | [Molecular Formula]
C20H26O3 | [MDL Number]
MFCD00271529 | [Molecular Weight]
314.42 | [MOL File]
2590-41-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
95-98?C | [Boiling point ]
457.4±45.0 °C(Predicted) | [density ]
1.15±0.1 g/cm3(Predicted) | [storage temp. ]
Controlled Substance, -20°C Freezer | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [color ]
Off-White to Pale Yellow | [InChI]
InChI=1/C20H26O3/c1-12(21)23-19-8-7-18-17-5-3-13-11-14(22)4-6-15(13)16(17)9-10-20(18,19)2/h3,5,11,15-19H,4,6-10H2,1-2H3/t15-,16+,17+,18-,19-,20-/s3 | [InChIKey]
OGUASZAAVFYYIL-SBVYDUMINA-N | [SMILES]
[C@@]12([H])CC[C@H](OC(=O)C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3C=C[C@@]21[H] |&1:0,4,9,13,15,25,r| | [CAS DataBase Reference]
2590-41-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Dehydronandrolone acetate is a critical precursor in the synthesis of C7-functionalized steroidal drugs such as the new anti-breast cancer drug Fulvestrant, the treatment of menopause and postmenopausal syndrome drug Tibolone, as well as the highly effective protein anabolic hormone Mibolone. Nandrolone as starting material was first subjected to simultaneous acylation with acetic anhydride and acetyl chloride to form the intermediate, which was then brominated with N-bromosuccinimide (NBS) under basic conditions to eliminate one molecule of HBr to produce Dehydronandrolone acetate (73% yield)[1].
| [Chemical Properties]
Pale Yellow Solid | [Uses]
Tibolone intermediate. | [References]
[1] Zili Zhang and Aitao Li*. “A Designed Chemoenzymatic Route for Efficient Synthesis of 6-Dehydronandrolone Acetate: A Key Precursor in the Synthesis of C7-Functionalized Steroidal Drugs.” ACS Catalysis 13 19 (2023): 13111–13116.
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