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Dehydronandrolone Acetate

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Dehydronandrolone Acetate Basic information

Product Name:
Dehydronandrolone Acetate
Synonyms:
  • 17-ACETOXYESTRA-4,6-DIEN-3-ONE
  • 17b-Acetyloxy-estra-4,6-diene-3-one
  • DEHYDRONANDROLON
  • 4,6-ESTRADIEN-17-BETA-OL-3-ONE ACETATE
  • 6-DEHYDRONANDROLONE ACETATE
  • (8R,9S,13S,14S,17S)-13-Methyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
  • Dehydronandrolone Acetate
  • Dehydronandrolone-6 Acetate
CAS:
2590-41-2
MF:
C20H26O3
MW:
314.42
EINECS:
643-000-1
Product Categories:
  • API
  • Intermediates
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Steroids
Mol File:
2590-41-2.mol
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Dehydronandrolone Acetate Chemical Properties

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)
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Dehydronandrolone Acetate Usage And Synthesis

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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