(2a,3a,5a,17b)-2,3-Epoxy-17-methylandrostan-17-ol

CAS: 968-54-7

Ref. TR-E182650

Product Information

• Name: (2a,3a,5a,17b)-2,3-Epoxy-17-methylandrostan-17-ol
• Synonyms: (1S,3aS,3bR,5aS,6aS,7aR,8aS,8bS,10aS)-1,8a,10a-Trimethylhexadecahydro-1H-cyclopenta[7,8]phenanthro[2,3-b]oxiren-1-ol

Description

Applications (2α,3α,5α,17β)-2,3-Epoxy-17-methylandrostan-17-ol is an intermediate in the synthesis of 17α-Methyl-5α-androstane-2β,3α,17β)-triol (M327240), which is a derivative of Madol (M108000, which is an anabolic steroid recently identified to be misused as a doping agent. The potency of Madol (DMT) to transactivate androgen receptor (AR) dependent reporter gene expression was two times lower as compared to dihydrotestosterone (DHT).
References Zierau, O., et al.: Planta Med., 69, 856 (2003), Takahashi, M., et al.: Endocr. J., 51, 425 (2004), Labrie, F., et al.: J. Endocrinol., 184, 427 (2005), Friedel, A., et al.: Toxicol. Lett., 164, 16 (2006),

• Brand: TRC

Chemical properties

• Molecular weight: 304.47
• Formula: C₂₀H₃₂O₂
• Color/Form: Neat
• InChI: InChI=1S/C20H32O2/c1-18-11-17-16(22-17)10-12(18)4-5-13-14(18)6-8-19(2)15(13)7-9-20(19,3)21/h12-17,21H,4-11H2,1-3H3/t12-,13+,14-,15-,16-,17+,18-,19-,20-/m0/s1
• InChI key: InChIKey=OQJKVXWRHOOEFJ-WIRWPRASSA-N
• SMILES: C[C@]12C[C@H]3O[C@H]3C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O