Testosterone phenylpropionate

Base Information

• Chemical Name: Testosterone phenylpropionate
• CAS No.: 1255-49-8
• Molecular Formula: C28H36O3
• Molecular Weight: 420.592
• European Community (EC) Number: 215-014-4
• NSC Number: 26643
• UNII: 8GN84GWX51
• DSSTox Substance ID: DTXSID5048712
• Nikkaji Number: J61.332K
• Wikipedia: Testosterone_phenylpropionate
• Wikidata: Q27088964
• ChEMBL ID: CHEMBL2356993
• Mol file: 1255-49-8.mol

Synonyms:Retandrol;testosterone 17-phenylpropionate;testosterone phenylpropionate

Chemical Property of Testosterone phenylpropionate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 5.16E-12mmHg at 25°C
• Melting Point: 116.5 °C
• Refractive Index: 1.573
• Boiling Point: 546.9 °C at 760 mmHg
• Flash Point: 233.3 °C
• PSA: 43.37000
• Density: 1.13 g/cm³
• LogP: 6.06290
• Water Solubility.: 2.25mg/L(25 oC)
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 420.26644501
• Heavy Atom Count: 31
• Complexity: 747

Purity/Quality:

99% ^*data from raw suppliers

Testosterone 17-phenylpropionate analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2OC(=O)CCC4=CC=CC=C4)CCC5=CC(=O)CCC35C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4=CC=CC=C4)CCC5=CC(=O)CC[C@]35C
• Description: Testosterone phenylpropionate (BAN; TPP) (brand name Testolent), or testosterone phenpropionate, also known as testosterone hydrocinnamate, is a synthetic anabolic-androgenic steroid (AAS) and an androgen ester – specifically, the C17β phenylpropionate ester of testosterone – which was formerly marketed in Romania. It was first synthesized in 1951 and was first described in the literature by 1953. The medication was an ingredient of several isolated AAS commercial products, but was never widely used. Testosterone phenylpropionate was also notably a component of Sustanon and Omnadren, as well as of Estandron Prolongatum, Lynandron Prolongatum, and Mixogen. TPP was previously available in Great Britain.
• Biological Functions: Testosterone phenylpropionate is a synthetic anabolic-androgenic steroid (AAS) and an androgen ester. It was first reported in the scientific literature in 1955 and was an ingredient of several isolated AAS commercial products, but was never widely used. Testosterone phenylpropionate was also notably a component of Sustanon and Omnadren.

Technology Process of Testosterone phenylpropionate

There total 15 articles about Testosterone phenylpropionate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

3-phenylpropanoic acid methyl ester (103-25-3) + testosterone (58-22-0) → testosterone 17β-phenylpropionate (1255-49-8)

Guidance literature:

With Zn₄(OCOCF₃)6O; In di-isopropyl ether; for 40h; Heating;

DOI:10.1021/jo800625v

Reference yield: 64.0%

testosterone (58-22-0) + 3-phenyl-propenal (104-55-2) → testosterone 17β-phenylpropionate (1255-49-8)

Guidance literature:

With 3-butyl-1-methylimidazolium acetate; In 1,4-dioxane; at 120 ℃; for 2h;

Reference yield: 62.8%

testosterone triphenylphosphoranylideneacetate (131447-69-3) + benzyl alcohol (100-51-6,185532-71-2) → testosterone 17β-phenylpropionate (1255-49-8)

Guidance literature:

With potassium tert-butylate; C₁₆H₃₅BrMnN₃O₂P₂; In 1,4-dioxane; at 130 ℃; for 24h; Inert atmosphere;

DOI:10.1002/adsc.202001209

upstream raw materials:

testosterone

3-phenylpropionic anhydride

hydrocinnamic acid chloride

3-Phenylpropionic acid

Downstream raw materials:

3-isopentyloxy-17β-(3-phenyl-propionyloxy)-androsta-3,5-diene

3-benzylsulfanyl-17β-(3-phenyl-propionyloxy)-androsta-3,5-diene

3-Chlor-17β-<3-phenyl-propionyloxy>-androsta-3,5-dien

Refernces

• 1、 -. "Ionic liquid catalytic synthesis of styrene-acrylic acid ester derivative of the method (by machine translation)". Paragraph 0036. . Retrieved 2019/05/08.