Beclomethasone 17-monopropionate

Base Information

• Chemical Name: Beclomethasone 17-monopropionate
• CAS No.: 5534-18-9
• Molecular Formula: C25H33ClO6
• Molecular Weight: 464.986
• Hs Code.: 29162090
• European Community (EC) Number: 226-888-1
• UNII: 5BGA9FD55H
• DSSTox Substance ID: DTXSID20203899
• Nikkaji Number: J210.580B
• NCI Thesaurus Code: C90950
• Metabolomics Workbench ID: 154879
• ChEMBL ID: CHEMBL2115116
• Mol file: 5534-18-9.mol

Synonyms:17-BMP;beclomethasone 17-monopropionate;beclomethasone 17-propionate

Chemical Property of Beclomethasone 17-monopropionate

Chemical Property:

• Melting Point: 124-126?C
• Boiling Point: 608.9 °C at 760 mmHg
• PKA: 12.98±0.10(Predicted)
• Flash Point: 322 °C
• PSA: 100.90000
• Density: 1.3 g/cm³
• LogP: 3.12590
• Storage Temp.: -20°C Freezer
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 464.1965665
• Heavy Atom Count: 32
• Complexity: 925

Purity/Quality:

98%Min ^*data from raw suppliers

Beclomethasone17-Propionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)OC1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)Cl)O)C)C)C(=O)CO
• Isomeric SMILES: CCC(=O)O[C@@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)Cl)O)C)C)C(=O)CO
• Uses: Active metabolite of Beclomethasone Dipropionate (BDP).

Technology Process of Beclomethasone 17-monopropionate

There total 6 articles about Beclomethasone 17-monopropionate 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: 98.0%

(11β,16β)-9-chloro-17,21-[(1-ethoxypropylidene)bis(oxy)]-11-hydroxy-16-methylpregna-1,4-diene-3,20-dione, → beclomethasone 17-monopropionate (5534-18-9)

Guidance literature:

With hydrogenchloride; In methanol; water; at 25 ℃; for 3h;

DOI:10.1016/j.steroids.2021.108948

Reference yield: 88.0%

beclomethasone (4419-39-0,4647-20-5) + Triethyl orthopropionate (115-80-0) → beclomethasone 17-monopropionate (5534-18-9)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.steroids.2021.108948

Reference yield:

9β,11β-epoxy-17α,21-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0) → beclomethasone 17-monopropionate (5534-18-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / water; dichloromethane / 1.5 h / 0 - 25 °C

2: toluene-4-sulfonic acid / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

With hydrogenchloride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.steroids.2021.108948

upstream raw materials:

beclomethasone 17,21-dipropionate

beclomethasone

Triethyl orthopropionate

9β,11β-epoxy-17α,21-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione

Downstream raw materials:

beclomethasone 17,21-dipropionate

21-beclomethasone monopropionate

Refernces

• 1、 Seeto, Celina,Namkung-Matthai, Heeja,Jayram, Shalini,Kuncoro, Foe,Brown, Ken F.,Hughes, J. Margaret,Mason, Rebecca S.,Armour, Carol L.,Seale, J. Paul. "Differential potency of beclomethasone esters in-vitro on human T-lymphocyte cytokine production and osteoblast activity". . p. 417 - 423. Retrieved 2007/10/03.