(22S)-Budesonide

Base Information

• Chemical Name: (22S)-Budesonide
• CAS No.: 51372-28-2
• Deprecated CAS: 68678-72-8,103764-09-6
• Molecular Formula: C25H34 O6
• Molecular Weight: 430.541
• European Community (EC) Number: 257-160-1,257-139-7
• UNII: 168L5HT37P
• DSSTox Substance ID: DTXSID20860628
• Nikkaji Number: J261.701C
• Wikipedia: Budesonide
• Wikidata: Q27251792
• NCI Thesaurus Code: C80808
• Mol file: 51372-28-2.mol

Synonyms:Budesonide;Budesonide, (R)-Isomer;Budesonide, (S)-Isomer;Horacort;Pulmicort;Rhinocort;Tarpeyo

Chemical Property of (22S)-Budesonide

Chemical Property:

• Melting Point: 196-198°C
• Boiling Point: 617.9°Cat760mmHg
• PKA: 12.87±0.10(Predicted)
• Flash Point: 208.9°C
• PSA: 93.06000
• Density: 1.28g/cm³
• LogP: 2.37080
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform (Slightly), Dichloromethane, Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 430.23553880
• Heavy Atom Count: 31
• Complexity: 862

Purity/Quality:

98%Min ^*data from raw suppliers

(22S)-Budesonide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1OC2CC3C4CCC5=CC(=O)C=CC5(C4C(CC3(C2(O1)C(=O)CO)C)O)C
• Isomeric SMILES: CCC[C@H]1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@@]5([C@H]4[C@H](C[C@@]3([C@@]2(O1)C(=O)CO)C)O)C
• Recent ClinicalTrials: Budesonide Multimatrix(MMX) Versus Prednisolone in Management of Mild to Moderate Ulcerative Colitis
• Recent EU Clinical Trials: Increase in inhaled corticosteroid dose vs triple therapy in T2-high asthma patients who remain uncontrolled with medium dose inhaled corticosteroids/long-acting β2 adrenergic combination: a real-life study. TRICORDA Study (Triple vs Inhalados CORticoides a Dosis Altas).
• Uses: Budesonide (B689490) epimer S. Budesonide 22R epimer is more active than 22S epimer.

Technology Process of (22S)-Budesonide

There total 8 articles about (22S)-Budesonide 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:

desonide (13951-70-7) + butyraldehyde (123-72-8) → budesonide + (22S)-Budesonide (51372-28-2)

Guidance literature:

hydrogenchloride; In water; at 5 ℃; for 2.5h; Product distribution / selectivity;

Reference yield:

budesonide (51372-29-3) → budesonide + (22S)-Budesonide (51372-28-2)

Guidance literature:

Purification / work up; Resolution of racemate;

Reference yield:

C39H51NO9 → 3,4-dihydro-2(1H)-quinolone (553-03-7) + (22S)-Budesonide (51372-28-2)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 0 °C / Inert atmosphere

2: aq. buffer / 37 °C

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.bmcl.2012.10.006

upstream raw materials:

budesonide

desonide

butyraldehyde

2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate