(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic acid

Base Information

• Chemical Name: (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic acid
• CAS No.: 28416-82-2
• Molecular Formula: C21H26 F2 O5
• Molecular Weight: 396.431
• Hs Code.: 2937220000
• European Community (EC) Number: 608-206-8
• DSSTox Substance ID: DTXSID201113202
• Mol file: 28416-82-2.mol

Synonyms:28416-82-2;Fluticasone 17beta-Carboxylic Acid;SCHEMBL16718935;CHEBI:175973;DTXSID201113202;(6a,9a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid;(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic acid;BCP12411;MFCD09832931;SY113191;FT-0666822;A855293;(6a,11b,16a,17a)-6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylicacid;(8xi,9xi,10xi,13xi,14xi)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid;1174462-25-9;6,9-diluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic acid;6|A,9|A-Difluoro-11|A,17|A-dihydroxy-16|A-methyl-3-oxoandrosta-1,4-diene-17|A-carboxylic Acid

Chemical Property of (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 303-305°C
• Boiling Point: 568.44oC at 760 mmHg
• PKA: 3.49±0.70(Predicted)
• Flash Point: 297.582oC
• PSA: 94.83000
• Density: 1.388g/cm3
• LogP: 2.36690
• Storage Temp.: Refrigerator
• Solubility.: Acetone (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 396.17483025
• Heavy Atom Count: 28
• Complexity: 824

Purity/Quality:

99% ^*data from raw suppliers

Fluticasone17β-CarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)O)O)C)O)F)C)F
• Description: Fluticasone 17β-carboxylic acid is an intermediate in the synthesis of the glucocorticosteroid fluticasone propionate .
• Uses: The major metabolite of Fluticasone. Anti-inflammatory agent. Fluticasone intermediate. Anti-inflammatory agent

Technology Process of (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic acid

There total 8 articles about (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic acid 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: 100.0%

flumetasone (2135-17-3) → 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid (28416-82-2)

Guidance literature:

With water; periodic acid; In tetrahydrofuran; at 20 ℃; for 1h;

Reference yield: 97.6%

fluticasone (90566-53-3) → 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid (28416-82-2)

Guidance literature:

With water; periodic acid; In tetrahydrofuran; at 20 ℃; for 3h;

Reference yield: 97.0%

→ 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid (28416-82-2)

Guidance literature:

With sodium periodate; water; In tetrahydrofuran; methanol; at 20 - 50 ℃; for 2.41667h;

upstream raw materials:

6α,11β,16α-6,9-difluoro-11,17,21-trihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione

11β,17α,21-trihydroxy-6α,9α-difluoro-16β-methylpregna-1,4-diene-3,20-dione

flumetasone

fluticasone

Downstream raw materials:

6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid

17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene

fluticasone furoate

6α,9-Difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-benzoyl-oxyandrosta-1,4-diene-17β-carbothioic acid

Refernces

• 1、 -. "Preparation method of fluticasone propionate intermediate". Paragraph 0036-0081. . Retrieved 2020/07/13.
• 2、 -. "Synthesis method of fluticasone propionate impurities". Paragraph 0035-0038; 0042-0045. . Retrieved 2019/10/01.