9-Fluoro-11beta,21-dihydroxy-16alpha,17-(isopropylidenedioxy)pregn-4-ene-3,20-dione

Base Information

• Chemical Name: 9-Fluoro-11beta,21-dihydroxy-16alpha,17-(isopropylidenedioxy)pregn-4-ene-3,20-dione
• CAS No.: 1524-86-3
• Molecular Formula: C24H33FO6
• Molecular Weight: 436.521
• European Community (EC) Number: 216-195-2
• NSC Number: 21915
• UNII: UX031M662V
• DSSTox Substance ID: DTXSID001118751
• Nikkaji Number: J206.734J
• Wikidata: Q27116120
• Mol file: 1524-86-3.mol

Synonyms:1524-86-3;9-Fluoro-16a,17-(isopropylidenedioxy)corticosterone;9-Fluoro-11beta,21-dihydroxy-16alpha,17-(isopropylidenedioxy)pregn-4-ene-3,20-dione;NSC 21915;UNII-UX031M662V;UX031M662V;EINECS 216-195-2;NSC-21915;11beta,16alpha,17alpha,21-Tetrahydroxy-9alpha-fluoropregn-4-ene-3,20-dione 16,17-acetonide;(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one;Pregn-4-ene-3,20-dione, 9-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone;MLS002638824;Hydrotriamcinolone acetate;SCHEMBL8904914;CHEBI:34509;2H-Naphth[2',1':4,5]indeno[1,2-d][1,3]dioxole, pregn-4-ene-3,20-dione deriv.;DTXSID001118751;BCP20556;NSC21915;Pregn-4-ene-3,20-dione, 9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)-, (11.beta.,16.alpha.)-;Triamcinolone Acetonide EP Impurity E;AKOS015901715;AC-3523;Corticosterone,17-(isopropylidenedioxy)-;1,2-DIHYDROTRIAMCINOLONE ACETONIDE;9|A-Fluoro-11|A,16|A,17|A,21-tetrahydroxy-pregna-4-ene-3,20-dione cyclic16,17-acetal with acetone;(+)-1,2-DIHYDROTRIAMCINOLONE ACETONIDE;A854243;Q-101383;Q27116120;TRIAMCINOLONE ACETONIDE IMPURITY E [EP IMPURITY];9-Fluoro-16alpha,17-(isopropylidenedioxy) Corticosterone;2H-Naphth[2',5]indeno[1,2-d][1,3]dioxole, pregn-4-ene-3,20-dione deriv.;9-Fluoro-11b,21-dihydroxy-16a,17-(isopropylidenedioxy)pregn-4-ene-3,20-dione;CORTICOSTERONE, 9-FLUORO-16.ALPHA.,17-DIHYDROXY-, CYCLIC 16,17-ACETAL WITH ME2CO;Pregn-4-ene-3, 9-fluoro-11.beta.,21-dihydroxy-16.alpha.,17-(isopropylidenedioxy)-;(11beta,16alpha)-9-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione;1,2-dihydrotriamcinoloneacetonide;9-fluoro-11?,21-dihydroxy-16?,17-(1-methylethylidenedioxy)pregna-4-ene-3,20-dione;(1S,2S,4R,8S,9S,11S,12R,13S)-12-Fluoro-8-(2-glycoloyl)-11-hydroxy-6,6,9,13-tetramethyl-5.7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one;11.BETA.,16.ALPHA.,17.ALPHA.,21-TETRAHYDROXY-9.ALPHA.-FLUOROPREGN-4-ENE-3,20-DIONE 16,17-ACETONIDE;9-FLUORO-11.BETA.,21-DIHYDROXY-16.ALPHA.,17- (ISOPROPYLIDENEDIOXY)PREGN-4-ENE-3,20-DIONE;9-Fluoro-11beta,21-dihydroxy-16alpha,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione;Pregn-4-ene-3, 9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)-, (11.beta.,16.alpha.)-;Pregn-4-ene-3, 9-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone;PREGN-4-ENE-3,20-DIONE, 9-FLUORO-11,21-DIHYDROXY-16,17-((1-METHYLETHYLIDENE)BIS(OXY))-, (11.BETA.,16.ALPHA.)-

Chemical Property of 9-Fluoro-11beta,21-dihydroxy-16alpha,17-(isopropylidenedioxy)pregn-4-ene-3,20-dione

Chemical Property:

• Boiling Point: 575.7 °C at 760 mmHg
• Flash Point: 302 °C
• Density: 1.31 g/cm³
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 436.22611693
• Heavy Atom Count: 31
• Complexity: 883

Purity/Quality:

99% ^*data from raw suppliers

9-Fluoro-16α,17-(isopropylidenedioxy)Corticosterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2CC3C4CCC5=CC(=O)CCC5(C4(C(CC3(C2(O1)C(=O)CO)C)O)F)C)C
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@]2([C@H](C[C@]4([C@H]3C[C@@H]5[C@]4(OC(O5)(C)C)C(=O)CO)C)O)F
• Uses: 9-Fluoro-16α,17-(isopropylidenedioxy) Corticosterone (Triamcinolone Acetonide EP Impurity E) is a synthetic fluorinated corticosteroid tested for inhibition of granuloma in rats and for vasoconstriction activity in human subjects; potential topical antiinflammatory agent. Synthetic fluorinated corticosteroid tested for inhibition of granuloma in rats and for vasoconstriction activity in human subjects; potential topical antiinflammatory agent.

Technology Process of 9-Fluoro-11beta,21-dihydroxy-16alpha,17-(isopropylidenedioxy)pregn-4-ene-3,20-dione

There total 16 articles about 9-Fluoro-11beta,21-dihydroxy-16alpha,17-(isopropylidenedioxy)pregn-4-ene-3,20-dione 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: 52.0%

9β,11β-epoxy-21-hydroxy-16α,17-(isopropylidenedioxy)pregn-4-ene-3,30-dione (160512-81-2) → 16α-17-[(1-methylethylidene)bis(oxy)]-11β,21-dihydroxy-9-fluoro-4-ene-pregna-3,20-dione (1524-86-3)

Guidance literature:

With hydrogen fluoride;

DOI:10.1021/jo00103a063

Reference yield: 44.0%

9α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione (337-02-0) + acetone (67-64-1) → 16α-17-[(1-methylethylidene)bis(oxy)]-11β,21-dihydroxy-9-fluoro-4-ene-pregna-3,20-dione (1524-86-3)

Guidance literature:

With hydrogen bromide; at 15 ℃; Reagent/catalyst; Temperature;

Reference yield:

C21H28O6 + acetone (67-64-1) → 16α-17-[(1-methylethylidene)bis(oxy)]-11β,21-dihydroxy-9-fluoro-4-ene-pregna-3,20-dione (1524-86-3)

Guidance literature:

acetone; With hydrogen fluoride; In water; at -40 - 30 ℃; for 1h; Green chemistry;

C₂₁H₂₈O₆; In water; at -35 - 30 ℃; for 0.166667h; Green chemistry;

With potassium carbonate; In water; at 10 ℃; for 1h; Green chemistry;

upstream raw materials:

9α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione

9β,11β-epoxy-21-hydroxy-16α,17-(isopropylidenedioxy)pregn-4-ene-3,30-dione

9-bromo-11β-hydroxy-16α,17-(isopropylidenedioxy)-3,20-dioxopregn-4-en-21-yl formate

16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione

Downstream raw materials:

21-acetoxy-6α-chloro-9-fluoro-11β-hydroxy-16α,17-isopropylidenedioxy-pregna-1,4-diene-3,20-dione

halcinonide

triamcinolone acetonide

Refernces

• 1、 -. "Preparation method of halcinonide and derivative thereof". . . Retrieved 2018/03/26.
• 2、 -. "Steroid esters". . . Retrieved 2008/06/13.