Flurandrenolide acetate

Base Information

• Chemical Name: Flurandrenolide acetate
• CAS No.: 2802-11-1
• Molecular Formula: C26H35 F O7
• Molecular Weight: 478.558
• European Community (EC) Number: 220-541-8
• UNII: 0P9257GI1B
• DSSTox Substance ID: DTXSID90950707
• Nikkaji Number: J306.746G
• Wikidata: Q27237057
• NCI Thesaurus Code: C95968
• Metabolomics Workbench ID: 155033
• Mol file: 2802-11-1.mol

Synonyms:FLURANDRENOLIDE ACETATE;Flurandrenolone acetate;2802-11-1;0P9257GI1B;[2-[(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-8-yl]-2-oxoethyl] acetate;UNII-0P9257GI1B;DTXSID90950707;6alpha-Fluoro-11beta,21-dihydroxy-16alpha,17-(isopropylidenedioxy)pregn-4-ene-3,20-dione 21-acetate;EINECS 220-541-8;DB14673;HY-110408;CS-0042447;FLUOCINOLONE ACETONIDE IMPURITY G [EP IMPURITY];Q27237057;1,2-DIHYDRO-9-DESFLUOROFLUOCINOLONE ACETONIDE ACETATE;6.ALPHA.-FLUORO-16.ALPHA.-HYDROXYHYDROCORTISONE 16,17-ACETONIDE 21-ACETATE;2-(12-Fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,3,4,4a,4b,5,6,6a,9a,10,10a,10b,11,12-tetradecahydro-6bH,8H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6b-yl)-2-oxoethyl acetate;6.ALPHA.-FLUORO-11.BETA.-HYDROXY-16.ALPHA.,17-(1-METHYLETHYLIDENEDIOXY)-3,20-DIOXOPREGN-4-EN-21-YL ACETATE;Acetic acid 6alpha-fluoro-11beta-hydroxy-16alpha,17-[(1-methylethylidene)bisoxy]-3,20-dioxopregn-4-en-21-yl ester;PREGN-4-ENE-3,20-DIONE, 21-(ACETYLOXY)-6-FLUORO-11-HYDROXY-16,17-((1-METHYLETHYLIDENE)BIS(OXY))-, (6.ALPHA.,11.BETA.,16.ALPHA.)-

Chemical Property of Flurandrenolide acetate

Chemical Property:

• Boiling Point: 591.5°Cat760mmHg
• Flash Point: 311.5°C
• PSA: 99.13000
• Density: 1.29g/cm³
• LogP: 3.06950
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 478.23668161
• Heavy Atom Count: 34
• Complexity: 974

Purity/Quality:

99% ^*data from raw suppliers

FlurandrenoloneAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C12C(CC3C1(CC(C4C3CC(C5=CC(=O)CCC45C)F)O)C)OC(O2)(C)C
• Isomeric SMILES: CC(=O)OCC(=O)[C@@]12[C@@H](C[C@@H]3[C@@]1(C[C@@H]([C@H]4[C@H]3C[C@@H](C5=CC(=O)CC[C@]45C)F)O)C)OC(O2)(C)C
• Uses: Flurandrenolone Acetate, is the derivative of Flurandrenolide (F598650), which is a Glucocorticoid, used as an antipsoriatic.

Technology Process of Flurandrenolide acetate

There total 7 articles about Flurandrenolide acetate 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:

Fluorocortexolone acetonide (2996-37-4) → 21-acetoxy-6α-fluoro-11β-hydroxy-16α,17-isopropylidenedioxy-pregn-4-ene-3,20-dione (2802-11-1)

Guidance literature:

Multi-step reaction with 2 steps

1: KOH / methanol; CH₂Cl₂

2: 2.) Ba(OAc)2 / 1.) culture of Tieghemella orchidis, 2.) room temp., 20 h

With potassium hydroxide; barium(II) acetate; In methanol; dichloromethane;

DOI:10.1007/BF01152334

Reference yield:

6α-fluoro-11β,16α,17,21-tetrahydroxy-pregn-4-ene-3,20-dione (2022-55-1) → 21-acetoxy-6α-fluoro-11β-hydroxy-16α,17-isopropylidenedioxy-pregn-4-ene-3,20-dione (2802-11-1)

Guidance literature:

With perchloric acid; Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin;

DOI:10.1021/ja01514a072

Reference yield:

6α-fluoro-16α,17,21-trihydroxy-pregn-4-ene-3,20-dione (804-82-0) → 21-acetoxy-6α-fluoro-11β-hydroxy-16α,17-isopropylidenedioxy-pregn-4-ene-3,20-dione (2802-11-1)

Guidance literature:

Multi-step reaction with 2 steps

1: mit Hilfe eines Rindernebennieren-Praeparats

2: perchloric acid / Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin

With perchloric acid;

DOI:10.1021/ja01514a072

upstream raw materials:

6α-fluoro-11β,16α,17,21-tetrahydroxy-pregn-4-ene-3,20-dione

6α-Fluoro-21-hydroxy-16α,17α-isopropenylidenedioxypregn-4-ene-3,20-dione

acetic anhydride

acetic acid

Downstream raw materials:

21-(acetyloxy)-6α-fluoro-11β-hydroxy-16α,17-<(1-methylethylidene)bis(oxy)>pregna-1,4-diene-3,20-dione

Refernces

• 1、 Ryzhkova, V. M.,Gusarova, T. I.,Klubnichkina, G. A.,Garasimova, M. L.,Grinenko, G. S.. "FLUOROSTEROIDS. VI. MICROBIAL 11β-HYDROXYLATION OF 6α-FLUORO-21-HYDROXY-16α,17α-ISOPROPYLIDENEDIOXYPREGN-4-ENE-3,20-DIONE". . p. 881 - 883. Retrieved 2007/10/02.