337-02-0

Basic information

• Product Name: 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione
• Synonyms: 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione;Pregn-4-ene-3,20-dione, 9-fluoro-11,16,17,21-tetrahydroxy-, (11.beta., 16.alpha.)-;9-Fluoro-11β,16α,17,21-tetrahydroxypregn-4-ene-3,20-dione;(11β,16α)-Fluoro-11,16,17,21-tetrahydroxypregn-4-ene-3,20-dione;9alpha-Fluoro-11beta,16alpha,17alpha,21-tetrahydroxypregn-4-ene-3,20-dione
• CAS NO: 337-02-0
• Molecular Formula: C₂₁H₂₉FO₆
• Molecular Weight: 396.4497632
• EINECS: 206-411-3
• Mol File: 337-02-0.mol

Chemical Properties

• Melting Point: 257-260 °C (decomp)
• Boiling Point: 585.2°Cat760mmHg
• Flash Point: 307.7°C
• Appearance: /
• Density: 1.39g/cm³
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Pyridine (Slightly)
• PKA: 11.58±0.70(Predicted)
• CAS DataBase Reference: 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione(337-02-0)
• EPA Substance Registry System: 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione(337-02-0)

Safety Data

• Hazardous Substances Data: 337-02-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9-fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione is used as a pharmaceutical compound for its glucocorticoid activity. It serves as an anti-inflammatory agent, which can be beneficial in treating various inflammatory conditions and autoimmune disorders. 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione's structure allows it to modulate the immune system and reduce inflammation, making it a valuable asset in the development of medications for asthma, allergies, and other related conditions.
Used in Steroid Research:
In the field of steroid research, 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione can be used as a starting material or a reference compound for the synthesis and development of new steroidal drugs. Its unique structure provides opportunities for further modification and optimization, potentially leading to the discovery of novel therapeutic agents with improved efficacy and reduced side effects.
Used in Drug Delivery Systems:
Similar to gallotannin, 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione can be incorporated into drug delivery systems to enhance its bioavailability and therapeutic outcomes. By employing various organic and metallic nanoparticles as carriers, the compound can be effectively delivered to target cells or tissues, improving its overall efficacy and reducing potential side effects.

Upstream product

• 127-31-1 Fludrocortisone 
• 802-71-1 (8S,9R,10S,11S,13S,14S)-9-Fluoro-11-hydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15-dodecahydro-cyclopenta[a]phenanthren-3-one 
• 50-03-3 hydrocortisone acetate 
• 23460-76-6 21-acetoxy-pregna-4,9⁽¹¹⁾,16-triene-3,20-dinone 
• 98422-57-2 16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione 
• 98422-57-2 16β,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione 
• 2967-24-0 16β,21-diacetoxy-9-fluoro-11β,17-dihydroxy-pregn-4-ene-3,20-dione 
• 426-39-1 16α,21-Diacetoxy-9α-fluoro-11β,17α-dihydroxpregn-4-ene-3,20-dione 
• 98632-54-3 16α,21-diacetoxy-17-hydroxy-pregna-4,9(11)-diene-3,20-dione 
• 91160-85-9 16α,21-diacetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione 
• 74220-43-2 21-Acetoxy-16α,17α-dihydroxy-4,9(11)-pregnadien-3,20-dion 
• 124-94-7 triamcinolone 

Downstream Products

• 1524-86-3 16α-17-[(1-methylethylidene)bis(oxy)]-11β,21-dihydroxy-9-fluoro-4-ene-pregna-3,20-dione 

Relevant articles and documents

Preparation method of halcinonide and derivative thereof

The invention provides a preparation method of halcinonide and a derivative thereof. The method comprises the following steps: taking hydrocortisone acetate as a raw material, performing dehydration and then epoxidation on the raw material, performing ring opening, performing hydrolysis and chlorination, and then performing oxidation and ketalization, so as to obtain halcinonide; or performing dehydration and then epoxidation on the raw material, performing ring opening, performing hydrolysis, and then performing oxidation and ketalization, so as to obtain 9-fluoro-16a,17-(isopropylidenedioxy)corticosterone. In ring opening fluorination unit reaction, safe and mild reaction environment is selected, a fluorizating agent with low concentration is used as a reaction reagent, the reaction rate is effectively controlled, the production of side reaction products is restrained, and the product quality and yield are greatly improved. Moreover, in 16, 17-ketalization unit reaction, an acid catalyst which is low in toxicity and easy to control is adopted to replace boron trifluoride with high toxicity to perform catalysis, and the catalytic effect is effectively improved.

Synthesis and structure elucidation of potential 6-oxygenatedated metabolites of (22R)-6*9α-difluoro-11β,21-dihydroxy-16α,17α-propylmethylenedioxypregn-4 -ene-3,20-dione, and related glucocorticosteroids

(22R)-6α,9α-Difluoro-11β,21-dihydroxy-16α,17α-propylmethylenedioxypregn- 4-ene-3,20-dione (rofleponide) is a synthetic glucocorticosteroid with high affinity for the rat thymus glucocorticoid receptor and a very high biotransformation rate demonstrated through incubation with a human liver S9 subcellular fraction. Because oxidation in the 6-position is an important metabolic pathway of glucocorticosteroids, the potential 6β-hydroxy and 6-oxo metabolites of rofleponide were synthesized to be used as reference compounds. Three alternative routes were used to reach the 6-hydroxy compound: (a) a one-step procedure involving allylic oxidation of rofleponide by selenium dioxide, (b) selenium dioxide oxidation of the corresponding 1,4-diene followed by selective 1,2-hydrogenation using Wilkinson's catalyst, and (c) autoxidation of a 3-methoxypregna-3,5-diene derivative. All three routes proceeded stereospecifically. Routes (a) and (c) gave approximately the same overall yield of the 6β-hydroxy epimer, whereas the overall yield from route (b) was much lower, primarily because of incomplete 1,2-hydrogenation. The 6-oxo compound was prepared through Pfitzner/Moffat oxidation of the 6-hydroxy compound. The stereochemistry of the 6-hydroxy substituent is discussed on the basis of 1H-NMR spectroscopy and supplementary 2D NOESY experiments. Copyright (C) 2000 Elsevier Science Inc.

Fluorinated steroids

Disclosed are the 22R and 22S epimers of compounds of the formula STR1 wherein X1 represents a fluorine atom, and X2 represents a hydrogen atom or a fluorine atom. Also disclosed are processes for the preparation of the compounds, pharmaceutical compositions comprising the compounds and methods of treatment of inflammatory and allergic conditions employing the compounds.