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
• Article Data: 3

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

1,2-Dihydro Triamcinolone is a derivative of Triamcinolone (T767165), a glucocorticoid, antiasthmatic (inhalant); antiallergic (nasal).

Upstream product

• 2967-24-0 16β,21-diacetoxy-9-fluoro-11β,17-dihydroxy-pregn-4-ene-3,20-dione 
• 98422-57-2 16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione 
• 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 
• 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 
• 23460-76-6 21-acetoxy-pregna-4,9⁽¹¹⁾,16-triene-3,20-dinone 
• 98422-57-2 16β,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione 
• 124-94-7 triamcinolone 
• 127-31-1 Fludrocortisone 
• 426-39-1 16α,21-Diacetoxy-9α-fluoro-11β,17α-dihydroxpregn-4-ene-3,20-dione 

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

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.