(6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid Chemical Properties

Melting point:

303-305°C

Boiling point:

568.4±50.0 °C(Predicted)

Density 

1.38±0.1 g/cm3(Predicted)

storage temp. 

Refrigerator

solubility 

Acetone (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.49±0.70(Predicted)

color 

White to Off-White

InChIKey

QSVBUQTYFQFEHC-TXKOFOEMNA-N

SMILES

[C@]12(C)C=CC(=O)C=C1[C@@H](F)C[C@@]1([H])[C@]3([H])C[C@@H](C)[C@](O)(C(O)=O)[C@@]3(C)C[C@H](O)[C@]21F |&1:0,8,11,13,16,18,23,26,28,r|

Safety Information

HS Code 

2937220000

(6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid Usage And Synthesis

Description

Fluticasone 17β-carboxylic acid is an intermediate in the synthesis of the glucocorticosteroid fluticasone propionate .

Chemical Properties

White Solid

Uses

The major metabolite of Fluticasone. Anti-inflammatory agent.

Uses

Fluticasone intermediate. Anti-inflammatory agent

General Description

Fluticasone 17β-carboxylic acid ((6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid) is a compound of interest in studying structure-activity relationships within corticosteroid analogs. In research, this compound is examined for its potential interactions with glucocorticoid receptors, given its structural similarity to fluticasone, which is known for its affinity to these receptors. The 17β-carboxylic acid moiety may alter the compound's binding characteristics. In biochemistry, fluticasone 17β-carboxylic acid is used to probe the metabolic pathways of fluticasone, as it may be a metabolite or intermediate.

Synthesis

To a suspension of flumethasone (1.19 g, 2.9 mmol) in tetrahydrofuran (11 ml) was added a solution of periodic acid (2.25 g, 9.9 mmol) in water (5.3 ml). The resulting solution was stirred at RT for 1 h. The tetrahydrofuran was removed in vacuo to leave an aqueous suspension which was filtered, and the solid washed with water and dried to give 1.17 g (100%) of the (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid (Fluticasone 17β-Carboxylic Acid) as a colorless solid.

References

[1] JIADI ZHOU  Weike S  Can Jin. Improved Synthesis of Fluticasone Propionate[J]. Organic Process Research & Development, 2014, 18 8: 928-933. DOI: 10.1021/op5001226

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