ChemicalBook > Product Catalog >Organic Chemistry >Carboxylic acids and derivatives >(6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid

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

(6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid Structure
CAS No.
28416-82-2
Chemical Name:
(6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid
Synonyms
FluMethasone acid;Fluticasone Acid;Axon 1170;impurity J;BNKY011-FP01;BNKY012-FF01;Flumetasone acid;flumethason acid;(6a,11b,16a,17a)-6;17-carboxylic acid
CBNumber:
CB2854948
Molecular Formula:
C21H26F2O5
Molecular Weight:
396.42
MOL File:
28416-82-2.mol
MSDS File:
SDS
Modify Date:
2024/6/29 22:56:24

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

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H332-H335
Precautionary statements  P261-P280-P305+P351+P338
HS Code  2937220000

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

Description

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

Chemical Properties

White Solid

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

(6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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6a,9a-Difluoro-11b,17a-dihydroxy-16a-methylpregna- 3-oxo-1,4-diene-17b-carboxylic Acid Fluticasone 17b-Carboxylic Acid 6A,9A-DIFLUORO-11SS,17A-DIHYDROXY-3-OXOANDROSTA-1,4-DIENE-17SS-CARBOXYLIC ACID ANDROSTA-1,4-DIENE-17-CARBOXYLIC ACID,6,9-DIFLUORO-11,17- DIHYDROXY-16-METHYL-3-OXO-,(6ALPHA,11BETA,16ALPHA,17ALPHA)- ANDROSTA-1,4-DIENE-17-CARBOXYLIC ACID,6,9-DIFLUORO-11,17- DIHYDROXY-16-METHYL-3-OXO-,(6A,11SS,16A,17A)- (6a,11,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxo-androsta-1,4-diene-17-carboxylic Acid 6a,9a-Difluoro-11,17a-dihydroxy-16a-methylpregna-3-oxo-1,4-diene-17-carboxylic Acid Fluticasone 17-Carboxylic Acid (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-M 6a,9a-difluoro-11 P,17a-dihydroxy-16a-methyl-3- oxoandrosta-1,4-diene-17P-carboxylic acid 6α,9α-Difluoro-11β-,17α-dihydroxy-3-oxoandrosta-1,4-diene-17-carboxylic Acid Discontinued see product # F599490 Androsta-1,4-diene-17-carboxylic acid,6,9-difluoro-11,17- dihydroxy-16-Methyl-3-oxo-,(6|á,11|,16|á,17|á)- (6α,11β,16α,17α)-6,9-Difluoro-11,17-dihydroxy-16-Methyl-3-oxo-androsta-1,4-diene-17-carboxylic Acid 6α,9α-Difluoro-11β,17α-dihydroxy-16α-Methylpregna- 3-oxo-1,4-diene-17β-carboxylic Acid (6A,11B,16A,17A)-6,9-DIFLUORO-11,17-diHYDROXY-16-METHY1-3-OXOANDROSTA-1,4-DIENE-17-CAR (6a,9a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-DIFLUORO-11,17-DIHYDRO Fluticasone propionate Intermediates (Flumethasone acid) Fluticasone Carboxylic Acid (6a,9a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid (6a,9a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxyl (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid ANDROSTA-1,4-DIENE-17-CARBOXYLIC ACID,6,9-DIFLUORO-11,17- DIHYDROXY-16-METHYL-3-OXO-,(6α,11β,16α,17α)- 6a,9a-Difluoro-1117a-dihydroxy-3-oxoandrosta-1,4-diene-17carboxylic Acid Discontinued see product # F599490 Axon 1170 impurity J 6α,9-Difluoro-11β-hydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carboxylic acid Fluticasone Impurity 11(Fluticasone USP RC J) Fluticasone USP RC J Fluticasone 17-beta-Carboxylic Acid BNKY011-FP01 BNKY012-FF01 Propionate Impurity J (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R) Fluticasone USP Related Compound J Fluticasone IMpurity J Fluticasone Propionate Impurity 1 1,4-diene-17-carboxylic acid (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid [Flumethasone Acid] 6α,9α-Difluoro-11β-,17α-dihydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic Acid Discontinued see product # F599490 Fluticasone 17β-Carboxylic Acid Flumetasone acid FLUMETHASONE ACID /CAS NO.:28416-82-2 6α,9α-Difluoro-11β-,17α-dihydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic Acid Discontinued see F599490 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid Fluticasone Related Compound J (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-ox... Androsta-1,4-diene-17-carboxylic acid,6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxo-, (6a,11b,16a,17a)- (6S,9R,10S,11S,13S,16R,17R)-6,9-Difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid Fluticasone Propionate Related Compound J (6alpha, 9alpha-difluoro-11beta,17alpha-dihydroxy-16alpha (1285818) FluMethasone acid Fluticasone Acid flumethason acid Fluticasone Propionate USP Related Compound J (6a,11b,16a,17a)-6 Androsta-1,4-diene-17-carboxylic acid, 6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxo-, (6α,11β,16α,17α)- Fluticasone Propionate Impurity 6