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192569-17-8

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  • (11α,17α)-11,17-Dihydroxy-3-oxopregna-4,6-diene-21-carboxylic acid-τ-lactone

    Cas No: 192569-17-8

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192569-17-8 Usage

Chemical Properties

Yellow Crystalline Solid

Uses

11α-Hydroxy Canrenone is the key intermediate in the synthesis of Eplerenone, a cardiovascular drug. Canrenone was biotransformed into 11α-Hydroxycanrenone by Aspergillus ochraceus SIT34205.

Check Digit Verification of cas no

The CAS Registry Mumber 192569-17-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,2,5,6 and 9 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 192569-17:
(8*1)+(7*9)+(6*2)+(5*5)+(4*6)+(3*9)+(2*1)+(1*7)=168
168 % 10 = 8
So 192569-17-8 is a valid CAS Registry Number.
InChI:InChI=1/C22H28O4/c1-20-8-5-14(23)11-13(20)3-4-15-16-6-9-22(10-7-18(25)26-22)21(16,2)12-17(24)19(15)20/h3-4,11,15-17,19,24H,5-10,12H2,1-2H3/t15?,16?,17-,19?,20+,21+,22-/m1/s1

192569-17-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 11α-Hydroxy Canrenone

1.2 Other means of identification

Product number -
Other names 11-α-Hydroxycarvenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:192569-17-8 SDS

192569-17-8Synthetic route

canrenone
976-71-6

canrenone

11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

Conditions
ConditionsYield
With D-glucose; peptone In water90%
With D-glucose In water for 72h;80%
With D-glucose In water for 72h;80%
Reaxys ID: 13210058

Reaxys ID: 13210058

11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

canrenone
976-71-6

canrenone

A

11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

B

C22H28O5
1363502-03-7

C22H28O5

Conditions
ConditionsYield
With Aspergillus ochraceus SIT34205 at 28℃; for 50h;
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

11α-(methylsulphonyl)oxy-canrenone
209253-91-8

11α-(methylsulphonyl)oxy-canrenone

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 2h;98%
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

nitromethane
75-52-5

nitromethane

11β,17β-dihydroxy-7α-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
1398078-03-9

11β,17β-dihydroxy-7α-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

Conditions
ConditionsYield
With benzalkonium chloride; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 48h; stereoselective reaction;90%
With benzalkonium chloride; potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; for 48h; Reagent/catalyst;90%
2-methylfuran
534-22-5

2-methylfuran

11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

11α,17β-dihydroxy-7α-(5'-methyl-2'-furyl)-3-oxo-pregn-4-ene-21-carboxylic acid γ-lactone
610785-47-2

11α,17β-dihydroxy-7α-(5'-methyl-2'-furyl)-3-oxo-pregn-4-ene-21-carboxylic acid γ-lactone

Conditions
ConditionsYield
With ethanol; boron trifluoride diethyl etherate In nitromethane; dichloromethane at -17℃; for 20h;86.2%
With ethanol; boron trifluoride diethyl etherate In nitromethane at -20 - -17℃; for 20h;
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

nitromethane
75-52-5

nitromethane

A

11β,17β-dihydroxy-7α-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
1398078-03-9

11β,17β-dihydroxy-7α-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

B

11β,17β-dihydroxy-7β-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
1398078-09-5

11β,17β-dihydroxy-7β-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; Reagent/catalyst; Temperature; Time;A 25%
B 15%
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

sodium cyanide
143-33-9

sodium cyanide

4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile
192704-54-4

4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile

Conditions
ConditionsYield
With sulfuric acid In ISOPROPYLAMIDE; water at 95℃; for 18.5h;3 g
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

5α,17β-dihydroxy-3-oxo-pregn-9(11)-ene-7α,21-dicarboxylic acid bis-γ-lactone
610785-45-0

5α,17β-dihydroxy-3-oxo-pregn-9(11)-ene-7α,21-dicarboxylic acid bis-γ-lactone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: triethylamine / dichloromethane / 2 h / 0 °C
2: potassium acetate / formic acid; acetic anhydride / 4 h / 100 °C
3: copper(I) iodide-lithium chloride; boron trifluoride diethyl etherate / tetrahydrofuran
4: potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate / tetrahydrofuran; methanol; water / 14 h / 20 - 50 °C
5: methyltrifluoromethyldioxirane / dichloromethane / 2 h / -25 °C
6: dipyridinium dichromate / dichloromethane / 20 °C / Molecular sieve
View Scheme
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

C28H42O4Si

C28H42O4Si

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 2 h / 0 °C
2: potassium acetate / formic acid; acetic anhydride / 4 h / 100 °C
3: copper(I) iodide-lithium chloride; boron trifluoride diethyl etherate / tetrahydrofuran
View Scheme
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

17β-hydroxy-7α-methylene-5α-oxo-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone
1263102-65-3

17β-hydroxy-7α-methylene-5α-oxo-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 2 h / 0 °C
2: potassium acetate / formic acid; acetic anhydride / 4 h / 100 °C
3: copper(I) iodide-lithium chloride; boron trifluoride diethyl etherate / tetrahydrofuran
4: potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate / tetrahydrofuran; methanol; water / 14 h / 20 - 50 °C
View Scheme
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

17β-hydroxy-7α-(1'-hydroxy)methylene-5α-oxo-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone
1263102-67-5

17β-hydroxy-7α-(1'-hydroxy)methylene-5α-oxo-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine / dichloromethane / 2 h / 0 °C
2: potassium acetate / formic acid; acetic anhydride / 4 h / 100 °C
3: copper(I) iodide-lithium chloride; boron trifluoride diethyl etherate / tetrahydrofuran
4: potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate / tetrahydrofuran; methanol; water / 14 h / 20 - 50 °C
5: methyltrifluoromethyldioxirane / dichloromethane / 2 h / -25 °C
View Scheme
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

Δ9(11)-canrenone
95716-71-5

Δ9(11)-canrenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 2 h / 0 °C
2: potassium acetate / formic acid; acetic anhydride / 4 h / 100 °C
View Scheme
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / 0 - 20 °C
4.1: triethylamine / dichloromethane / 0 °C
5.1: potassium formate; formic acid / acetic anhydride / 100 °C
6.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / 0 - 20 °C
4.1: triethylamine / dichloromethane / 0 °C
5.1: potassium formate; formic acid / acetic anhydride / 100 °C
6.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: potassium carbonate; benzalkonium chloride; nitromethane / N,N-dimethyl-formamide / 48 h / 90 °C
3.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
3.2: 4 h
4.1: potassium carbonate / 0 - 20 °C
5.1: triethylamine / dichloromethane / 0 °C
6.1: potassium formate; formic acid / acetic anhydride / 100 °C
7.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 - 100 °C
2.1: sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / acetone / 0 - 20 °C
4.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
5.1: acetic anhydride; potassium formate; formic acid / 19 h / 70 - 100 °C / Inert atmosphere
6.1: dipotassium hydrogenphosphate; dihydrogen peroxide; trichloroacetamide / dichloromethane / 24 h / 0 - 15 °C / pH 9
View Scheme
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
192704-56-6

11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: potassium carbonate; benzalkonium chloride; nitromethane / N,N-dimethyl-formamide / 48 h / 90 °C
3.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
3.2: 4 h
4.1: potassium carbonate / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 - 100 °C
2.1: sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / acetone / 0 - 20 °C
View Scheme
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

methyl hydrogen 17α-hydroxy-11α-(methylsulfonyl)oxy-3-oxopregn-4-ene-7α,21-dicarboxylate, γ-lactone
192704-58-8

methyl hydrogen 17α-hydroxy-11α-(methylsulfonyl)oxy-3-oxopregn-4-ene-7α,21-dicarboxylate, γ-lactone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / 0 - 20 °C
4.1: triethylamine / dichloromethane / 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / 0 - 20 °C
4.1: triethylamine / dichloromethane / 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: potassium carbonate; benzalkonium chloride; nitromethane / N,N-dimethyl-formamide / 48 h / 90 °C
3.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
3.2: 4 h
4.1: potassium carbonate / 0 - 20 °C
5.1: triethylamine / dichloromethane / 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 - 100 °C
2.1: sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / acetone / 0 - 20 °C
4.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
View Scheme
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester
95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / 0 - 20 °C
4.1: triethylamine / dichloromethane / 0 °C
5.1: potassium formate; formic acid / acetic anhydride / 100 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / 0 - 20 °C
4.1: triethylamine / dichloromethane / 0 °C
5.1: potassium formate; formic acid / acetic anhydride / 100 °C
View Scheme
Multi-step reaction with 6 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: potassium carbonate; benzalkonium chloride; nitromethane / N,N-dimethyl-formamide / 48 h / 90 °C
3.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
3.2: 4 h
4.1: potassium carbonate / 0 - 20 °C
5.1: triethylamine / dichloromethane / 0 °C
6.1: potassium formate; formic acid / acetic anhydride / 100 °C
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 - 100 °C
2.1: sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / acetone / 0 - 20 °C
4.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
5.1: acetic anhydride; potassium formate; formic acid / 19 h / 70 - 100 °C / Inert atmosphere
View Scheme
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

9α,11α-epoxy-17β-hydroxypregn-4-en-3-one-7α,21-dicarboxylic acid γ-lactone
209253-72-5

9α,11α-epoxy-17β-hydroxypregn-4-en-3-one-7α,21-dicarboxylic acid γ-lactone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
View Scheme
Multi-step reaction with 2 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
View Scheme
Multi-step reaction with 3 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: potassium carbonate; benzalkonium chloride; nitromethane / N,N-dimethyl-formamide / 48 h / 90 °C
3.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
3.2: 4 h
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 - 100 °C
2.1: sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 45 °C
2.2: 4 h
View Scheme

192569-17-8Upstream product

192569-17-8Relevant articles and documents

Development of a high-yielding bioprocess for 11-α hydroxylation of canrenone under conditions of oxygen-enriched air supply

Contente, Martina Letizia,Guidi, Benedetta,Serra, Immacolata,De Vitis, Valerio,Romano, Diego,Pinto, Andrea,Lenna, Roberto,de Souza Oliveira, Ricardo Pinheiro,Molinari, Francesco

, p. 1 - 4 (2016)

A high yielding bioprocess for 11-α hydroxylation of canrenone (1a) using Aspergillus ochraceus ATCC 18500 was developed. The optimization of the biotransformation involved both fermentation (for achieving highly active mycelium of A. ochraceus) and biotransformation with the aim to obtain 11-α hydroxylation with high selectivity and yield. A medium based on sucrose as C-source resulted particularly suitable for conversion of canrenone into the corresponding 11-hydroxy derivative, whereas the use of O2-enriched air and dimethyl sulfoxide (DMSO) as a co-solvent for increasing substrate solubility played a crucial role for obtaining high yields (>95%) of the desired product in high chemical purity starting from 30?mM (10.2?g/L) of substrate. The structure of the hydroxylated product was confirmed by a combination of two-dimensional NMR proton-proton correlation techniques.

Processes for preparation of 3-keto-7alpha-alkoxycarbonyl-delta-4,5- steroids and intermediates useful therein

-

Example 16, (2008/06/13)

Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of Formula I wherein:-A-A- represents the group -CHR4-CHR5- or -CR4=CR5- R3, R4 and R5 are independently selected from the group consisting of hydrogen, halo, hydroxy, lower alkyl, lower alkoxy, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, cyano, varyloxy;R1 represents an alpha-oriented lower alkoxycarbonyl or hydroxyalkyl radical;-B-B- represents the group -CHR6-CHR7- or an alpha- or beta- oriented group: where R6 and R7 are independently selected from the group consisting of hydrogen, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy; andR8 and R9 are independently selected from the group consisting of hydrogen, hydroxy, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy, or R8 and R9 together comprise a carbocyclic or heterocyclic ring structure, or R8 or R9 together with R6 or R7 comprise a carbocyclic or heterocyclic ring structure fused to the pentacyclic D ring.

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