10184-70-0

Basic information

• Product Name: ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11 )-DEHYDROCORTISOL)
• Synonyms: ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11 )-DEHYDROCORTISOL);21-Desacetyl Anecortave;17-Desacetyl Anecortave;17,21-Dihydroxypregna-4,9(11)-diene-3,20-dione;AL 4940
• CAS NO: 10184-70-0
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.44462
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 10184-70-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 231-233 °C(Solv: tetrahydrofuran (109-99-9))
• Boiling Point: 540.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.24±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated)
• PKA: 12.52±0.60(Predicted)
• CAS DataBase Reference: ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11 )-DEHYDROCORTISOL)(CAS DataBase Reference)
• NIST Chemistry Reference: ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11 )-DEHYDROCORTISOL)(10184-70-0)
• EPA Substance Registry System: ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11 )-DEHYDROCORTISOL)(10184-70-0)

Safety Data

• Hazardous Substances Data: 10184-70-0(Hazardous Substances Data)

Usage

Description

ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11)-DEHYDROCORTISOL), also known as 17-Desacetyl Anecortave, is a derivative of Anecortave Acetate (A637640). It exhibits glucocorticoid and mineralocorticoid receptor binding activities, which are essential for its various applications in different industries.

Uses

Used in Pharmaceutical Industry:
ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11)-DEHYDROCORTISOL) is used as a pharmaceutical compound for its glucocorticoid and mineralocorticoid receptor binding activities. These activities make it a potential candidate for the treatment of various medical conditions related to inflammation, immune response, and fluid balance regulation.
Used in Research and Development:
In the field of research and development, ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11)-DEHYDROCORTISOL) is used as a research tool for studying the mechanisms of glucocorticoid and mineralocorticoid receptors. This understanding can lead to the development of new therapeutic strategies and drugs targeting these receptors.
Used in Drug Delivery Systems:
Similar to Gallotannin, ANECORTAVE ACETATE RELATED COMPOUND A (20 MG) (9(11)-DEHYDROCORTISOL) can also be employed in drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes. By incorporating this compound into various carriers, such as organic and metallic nanoparticles, its efficacy in treating specific conditions can be improved.

Synthetic route

anecortave (7753-60-8) → Anecortave (10184-70-0)

Conditions	Yield
With methanol; potassium carbonate
With potassium carbonate In methanol; water 1 h, room t., 50 min, 40 deg C;	5.33 g

21-acetoxy-3,3;20,20-bis-ethanediyldioxy-pregna-5,9(11)-dien-17-ol (428516-04-5) → Anecortave (10184-70-0)

Conditions	Yield
With sulfuric acid

Nicotinic acid (8S,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (119669-94-2) → Anecortave (10184-70-0)

Conditions	Yield
With potassium carbonate In methanol

anecortave (7753-60-8) → Anecortave (10184-70-0) + pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (4380-55-6) + (10S,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one (10184-69-7) + pregna-1,4,9(11)-triene-17α,20β,21-triol-3-one

Conditions	Yield
With Nocardioides simplex VKM Ac-2033D In phosphate buffer at 28℃; pH=7.5; Product distribution; Further Variations:; pH-values; Enzymatic reaction;

Nicotinic acid (8S,9R,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-9-chloro-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (108674-98-2) → Anecortave (10184-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: AgBF4 / acetone 2: K2CO3 / methanol View Scheme

Epicortisol (566-35-8) → Anecortave (10184-70-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: dann mit Methansulfonylchlorid 2: sodium acetate; acetic acid 3: K2CO3; methanol View Scheme

21-acetoxy-17-hydroxy-11α-methanesulfonyloxy-pregn-4-ene-3,20-dione (113862-93-4) → Anecortave (10184-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate; acetic acid 2: K2CO3; methanol View Scheme

21-acetoxy-3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17-diol (74220-42-1) → Anecortave (10184-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphoryl chloride; pyridine 2: aqueous ethanol.H2SO4 View Scheme

3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17,21-triol (76338-54-0) → Anecortave (10184-70-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine 2: phosphoryl chloride; pyridine 3: aqueous ethanol.H2SO4 View Scheme

methanolic potassium hydroxide + anecortave (7753-60-8) → Anecortave (10184-70-0)

Conditions	Yield
In methanol; dichloromethane

Anecortave (10184-70-0) → androst-4,9(11)-dien-3,17-dione (1035-69-4)

Conditions	Yield
With sodium bismuthate	87%
With manganese(IV) oxide In chloroform for 4h; Heating;	72.6%

Anecortave (10184-70-0) + acetic anhydride (108-24-7) → anecortave (7753-60-8)

Conditions	Yield
With pyridine

Anecortave (10184-70-0) + acetylating agent → anecortave (7753-60-8)

Anecortave (10184-70-0) → hydroxy-17β androstadiene-4,9(11) one-3,7 (2398-99-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C View Scheme

Anecortave (10184-70-0) → androstatriene-4,8,14 diol-3β,17β (105276-62-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h 5: 0.074 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 1 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 76 percent / hydrofluoric acid, BF3 / CH2Cl2 / 16 h / -30 °C 5: 0.074 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 1 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h 5: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -30 deg C, 1.5 h; 2.) 1 h 6: 0.074 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 1 h / 20 °C View Scheme

Anecortave (10184-70-0) → methyl-14β, nor-18(13β) androstadiene-4,8 dione-3,17 (105276-63-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h 5: 44 percent / hydrofluoric acid / CH2Cl2 / 18 h / -15 °C View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 76 percent / hydrofluoric acid, BF3 / CH2Cl2 / 16 h / -30 °C 5: 44 percent / hydrofluoric acid / CH2Cl2 / 18 h / -15 °C View Scheme
Multi-step reaction with 6 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h 5: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -30 deg C, 1.5 h; 2.) 1 h 6: 44 percent / hydrofluoric acid / CH2Cl2 / 18 h / -15 °C View Scheme

Anecortave (10184-70-0) → hydroxy-17β androstatriene-4,8,14 one-3 (105276-61-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h View Scheme
Multi-step reaction with 4 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 76 percent / hydrofluoric acid, BF3 / CH2Cl2 / 16 h / -30 °C View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h 5: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -30 deg C, 1.5 h; 2.) 1 h View Scheme

Anecortave (10184-70-0) → androstatriene-4,8,14 dione-3,17 (105369-18-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h 5: 0.008 g / Jones reagent / acetone / 0.17 h / 0 °C View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 76 percent / hydrofluoric acid, BF3 / CH2Cl2 / 16 h / -30 °C 5: 0.008 g / Jones reagent / acetone / 0.17 h / 0 °C View Scheme
Multi-step reaction with 6 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h 5: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -30 deg C, 1.5 h; 2.) 1 h 6: 0.008 g / Jones reagent / acetone / 0.17 h / 0 °C View Scheme

Anecortave (10184-70-0) → epoxy-9α,11α hydroxy-17β androstene-4 one-3 (105276-59-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C View Scheme

Anecortave (10184-70-0) → dihydroxy-9α,17β fluoro-11β androstene-4 one-3

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h View Scheme

Anecortave (10184-70-0) → acetoxy-17β androstatriene-4,8,14 one-3 (105306-04-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -18 deg C, 4 h; 2.) -15 deg C, 2 h 5: 0.035 g / pyridine View Scheme
Multi-step reaction with 5 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 76 percent / hydrofluoric acid, BF3 / CH2Cl2 / 16 h / -30 °C 5: 0.035 g / pyridine View Scheme
Multi-step reaction with 6 steps 1: 87 percent / sodium bismutate 2: 0.695 g / lithium tritertiobutoxy aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 82 percent / p-nitroperbenzoic acid / CH2Cl2 / 12 h / 0 °C 4: 71 percent / hydrofluoric acid / CH2Cl2 / 2 h, 0 deg C then alloved to warm to room t. over 14 h 5: 1.) hydrofluoric acid; 2.) BF3 / 1.) CH2Cl2, -30 deg C, 1.5 h; 2.) 1 h 6: 0.035 g / pyridine View Scheme

butanoic acid anhydride (106-31-0) + Anecortave (10184-70-0) → 17α,21-dibutanoyloxy-pregna-4,9(11)-diene-3,20-dione (496942-70-2)

Conditions	Yield
With toluene-4-sulfonic acid In various solvent(s)

Anecortave (10184-70-0) → C21H30O4 + 17,21-dihydroxy-5α-pregn-9(11)-ene-3,20-dione

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 5%-palladium/activated carbon In ethanol for 6h; Reagent/catalyst; Reflux; Overall yield = 73 %; stereoselective reaction;	A n/a B n/a

Anecortave (10184-70-0) → (5β)-androst-9(11)-ene-3,17-dione (1093397-63-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 5%-palladium/activated carbon / ethanol / 6 h / Reflux 2: dipyridinium dichromate / dichloromethane / 48 h / 25 °C View Scheme

Anecortave (10184-70-0) → 17α-octadecanoyloxy-21-hydroxy-pregna-4,9(11)-diene-3,20-dione

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 2: Bacillus subtilis protease / tetrahydrofuran / 48 h / 45 °C / Enzymatic reaction 3: triphenylphosphine / dichloromethane / 0.5 h / 20 °C View Scheme

Anecortave (10184-70-0) → 17α-octadecanoyloxy-21-butanoyloxy-pregna-4,9(11)-diene-3,20-dione

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 2: Bacillus subtilis protease / tetrahydrofuran / 48 h / 45 °C / Enzymatic reaction 3: triphenylphosphine / dichloromethane / 0.5 h / 20 °C 4: methyl tributylammonium chloride / 2 h / 20 °C View Scheme

Anecortave (10184-70-0) → 17α-octadecanoyloxy-21-allylcarbonyloxy-pregna-4,9(11)-diene-3,20-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 2: Bacillus subtilis protease / tetrahydrofuran / 48 h / 45 °C / Enzymatic reaction View Scheme

Anecortave (10184-70-0) + Allyl chloroformate (2937-50-0) → 17α-hydroxy-21-allylcarbonyloxy-pregna-4,9(11)-diene-3,20-dione

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 0.5h;

Upstream product

• 7753-60-8 anecortave 
• 428516-04-5 21-acetoxy-3,3;20,20-bis-ethanediyldioxy-pregna-5,9⁽¹¹⁾-dien-17-ol 
• 119669-94-2 Nicotinic acid (8S,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 
• 108674-98-2 Nicotinic acid (8S,9R,10S,13S,14S,17R)-17-(2-acetoxy-acetyl)-9-chloro-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 
• 566-35-8 Epicortisol 
• 113862-93-4 21-acetoxy-17-hydroxy-11α-methanesulfonyloxy-pregn-4-ene-3,20-dione 
• 74220-42-1 21-acetoxy-3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17-diol 
• 76338-54-0 3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17,21-triol 

Downstream Products

• 7753-60-8 anecortave 
• 1035-69-4 androst-4,9⁽¹¹⁾-dien-3,17-dione 
• 2398-99-4 hydroxy-17β androstadiene-4,9(11) one-3,7 

Relevant articles and documents

Microbial conversion of pregna-4,9(11)-diene-17α,21-diol-3,20-dione acetates by Nocardioides simplex VKM Ac-2033D

The conversion of pregna-4,9(11)-diene-17α,21-diol-3,20-dione 21-acetate (I) and 17,21-diacetate (VI) by Nocardioides simplex VKM Ac-2033D was studied. The major metabolites formed from I were identified as pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (II) and pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione (IV). Pregna-4,9(11)-diene-17α,21-diol-3,20-dione (III) and pregna-1,4,9(11)-triene-17α,20β,21-triol-3-one (V) were formed in minorities. Biotransformation products formed from VI were pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 17,21-diacetate (VII), pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (II), pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione (IV), pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 17-acetate (VIII), pregna-1,4,9(11)-triene-17α,20β,21-triol-3-one (V). The conversion pathways were proposed including 1(2)-dehydrogenation, deacetylation, 20β-reduction and non-enzymatic migration of acyl group from position 17 to 21. The conditions providing predominant accumulation of pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (II) from I and pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 17-acetate (VIII) from VI in a short-term biotransformation were determined.

Selective Steroid Chlorinations Directed by Attached Pyridine Ester Templates

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Non-hormonal steroid modulators of NF-κβ for treatment of disease

The present invention relates to compounds and methods which may be useful as treatments of diseases.

17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one

The invention is the compound 17β-cyano-9α, 17α-dihydroxyandrost-4-en-3-one (I) which is particularly useful as an intermediate in the production of the 17α-halo silyl ethers (II).