516-15-4

Basic information

• Product Name: 11-KETOPROGESTERONE
• Synonyms: 11-oxoprogesterone;ketogestin;ketoprogesterone;u1258;PREGN-4-ENE-3,11,20-TRIONE;11-KETOPROGESTERONE;4-PREGNENE-3,11,20-TRIONE;4-PREGNEN-3,11,20-TRIONE
• CAS NO: 516-15-4
• Molecular Formula: C₂₁H₂₈O₃
• Molecular Weight: 328.45
• EINECS: 208-222-1
• Product Categories: Biochemistry;Steroids;Steroids (Others)
• Mol File: 516-15-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 170-175 °C(lit.)
• Boiling Point: 487.6 °C at 760 mmHg
• Flash Point: 209.3 °C
• Appearance: white/crystalline
• Density: 1.14 g/cm³
• Vapor Pressure: 1.17E-09mmHg at 25°C
• Refractive Index: 1.55
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 11-KETOPROGESTERONE(CAS DataBase Reference)
• NIST Chemistry Reference: 11-KETOPROGESTERONE(516-15-4)
• EPA Substance Registry System: 11-KETOPROGESTERONE(516-15-4)

Safety Data

• RTECS: TU5513000
• Hazardous Substances Data: 516-15-4(Hazardous Substances Data)

Usage

Uses

11-Ketoprogesterone is a metabolite of Progesterone which is a steroid hormone Inducing maturation and secretory activity of the uterine endothelium. Progesterone is implicated in the etiology of breast cancer.

InChI:InChI=1/C21H28O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-17,19H,4-9,11H2,1-3H3/t15-,16+,17-,19+,20-,21+/m0/s1

Synthetic route

11-alpha-hydroxyprogesterone (80-75-1) → 11-Ketoprogesterone (516-15-4)

Conditions	Yield
With chromium(VI) oxide In water; acetic acid for 1.5h;	90%
With chromium(VI) oxide; acetic acid In water at 20℃; for 1.5h;	90%
With chromium(VI) oxide; acetic acid

(8S,9S,10R,11S,13S,14S,17S)-17-Acetyl-11-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (600-57-7) → 11-Ketoprogesterone (516-15-4)

Conditions	Yield
for 35h; incubation with Rhizopus stolonifer ATCC 6227b;	85%
With chromium(VI) oxide; acetic acid

Cortisone (53-06-5) → 11-Ketoprogesterone (516-15-4) + 11-dehydrocorticosterone (72-23-1)

Conditions	Yield
With trimethylsilyl iodide In chloroform for 3h; Ambient temperature;	A 84% B 10%
With trimethylsilyl iodide In chloroform for 2h; Ambient temperature;	A 84% B 10%
With trimethylsilyl iodide In acetonitrile for 3h; Ambient temperature;	A 27% B 46%
With trimethylsilyl iodide In acetonitrile for 3h; Ambient temperature;	A 27% B 46%

21-Methoxypregn-4-ene-3,11,20-trione (129786-19-2) → 11-Ketoprogesterone (516-15-4) + 11-dehydrocorticosterone (72-23-1)

Conditions	Yield
With methanol; trimethylsilyl iodide In acetonitrile for 10h; Ambient temperature;	A 72% B 4%

21-(Trityloxy)pregn-4-ene-3,11,20-trione (129786-20-5) → 11-Ketoprogesterone (516-15-4) + 11-dehydrocorticosterone (72-23-1)

Conditions	Yield
With methanol; trimethylsilyl iodide In acetonitrile for 2.5h; Ambient temperature;	A 55% B 7%

11β-fluoropregn-4-ene-3,20-dione (974-84-5) → 11-Ketoprogesterone (516-15-4)

Conditions	Yield
for 36h; incubation with Rhizopus stolonifer ATCC 6227b;	33%

11α-hydroxy-5β-pregnane-3,20-dione (565-96-8) → 11-Ketoprogesterone (516-15-4)

Conditions	Yield
ueber 2α-Brom-5α-pregnan-3,11,20-trion;

3β-acetoxy-9,11α-epoxy-5-hydroxy-5α-pregn-7-en-20-one → 11-Ketoprogesterone (516-15-4)

Conditions	Yield
ueber 3β-Acetoxy-5-hydroxy-5α-pregnan-11,20-dion;

4ξ-bromo-5β-pregnanetrione-(3.11.20) → 11-Ketoprogesterone (516-15-4)

Conditions	Yield
With pyridine

strychnine salt of/the/ 3,3-ethanediyldioxy-11,20,23-trioxo-21-nor-chol-5-en-24-oic acid → 11-Ketoprogesterone (516-15-4)

Conditions	Yield
Hydrolysis;

9α-bromo-11β-fluoropregn-4-ene-3,20-dione (4031-30-5) → 11-Ketoprogesterone (516-15-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / tri-n-butyltin hydride, azoisobutironitrile / tetrahydrofuran / 5 h / Ambient temperature 2: 33 percent / 36 h / incubation with Rhizopus stolonifer ATCC 6227b View Scheme

11-dehydrocorticosterone (72-23-1) → 11-Ketoprogesterone (516-15-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 16 percent / pyridine / 216 h / Ambient temperature 2: 55 percent / Me3SiI, MeOH / acetonitrile / 2.5 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 77 percent / Ag2O / 12 h / Heating 2: 72 percent / Me3SiI, MeOH / acetonitrile / 10 h / Ambient temperature View Scheme

21-(Trityloxy)pregn-4-ene-3,11,20-trione (129786-20-5) → 11-Ketoprogesterone (516-15-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 7 percent / Me3SiI, MeOH / acetonitrile / 2.5 h / Ambient temperature 2: 77 percent / Ag2O / 12 h / Heating 3: 72 percent / Me3SiI, MeOH / acetonitrile / 10 h / Ambient temperature View Scheme

11-Ketoprogesterone (516-15-4) + acetic anhydride (108-24-7) → (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-11-oxo-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate (38368-22-8)

Conditions	Yield
With perchloric acid In ethyl acetate at 20℃; for 0.333333h;	89%
With perchloric acid In ethyl acetate for 0.333333h; Ambient temperature;	85%

11-Ketoprogesterone (516-15-4) → 5α-pregnane-3,11,20-trione (2089-06-7)

Conditions	Yield
With ammonia; lithium In tert-butyl alcohol at -78℃; for 2h;	78%
With potato dextrose broth medium In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436;	40%
With hydrogen; palladium on activated charcoal
With jones reagent; ammonia; lithium 1.) THF, 2.) acetone, 5 min; Yield given. Multistep reaction;

11-Ketoprogesterone (516-15-4) + acetic anhydride (108-24-7) + ethylene glycol (107-21-1) → (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-11-oxo-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate (55105-52-7)

Conditions	Yield
Stage #1: 11-Ketoprogesterone; acetic anhydride With formic acid In ethyl acetate for 0.116667h; Stage #2: With pyridine In methanol Stage #3: ethylene glycol With toluene-4-sulfonic acid In benzene for 2h; Reflux;	66%

11-Ketoprogesterone (516-15-4) → 3-((3S,3aS,5aS,6R,9aS,9bS)-3-Acetyl-3a,6-dimethyl-5,7-dioxo-dodecahydro-cyclopenta[a]naphthalen-6-yl)-propionic acid

Conditions	Yield
Stage #1: 11-Ketoprogesterone With sodium carbonate In water; tert-butyl alcohol Reflux; Stage #2: With potassium permanganate; sodium periodate In water; tert-butyl alcohol for 3h; Reflux;	56%
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile for 0.75h;	16%

11-Ketoprogesterone (516-15-4) → Pregn-1,4-diene-3,11,20-trione (4368-11-0)

Conditions	Yield
With diphenyl diselenide; iodosylbenzene In benzene for 12h; Heating;	51%
With tert-butyldimethylsilyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 0 - 40℃; for 20h;	45%
With septomyxa affinin

11-Ketoprogesterone (516-15-4) → Pregn-1,4-diene-3,11,20-trione (4368-11-0) + (8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid + 17α-hydroxy-11-oxoandrosta-1,4-dien-3-one-17β-carboxylic acid (78261-67-3)

Conditions	Yield
With iodoxybenzene; benzeneseleninic anhydride In benzene for 12h; Heating;	A 51% B n/a C n/a

11-Ketoprogesterone (516-15-4) → (10R,11S,13S,17S)-11-hydroxy-17-(2-hydroxypropane-2-yl)-10,13-dimethyl-1,2,6,7,8, 9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a] phenanthrene-3-one

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; ethanol; water at 0℃;	35%

pyrrolidine (123-75-1) + 11-Ketoprogesterone (516-15-4) → 3-pyrrolidino-pregna-3,5-diene-11,20-dione (38196-65-5)

Conditions	Yield
With benzene

morpholine (110-91-8) + 11-Ketoprogesterone (516-15-4) → 3-morpholino-pregna-3,5-diene-11,20-dione

Conditions	Yield

Upstream product

• 124319-59-1 rac-3,3-ethanediyldioxy-11,20-dioxo-16,17-seco-13α-pregn-5-en-16-oic acid methyl ester 
• 114447-53-9 rac-3,3-ethanediyldioxy-13α,17ξH-pregn-5-ene-11,16,20-trione 
• 119657-91-9 rac-3,3-ethanediyldioxy-16-(toluene-4-sulfonyloxy)-13α-pregna-5,16-diene-11,20-dione 
• 5716-98-3 rac-3,3-ethanediyldioxy-13α,17ξH-pregn-5-ene-11,20-dione 
• 124319-59-1 rac-3,3-ethanediyldioxy-11,20-dioxo-16,17-seco-14β-pregn-5-en-16-oic acid methyl ester 
• 114447-53-9 rac-3,3-ethanediyldioxy-14β,17ξH-pregn-5-ene-11,16,20-trione 
• 119657-91-9 rac-3,3-ethanediyldioxy-16-(toluene-4-sulfonyloxy)-14β-pregna-5,16-diene-11,20-dione 
• 5716-98-3 rac-3,3-ethanediyldioxy-14β,17ξH-pregn-5-ene-11,20-dione 
• 22847-91-2 11-α-hydroxyprogesterone 
• 50-22-6 Corticosterone 
• 57-83-0 progesterone 
• 129786-20-5 21-(Trityloxy)pregn-4-ene-3,11,20-trione 
• 72-23-1 11-dehydrocorticosterone 
• 4031-30-5 9α-bromo-11β-fluoropregn-4-ene-3,20-dione 

Downstream Products

• 565-99-1 UC₁₀₁₇ 
• 21063-91-2 3,11,20-Trioxo-pregnadien-4,6 
• 72-23-1 11-dehydrocorticosterone 
• 4368-11-0 1-dehydro-11-oxoprogesterone 
• 28449-15-2 6β-hydroxypregn-4-ene-3,11,20-trione 
• 1164-86-9 1-((3S,8S,9S,10R,11S,13S,14S,17S)-3,11-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-yl)ethan-1-one 
• 23930-19-0 Alphaxalone 
• 1173-27-9 21-acetoxy-pregn-4-ene-3,11,20-trione 
• 1913-28-6 11,19-Oxidopregn-4-ene-3,20-dione 
• 600-57-7 (8S,9S,10R,11S,13S,14S,17S)-17-Acetyl-11-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 
• 3676-17-3 5α-pregnane-3β,11β,20-triol 
• 77943-98-7 (8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-17-((R)-1-hydroxyethyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthrene-3-one 
• 80699-76-9 (8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid 
• 78261-67-3 17α-hydroxy-11-oxoandrosta-1,4-dien-3-one-17β-carboxylic acid 

Relevant articles and documents

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