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

Description

11-Ketoprogesterone, a metabolite of the steroid hormone Progesterone, plays a significant role in the reproductive system. It is involved in inducing the maturation and secretory activity of the uterine endothelium, which is crucial for the proper functioning of the female reproductive system. Additionally, Progesterone has been implicated in the etiology of breast cancer, making 11-Ketoprogesterone a compound of interest in the field of reproductive health and oncology.

Uses

Used in Reproductive Health:
11-Ketoprogesterone is used as a hormone regulator for maintaining the health and function of the female reproductive system. It is essential for the maturation and secretory activity of the uterine endothelium, which is vital for successful implantation and pregnancy.
Used in Oncology:
11-Ketoprogesterone is used as a research compound in the study of breast cancer etiology. Its connection to Progesterone, a hormone implicated in the development of breast cancer, makes it a valuable tool for understanding the underlying mechanisms and potential therapeutic targets for this type of cancer.
Used in Drug Development:
11-Ketoprogesterone can be used as a starting material or a target for the development of new drugs aimed at treating reproductive disorders and breast cancer. Its role in the reproductive system and its association with cancer make it a promising candidate for the development of novel therapeutic agents.

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

• 565-96-8 11α-hydroxy-5β-pregnane-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 
• 80-75-1 11-alpha-hydroxyprogesterone 
• 53-06-5 Cortisone 
• 129786-19-2 21-Methoxypregn-4-ene-3,11,20-trione 
• 129786-20-5 21-(Trityloxy)pregn-4-ene-3,11,20-trione 
• 72-23-1 11-dehydrocorticosterone 
• 5716-98-3 rac-3,3-ethanediyldioxy-14β,17ξH-pregn-5-ene-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-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 
• 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 

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 
• 1173-27-9 21-acetoxy-pregn-4-ene-3,11,20-trione 
• 2089-06-7 5α-pregnane-3,11,20-trione 
• 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 
• 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 
• 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 
• 1913-28-6 11,19-Oxidopregn-4-ene-3,20-dione 

Relevant articles and documents

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