11-Ketoprogesterone supplier

Name
11-Ketoprogesterone
EINECS 208-222-1
CAS No. 516-15-4
Article Data43
CAS DataBase
Density 1.14 g/cm³
Solubility
Melting Point 170-175 °C (lit.)
Formula C₂₁H₂₈O₃
Boiling Point 487.6 °C at 760 mmHg
Molecular Weight 328.452
Flash Point 209.3 °C
Transport Information
Appearance white crystalline
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 11-Oxopregn-4-ene-3,20-dione;11-Oxoprogesterone;DG 322A;Ketogestin;Ketoprogesterone;
PSA 51.21000
LogP 3.90250

Synthetic route

: 80-75-1
11-alpha-hydroxyprogesterone

: 516-15-4
11-Ketoprogesterone

Conditions

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

: 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

: 516-15-4
11-Ketoprogesterone

Conditions

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

: 53-06-5
Cortisone

A: 516-15-4
11-Ketoprogesterone

B: 72-23-1
11-dehydrocorticosterone

Conditions

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%

: 129786-19-2
21-Methoxypregn-4-ene-3,11,20-trione

A: 516-15-4
11-Ketoprogesterone

B: 72-23-1
11-dehydrocorticosterone

Conditions

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

: 129786-20-5
21-(Trityloxy)pregn-4-ene-3,11,20-trione

A: 516-15-4
11-Ketoprogesterone

B: 72-23-1
11-dehydrocorticosterone

Conditions

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

: 974-84-5
11β-fluoropregn-4-ene-3,20-dione

: 516-15-4
11-Ketoprogesterone

Conditions

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

: 565-96-8
11α-hydroxy-5β-pregnane-3,20-dione

: 516-15-4
11-Ketoprogesterone

Conditions

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

: 3β-acetoxy-9,11α-epoxy-5-hydroxy-5α-pregn-7-en-20-one

: 516-15-4
11-Ketoprogesterone

Conditions

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

4ξ-bromo-5β-pregnanetrione-(3.11.20): 4ξ-bromo-5β-pregnanetrione-(3.11.20)

: 516-15-4
11-Ketoprogesterone

Conditions

Conditions	Yield
With pyridine

strychnine salt of/the/ 3,3-ethanediyldioxy-11,20,23-trioxo-21-nor-chol-5-en-24-oic acid: strychnine salt of/the/ 3,3-ethanediyldioxy-11,20,23-trioxo-21-nor-chol-5-en-24-oic acid

: 516-15-4
11-Ketoprogesterone

Conditions

Conditions	Yield
Hydrolysis;

: 4031-30-5
9α-bromo-11β-fluoropregn-4-ene-3,20-dione

: 516-15-4
11-Ketoprogesterone

Conditions

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

: 72-23-1
11-dehydrocorticosterone

: 516-15-4
11-Ketoprogesterone

Conditions

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

: 129786-20-5
21-(Trityloxy)pregn-4-ene-3,11,20-trione

: 516-15-4
11-Ketoprogesterone

Conditions

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

: 516-15-4
11-Ketoprogesterone

: 108-24-7
acetic anhydride

: 38368-22-8
(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

Conditions

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%

: 516-15-4
11-Ketoprogesterone

: 2089-06-7
5α-pregnane-3,11,20-trione

Conditions

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;

: 516-15-4
11-Ketoprogesterone

: 108-24-7
acetic anhydride

: 107-21-1
ethylene glycol

: 55105-52-7
(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

Conditions

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%

...Expand

: 516-15-4
11-Ketoprogesterone

: 3-((3S,3aS,5aS,6R,9aS,9bS)-3-Acetyl-3a,6-dimethyl-5,7-dioxo-dodecahydro-cyclopenta[a]naphthalen-6-yl)-propionic acid

Conditions

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%

: 516-15-4
11-Ketoprogesterone

: 4368-11-0
Pregn-1,4-diene-3,11,20-trione

Conditions

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

: 516-15-4
11-Ketoprogesterone

A: 4368-11-0
Pregn-1,4-diene-3,11,20-trione

B: (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

C: 78261-67-3
17α-hydroxy-11-oxoandrosta-1,4-dien-3-one-17β-carboxylic acid

Conditions

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

...Expand

: 516-15-4
11-Ketoprogesterone

: (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

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

: 123-75-1
pyrrolidine

: 516-15-4
11-Ketoprogesterone

: 38196-65-5
3-pyrrolidino-pregna-3,5-diene-11,20-dione

Conditions

Conditions	Yield
With benzene

: 110-91-8
morpholine

: 516-15-4
11-Ketoprogesterone

: 3-morpholino-pregna-3,5-diene-11,20-dione

Conditions

Conditions	Yield

11-Ketoprogesterone Specification

The 11-Ketoprogesterone, with the CAS registry number of 516-15-4, is also known as Pregn-4-ene-3, 11, 20-trione. It belongs to the product categories of Biochemistry; Steroids; Steroids (Others). Its EINECS registry number is 208-222-1. This chemical's molecular formula is C₂₁H₂₈O₃ and molecular weight is 328.45. What's more, its IUPAC name is (8S, 9S, 10R, 13S, 14S, 17S)-17-Acetyl-10, 13-dimethyl-2, 6, 7, 8, 9, 12, 14, 15, 16, 17-decahydro-1H-cyclopenta[a]phenanthrene-3, 11-dione. This chemical's classification codes are Hormone; Mutation Data; Reproductive Effect. In addition, it must be stored in airtight containers and placed in a dry, cool, well-ventilated place. Meanwhile, it should be avoided contact with light, ignition source, heat source, oxidant. And it can not be stored together with acids, edible chemicals.

Physical properties about 11-Ketoprogesterone are: (1)ACD/LogP: 2.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.36; (4)ACD/LogD (pH 7.4): 2.36; (5)ACD/BCF (pH 5.5): 36.6; (6)ACD/BCF (pH 7.4): 36.6; (7)ACD/KOC (pH 5.5): 457.87; (8)ACD/KOC (pH 7.4): 457.87; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 51.21 Å²; (13)Index of Refraction: 1.55; (14)Molar Refractivity: 91.07 cm³; (15)Molar Volume: 285.8 cm³; (16)Surface Tension: 44.2 dyne/cm; (17)Density: 1.14 g/cm³; (18)Flash Point: 209.3 °C; (19)Enthalpy of Vaporization: 75.35 kJ/mol; (20)Boiling Point: 487.6 °C at 760 mmHg; (21)Vapour Pressure: 1.17E-09 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(C)[C@H]3CC[C@H]2[C@@H]4CC\C1=C\C(=O)CC[C@]1(C)[C@H]4C(=O)C[C@@]23C
(2) 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
(3) InChIKey: WKAVAGKRWFGIEA-DADBAOPHBO

Product Name

11-Ketoprogesterone

Synthetic route

11-Ketoprogesterone Specification

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