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  • 640-87-9 Structure
  • Basic information

    1. Product Name: REICHSTEIN'S SUBSTANCE S 21-ACETATE
    2. Synonyms: 17α,21-Dihydroxyprogesterone 21-acetate;17α-Hydroxycortexone 21-acetate;4-Pregnene-17α,21-diol-3,20-dione 21-acetate;RSA,REICHSTEIN'S SUBSTANCE S 21-ACETATE;17a-Hydroxy Progesterone-21-Acetate(RSA);REICHSTEIN'S COMPOUND ''S'' ACETATE;REICHSTEIN'S SUBSTANCE S 21-ACETATE;17,21-Dihydroxypregn-4-ene-3,20-dione21-acetate
    3. CAS NO:640-87-9
    4. Molecular Formula: C23H32O5
    5. Molecular Weight: 388.5
    6. EINECS: 211-369-4
    7. Product Categories: Steroids;Intermediates & Fine Chemicals;Pharmaceuticals
    8. Mol File: 640-87-9.mol
    9. Article Data: 19
  • Chemical Properties

    1. Melting Point: 233-235°C
    2. Boiling Point: 537.9±50.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.4 g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: Refrigerator
    8. Solubility: Chloroform (Sparingly), Methanol (Slightly, Heated)
    9. PKA: 12.59±0.60(Predicted)
    10. CAS DataBase Reference: REICHSTEIN'S SUBSTANCE S 21-ACETATE(CAS DataBase Reference)
    11. NIST Chemistry Reference: REICHSTEIN'S SUBSTANCE S 21-ACETATE(640-87-9)
    12. EPA Substance Registry System: REICHSTEIN'S SUBSTANCE S 21-ACETATE(640-87-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 640-87-9(Hazardous Substances Data)

640-87-9 Usage

Description

REICHSTEIN'S SUBSTANCE S 21-ACETATE, also known as 17α-Hydroxy-11-deoxycorticosterone-21-acetate (Hydrocortisone EP Impurity K), is a synthetic steroid acetate substance 'S' that functions as a carbaryl synergist. It is a derivative of the naturally occurring hormone cortisol, with an acetate group attached to the 21st carbon atom, which enhances its lipophilic properties and allows for better absorption and distribution in the body.

Uses

Used in Pesticide Industry:
REICHSTEIN'S SUBSTANCE S 21-ACETATE is used as a carbaryl synergist for enhancing the effectiveness of carbaryl-based insecticides. As a synthetic steroid, it works by interfering with the endocrine system of insects, making them more susceptible to the toxic effects of carbaryl. This results in improved pest control and reduced chemical usage, leading to more sustainable and environmentally friendly agricultural practices.
Used in Pharmaceutical Industry:
REICHSTEIN'S SUBSTANCE S 21-ACETATE is used as an intermediate in the synthesis of various corticosteroid drugs. Corticosteroids are a class of steroid hormones that have potent anti-inflammatory and immunosuppressive properties. They are widely used in the treatment of various medical conditions, such as allergies, asthma, arthritis, and autoimmune diseases. By serving as a key intermediate in the production of these drugs, REICHSTEIN'S SUBSTANCE S 21-ACETATE plays a crucial role in the development and manufacturing of life-saving medications.
Used in Research and Development:
REICHSTEIN'S SUBSTANCE S 21-ACETATE is also used as a research tool in the study of steroid hormones and their effects on various biological processes. It can be employed in laboratory experiments to investigate the mechanisms of action, metabolism, and pharmacokinetics of corticosteroids. Additionally, it can be used to develop new synthetic steroids with improved therapeutic properties or novel applications in various fields, such as medicine, agriculture, and environmental management.

Check Digit Verification of cas no

The CAS Registry Mumber 640-87-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 0 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 640-87:
(5*6)+(4*4)+(3*0)+(2*8)+(1*7)=69
69 % 10 = 9
So 640-87-9 is a valid CAS Registry Number.

640-87-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name REICHSTEIN'S SUBSTANCE S 21-ACETATE

1.2 Other means of identification

Product number -
Other names CORTEXOLONE ACETATE

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:640-87-9 SDS

640-87-9Synthetic route

Cortexolone
152-58-9

Cortexolone

acetic anhydride
108-24-7

acetic anhydride

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With pyridine at 20℃; for 0.5h;100%
With pyridine
17-hydroxyprogesterone
68-96-2

17-hydroxyprogesterone

acetic anhydride
108-24-7

acetic anhydride

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Stage #1: 17-hydroxyprogesterone With calcium chloride; calcium oxide In methanol; chloroform for 2h;
Stage #2: acetic anhydride With potassium carbonate; acetic acid In methanol; chloroform; N,N-dimethyl-formamide at 100℃; for 1h;
98%
17-hydroxyprogesterone
68-96-2

17-hydroxyprogesterone

potassium acetate
127-08-2

potassium acetate

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Stage #1: 17-hydroxyprogesterone With pyrrolidine In ethanol at 0 - 50℃;
Stage #2: potassium acetate With acetic acid; potassium iodide In ethanol; acetone at 20 - 60℃;
98%
21-Iodo-17α-hydroxypregn-4-en-3,20-dione
4470-79-5

21-Iodo-17α-hydroxypregn-4-en-3,20-dione

acetic acid
64-19-7

acetic acid

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With triethylamine In acetone for 5h; Heating; Inert atmosphere;97%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

Cortexolone
152-58-9

Cortexolone

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With Rhizopus oryzae lipase immobilized on Lewatit 1600 resin In di-isopropyl ether at 55℃; for 48h; regioselective reaction;91%
17α-hydroxy-21-chloro-4-pregnene-3,20-dione
20380-16-9

17α-hydroxy-21-chloro-4-pregnene-3,20-dione

potassium acetate
127-08-2

potassium acetate

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 0.5h;90%
21-bromo-17α-hydroxy-4-pregnene-3,20-dione
20380-17-0

21-bromo-17α-hydroxy-4-pregnene-3,20-dione

potassium acetate
127-08-2

potassium acetate

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
In acetone at 50℃; for 1h;86%
Yield given;
3β,17α,21-trihydroxypregn-5-en-20-one 21-acetate
1474-10-8

3β,17α,21-trihydroxypregn-5-en-20-one 21-acetate

A

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

B

Acetic acid 2-((8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester

Acetic acid 2-((8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester

Conditions
ConditionsYield
With <(C4Ph4COHOCC4Ph4)(μ-H)><(CO)4Ru2>; acetone at 56℃; for 24h;A 67%
B 28%
17α,21-dihydroxy-4-pregnene-3,20-dione 17-acetate
19357-45-0

17α,21-dihydroxy-4-pregnene-3,20-dione 17-acetate

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With potassium acetate In N,N-dimethyl-formamide at 105℃; for 6h;51%
21-acetoxy-20-cyanopregna-4,17(20)-dien-3-one
88261-15-8

21-acetoxy-20-cyanopregna-4,17(20)-dien-3-one

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane Ambient temperature;28%
17.20βF-dihydroxy-21-acetoxy-pregnen-(4)-one-(3)
39703-74-7

17.20βF-dihydroxy-21-acetoxy-pregnen-(4)-one-(3)

A

Androstenedione
63-05-8

Androstenedione

B

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With chromium(VI) oxide; water; acetic acid at 11℃;
4β-bromo-17-hydroxy-21-acetoxy-5β-pregnanedione-(3.20)
96263-55-7

4β-bromo-17-hydroxy-21-acetoxy-5β-pregnanedione-(3.20)

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With semicarbazide hydrochloride; sodium acetate; acetic acid Erwaermen des Reaktionsgemisches mit Brenztraubensaeure und Natriumacetat unter Zusatz von Wasser;
With sodium acetate; acetic acid; (2,4-dinitro-phenyl)-hydrazine Erwaermen des Reaktionsgemisches mit Brenztraubensaeure unter Zusatz von Chloroform und Wasser;
21-acetoxy-5,6β-dichloro-17-hydroxy-5α-pregnane-3,20-dione
113651-23-3

21-acetoxy-5,6β-dichloro-17-hydroxy-5α-pregnane-3,20-dione

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With chromium dichloride
4β-bromo-17-hydroxy-21-acetoxy-5β-pregnanedione-(3.20)
96263-55-7

4β-bromo-17-hydroxy-21-acetoxy-5β-pregnanedione-(3.20)

semicarbazide hydrochloride
563-41-7

semicarbazide hydrochloride

sodium acetate
127-09-3

sodium acetate

acetic acid
64-19-7

acetic acid

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
anschliessend mit Brenztraubensaeure, Natriumacetat und Wasser;
4β-bromo-17-hydroxy-21-acetoxy-5β-pregnanedione-(3.20)
96263-55-7

4β-bromo-17-hydroxy-21-acetoxy-5β-pregnanedione-(3.20)

sodium acetate
127-09-3

sodium acetate

acetic acid
64-19-7

acetic acid

(2,4-dinitro-phenyl)-hydrazine
119-26-6

(2,4-dinitro-phenyl)-hydrazine

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
anschliessend mit Chloroform, Brenztraubensaeure und Wasser;
potassium acetate
127-08-2

potassium acetate

17α-hydroxy-3-(N-morpholinyl)pregna-3,5-dien-20-one
132950-03-9

17α-hydroxy-3-(N-morpholinyl)pregna-3,5-dien-20-one

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Yield given. Multistep reaction;
17α-21-dihydroxy-5-α-pregnane-3,20-dione
312-99-2

17α-21-dihydroxy-5-α-pregnane-3,20-dione

acetic anhydride
108-24-7

acetic anhydride

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Multistep reaction;
17α-acetoxy-21-chloro-4-pregnene-3,20-dione
57273-80-0

17α-acetoxy-21-chloro-4-pregnene-3,20-dione

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With potassium acetate In N,N-dimethyl-formamide at 105℃; for 5h;
21-acetoxy-16α.17-epoxy-pregnene-(4)-dione-(3.20)

21-acetoxy-16α.17-epoxy-pregnene-(4)-dione-(3.20)

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
With hydrogen bromide; acetic acid Erwaermen des Reaktionsprodukts mit Aethanol und Raney-Nickel;
17.20βF-dihydroxy-21-acetoxy-pregnen-(4)-one-(3)
39703-74-7

17.20βF-dihydroxy-21-acetoxy-pregnen-(4)-one-(3)

water
7732-18-5

water

acetic acid
64-19-7

acetic acid

CrO3

CrO3

A

Androstenedione
63-05-8

Androstenedione

B

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

methyl 20-cyano-3β-hydroxypregna-5,17(20)-dien-21-oate
88261-10-3

methyl 20-cyano-3β-hydroxypregna-5,17(20)-dien-21-oate

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 92 percent / p-TsOH / CH2Cl2 / 1.5 h / Ambient temperature
2: 67 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -78 °C
3: 83 percent / pyridine / Ambient temperature
4: 95 percent / p-TsOH, MeOH / 0.05 h / 50 °C
5: 77 percent / aluminium isopropoxide / toluene; cyclohexanone / 20 h / Heating
6: 28 percent / KMnO4, triethylbenzylammonium chloride (TEBACl) / CH2Cl2 / Ambient temperature
View Scheme
20-cyanopregna-5,17(20)-diene-3β,21-diol 21-acetate
88261-14-7

20-cyanopregna-5,17(20)-diene-3β,21-diol 21-acetate

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 77 percent / aluminium isopropoxide / toluene; cyclohexanone / 20 h / Heating
2: 28 percent / KMnO4, triethylbenzylammonium chloride (TEBACl) / CH2Cl2 / Ambient temperature
View Scheme
20-cyano-3β-tetrahydropyranyloxypregna-5,17(20)-dien-21-ol
88261-12-5

20-cyano-3β-tetrahydropyranyloxypregna-5,17(20)-dien-21-ol

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 83 percent / pyridine / Ambient temperature
2: 95 percent / p-TsOH, MeOH / 0.05 h / 50 °C
3: 77 percent / aluminium isopropoxide / toluene; cyclohexanone / 20 h / Heating
4: 28 percent / KMnO4, triethylbenzylammonium chloride (TEBACl) / CH2Cl2 / Ambient temperature
View Scheme
[(3S,8R,9S,10R,13S,14S)-3-Acetoxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-cyano-acetic acid ethyl ester

[(3S,8R,9S,10R,13S,14S)-3-Acetoxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-cyano-acetic acid ethyl ester

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: KOH / H2O; tetrahydrofuran / 4 h
2: 92 percent / p-TsOH / CH2Cl2 / 1.5 h / Ambient temperature
3: 67 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -78 °C
4: 83 percent / pyridine / Ambient temperature
5: 95 percent / p-TsOH, MeOH / 0.05 h / 50 °C
6: 77 percent / aluminium isopropoxide / toluene; cyclohexanone / 20 h / Heating
7: 28 percent / KMnO4, triethylbenzylammonium chloride (TEBACl) / CH2Cl2 / Ambient temperature
View Scheme
methyl 20-cyano-3β-tetrahydropyranyloxypregna-5,17(20)-dien-21-oate
88261-11-4

methyl 20-cyano-3β-tetrahydropyranyloxypregna-5,17(20)-dien-21-oate

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 67 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -78 °C
2: 83 percent / pyridine / Ambient temperature
3: 95 percent / p-TsOH, MeOH / 0.05 h / 50 °C
4: 77 percent / aluminium isopropoxide / toluene; cyclohexanone / 20 h / Heating
5: 28 percent / KMnO4, triethylbenzylammonium chloride (TEBACl) / CH2Cl2 / Ambient temperature
View Scheme
20-cyano-3β-tetrahydropyranyloxypregna-5,17(20)-dien-21-ol acetate
88261-13-6

20-cyano-3β-tetrahydropyranyloxypregna-5,17(20)-dien-21-ol acetate

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / p-TsOH, MeOH / 0.05 h / 50 °C
2: 77 percent / aluminium isopropoxide / toluene; cyclohexanone / 20 h / Heating
3: 28 percent / KMnO4, triethylbenzylammonium chloride (TEBACl) / CH2Cl2 / Ambient temperature
View Scheme
21-Brom-17-(formyloxy)-4-pregnen-3,20-dion
80134-08-3

21-Brom-17-(formyloxy)-4-pregnen-3,20-dion

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. KHCO3 / methanol
View Scheme
Multi-step reaction with 2 steps
1: 86 percent / KHCO3 / methanol; H2O / 0.5 h / Ambient temperature
2: 86 percent / acetone / 1 h / 50 °C
View Scheme
Epiandrosterone
481-29-8

Epiandrosterone

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
2: (N,N-dimethylamino)pyridine, pyridine
3: 92 percent / PdCl2(CH3CN)2 / tetrahydrofuran / Ambient temperature
4: 1. KOH, 2.) N-bromoacetamide
View Scheme
3β,21-Diacetoxy-5α-pregn-17-ene
74499-15-3

3β,21-Diacetoxy-5α-pregn-17-ene

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1. KOH, 2.) N-bromoacetamide
View Scheme
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

ethylene glycol
107-21-1

ethylene glycol

21-acetoxy-17α-hydroxy-3,3-ethylenedioxypregn-5-ene-20-one
913-44-0

21-acetoxy-17α-hydroxy-3,3-ethylenedioxypregn-5-ene-20-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid; formic acid ethyl ester at 60℃; for 3h;86%
With toluene-4-sulfonic acid; benzene
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

Cortexolone
152-58-9

Cortexolone

Conditions
ConditionsYield
With water; potassium carbonate In methanol at 20℃; for 3h; Inert atmosphere;85%
With methanol; potassium hydrogencarbonate
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

A

Cortexolone
152-58-9

Cortexolone

B

9α-hydroxycortexolone
566-12-1

9α-hydroxycortexolone

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium dihydrogenphosphate; D-glucose; menadione; corn-steep liquor In water; N,N-dimethyl-formamide at 28℃; for 40h; Rhodococcus sp.;A 30%
B 50%
formaldehyd
50-00-0

formaldehyd

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

17α-hydroxy-17β-(1(3)H-imidazol-4-yl)-androst-4-en-3-one

17α-hydroxy-17β-(1(3)H-imidazol-4-yl)-androst-4-en-3-one

Conditions
ConditionsYield
With ammonium hydroxide; copper diacetate In ethanol for 6h; Heating;34%
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

2,2-dimethylpropanoic anhydride
1538-75-6

2,2-dimethylpropanoic anhydride

21-Acetoxy-17-trimethylacetoxy-4-pregnen-3,20-dion
86098-88-6

21-Acetoxy-17-trimethylacetoxy-4-pregnen-3,20-dion

Conditions
ConditionsYield
With dmap In diethylene glycol dimethyl ether at 80℃; for 96h;15%
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

17α-21-dihydroxy-5-α-pregnane-3,20-dione
312-99-2

17α-21-dihydroxy-5-α-pregnane-3,20-dione

Conditions
ConditionsYield
In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436, potato dextrose broth;8%
Multi-step reaction with 4 steps
1: H2SO4 / ethanol; dioxane / 1 h / Ambient temperature
2: H2 / 5percent Pd-C / ethanol; ethyl acetate / 14 h
3: 2N HCl / H2O
4: NaOH / methanol; dioxane
View Scheme
2-ethyl-2-methyl-1,3-dioxolane
126-39-6

2-ethyl-2-methyl-1,3-dioxolane

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

21-acetoxy-17α-hydroxy-3,3-ethylenedioxypregn-5-ene-20-one
913-44-0

21-acetoxy-17α-hydroxy-3,3-ethylenedioxypregn-5-ene-20-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid Entfernen des entstehenden Butanons;
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

semicarbazide hydrochloride
563-41-7

semicarbazide hydrochloride

21-acetoxy-17-hydroxy-pregn-4-ene-3,20-dione-3-semicarbazone
118978-39-5

21-acetoxy-17-hydroxy-pregn-4-ene-3,20-dione-3-semicarbazone

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

semicarbazide hydrochloride
563-41-7

semicarbazide hydrochloride

21-acetoxy-17-hydroxy-pregn-4-ene-3,20-dione disemicarbazone
119186-39-9

21-acetoxy-17-hydroxy-pregn-4-ene-3,20-dione disemicarbazone

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

17α,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetate
1249-67-8

17α,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetate

Conditions
ConditionsYield
With selenium(IV) oxide
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

14,17,21-trihydroxy-pregn-4-ene-3,20-dione
595-18-6

14,17,21-trihydroxy-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
mit Hilfe von Mycobacterium smegmatis;
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

17β-acetoxymethyl-17α-hydroxy-D-homo-androst-4-ene-3,17a-dione
100774-07-0

17β-acetoxymethyl-17α-hydroxy-D-homo-androst-4-ene-3,17a-dione

Conditions
ConditionsYield
With cyclohexanone; aluminum isopropoxide; toluene
With boron trifluoride diethyl etherate; acetic anhydride; acetic acid
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

21-acetoxy-17-hydroxy-pregna-4,6-diene-3,20-dione
6723-95-1

21-acetoxy-17-hydroxy-pregna-4,6-diene-3,20-dione

Conditions
ConditionsYield
With chloranil
Multi-step reaction with 2 steps
1: N-bromo-succinimide
2: 2,4,6-trimethyl-pyridine
View Scheme
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

21-acetoxy-6ξ-bromo-17-hydroxy-pregn-4-ene-3,20-dione
117064-36-5

21-acetoxy-6ξ-bromo-17-hydroxy-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
With N-Bromosuccinimide
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

21-acetoxy-17-hydroxy-pregn-4-ene-3,20-dione dioxime
119572-37-1

21-acetoxy-17-hydroxy-pregn-4-ene-3,20-dione dioxime

Conditions
ConditionsYield
With hydrogenchloride; hydroxylamine
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

4ξ,21-diacetoxy-5,17-dihydroxy-5ξ-pregnane-3,20-dione

4ξ,21-diacetoxy-5,17-dihydroxy-5ξ-pregnane-3,20-dione

Conditions
ConditionsYield
With osmium(VIII) oxide; dihydrogen peroxide; tert-butyl alcohol Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin;
cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

17α-hydroxy-17β-(1(3)H-imidazol-4-yl)-androst-4-en-3-one

17α-hydroxy-17β-(1(3)H-imidazol-4-yl)-androst-4-en-3-one

Conditions
ConditionsYield
With formaldehyd; ammonia; copper diacetate

640-87-9Relevant articles and documents

Effect of C-21 Substituents on the Elimination of a 17α-Acyloxy Group from 17α-(Acyloxy)-20-oxo Steroids

Solo, A. J.,Suto, Mark

, p. 2012 - 2013 (1980)

-

Julian et al.

, (1950)

A by the 3,17-dione steroid preparing steroid the synthetic method of the compound of

-

, (2017/03/14)

The invention discloses a synthetic method of steroid type drugs and intermediates, in particular relates to a synthetic method for preparing 17-hydroxy-20-ketone steroid compounds from 3,17-diketone steroids, and belongs to the field of synthesis of drugs. The method takes 3,17-diketone steroids as raw materials and adopts a conventional, environment-friendly, low-toxicity reagent, and the steroid type drugs such as cortisone, hydrocortisone, metacortandracin, or hydroprednisone, or intermediates 17alpha-hydroxy-20-ketone compounds are prepared simply and conveniently at high yield by selective protection of C3 or (and) C11-ketone group, Wittig reaction of C17, selective oxidization of 17(20)-position double bonds and halogenating replacement. The aftertreatment is simple, few three wastes are generated, the reaction selectivity is good, the yield is high, and byproducts anti-pregnancy steroidal drugs and steroidal compounds can be obtained. The raw materials are easy to get, the cost is low and the synthetic process is simple; the synthetic method is suitable for industrial production.

An efficient hemisynthesis of 20- and 21-[13C]-labeled cortexolone: A model for the study of skin sensitization to corticosteroids

Claudel, Emilie,Arbez-Gindre, Cecile,Berl, Valerie,Lepoittevin, Jean-Pierre

scheme or table, p. 3391 - 3398 (2010/02/28)

A method is described for the synthesis of isotopomers of cortexolone from the commercially available andros-4-ene-3, 17dione. The strategy is based on the use of K13CN for labeling at position 20 and of 13CH 3Mgl, generated in situ, for labeling at position 21. Because of the early introduction of the [13C] labeling, our efforts aimed at reproducible experimental procedures giving high yields with respect to the isotope containing precursors. During the development of this hemisynthesis, we noted that judicious choice of protective groups was essential as this could lead not only to mixtures or unstable intermediates but also influence considerably the output of reactions.

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