56-47-3

Basic information

• Product Name: Deoxycorticosterone acetate
• Synonyms: 11-deoxycorticosterone21-acetate;20-dione,21-hydroxy-pregn-4-ene-acetate;21-acetoxy-3,20-diketopregn-4-ene;21-Acetyloxypregn-4-ene-3,20-dione;21-hydroxypregn-4-ene-3,20-dione21-acetate;4-pregnene-3,20-dione-21-olacetate;arcort;bio-corten
• CAS NO: 56-47-3
• Molecular Formula: C₂₃H₃₂O₄
• Molecular Weight: 372.5
• EINECS: 200-275-9
• Product Categories: Biochemistry;Hydroxyketosteroids;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;PERCOTEN;Hormone Drugs;Inhibitors
• Mol File: 56-47-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 157°C
• Boiling Point: 421.94°C (rough estimate)
• Flash Point: 218 °C
• Appearance: Off-white solid
• Density: 1.0415 (rough estimate)
• Vapor Pressure: 2.74E-10mmHg at 25°C
• Refractive Index: 175 ° (C=1, Dioxane)
• Storage Temp.: Refrigerator
• Solubility: H2O: insoluble
• Water Solubility: 4mg/L(25 oC)
• Merck: 2901
• BRN: 2570798
• CAS DataBase Reference: Deoxycorticosterone acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Deoxycorticosterone acetate(56-47-3)
• EPA Substance Registry System: Deoxycorticosterone acetate(56-47-3)

Safety Data

• Safety Statements: 22-24/25
• RIDADR: UN 2811
• WGK Germany: 3
• RTECS: HG0525000
• HazardClass: IRRITANT
• Hazardous Substances Data: 56-47-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 56-47-3 differently. You can refer to the following data:
1. Adrenocortical/mineralocorticoid Steroid.
2. Deoxycorticosterone acetate has been used to induce hypertensive pregnancy. It has also been used to investigate the effect of low epicatechin dosing on the cardiovascular function of deoxycorticosterone acetate (DOCA)-salt hypertensive rats.

Brand name

Doca (Organon); Percorten (Novartis) [Name previously used: Deoxycortone.].

General Description

Deoxycorticosterone acetate is an endogenous neurosteroid found in brain and peripheral circulation, which is produced by progesterone. It is both a mineralocorticoid and a glucocorticoid. It is used to treat adrenocortical insufficiency or Addison′s disease. Deoxycorticosterone acetate improves insulin sensitivity. It acts as a precursor to glucocorticoid corticosterone and the GABAergic neuroactive steroid (3α,5α)-3,21-dihydroxypregnan-20-one.

Purification Methods

11-Deoxycorticosterone acetate recrystallises from EtOH as needles or Me2CO/hexane, and sublimes at high vacuum. It is partly soluble in MeOH, Me2CO, Et2O and dioxane but insoluble in H2O. [Reichstein & Euw Helv Chim Acta 23 136 1940, Romo et al. J Am Chem Soc 79 5034 1957; NMR: Shoolery & Rogers J Am Chem Soc 80 5121 1959, Beilstein 8 IV 2195.]

InChI:InChI=1/C23H32O4/c1-14(24)27-13-21(26)20-7-6-18-17-5-4-15-12-16(25)8-10-22(15,2)19(17)9-11-23(18,20)3/h12,17-20H,4-11,13H2,1-3H3/t17?,18?,19?,20-,22+,23+/m1/s1

Synthetic route

21-Hydroxyprogesterone (64-85-7) + acetic anhydride (108-24-7) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With pyridine In benzene	89%
With pyridine
With pyridine Ambient temperature;
With pyridine

3,20-dioxo-pregna-1,4-dien-21-yl acetate (1171-90-0) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With thallium(III) nitrate trihydrate In diethylene glycol dimethyl ether for 24h; Ambient temperature;	25%

pyridine (110-86-1) + 20ξ-hydroxy-3-oxo-pregnen-(4)-al-(21) (934167-52-9) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
beim anschliessenden Behandeln mit Acetanhydrid;

Ketene (463-51-4) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With acetone
With acetone

tetrachloromethane (56-23-5) + N-Bromosuccinimide (128-08-5) + 24,24-diphenyl-chola-4,20(22)ξ,23-trien-3-one (15086-91-6) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
Reaktion ueber mehrere Stufen;

21-acetoxypregnenolone (566-78-9) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With aluminum tri-tert-butoxide; acetone
With chloroform; bromine Behandeln des erhaltenen Dibromids mit CrO3 in Essigsaeure und Behandeln einer Loesung des Reaktionsprodukts mit wss. CrCl2-Loesung unter Kohlendioxyd;
With chloroform; bromine Erwaermen des Reaktionsprodukts mit Zink-Pulver und Natriumacetat in Aether und anschliessend mit Essigsaeure und Erhitzen des danach isolierten Reaktionsprodukts mit Essigsaeure;
With chloroform; bromine Erwaermen des Reaktionsprodukts mit Zink-Pulver und Natriumacetat in Aether und anschliessend mit Essigsaeure und Erhitzen des danach isolierten Reaktionsprodukts mit Essigsaeure;

21-chloropregn-4-ene-3,20-dione (26987-64-4) + sodium acetate (127-09-3) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With acetic acid

21-acetoxy-3β-formyloxy-pregn-5-en-20-one (115098-53-8) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With cyclohexanone; aluminum isopropoxide

11-deoxy-21-iodocorticosterone (20576-46-9) + potassium acetate (127-08-2) → deoxycorticosterone acetate (56-47-3)

24,24-diphenyl-chola-4,20(22)ξ,23-trien-3-one (15086-91-6) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With tetrachloromethane; N-Bromosuccinimide unter Belichtung anschliessend des Reaktionsprodukts mit Kaliumacetat in Essigsaeure und Behandeln einer Loesung des danach isolierten Reaktionsprodukts in Essigsaeure und 1.2-Dichlor-aethan mit CrO3 in wss. Essigsaeure;

Progesterone (57-83-0) + lead(IV) tetraacetate (546-67-8) + acetic acid (64-19-7) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
at 75 - 85℃;

21-chloro-5β-pregnane-3,20-dione (111438-07-4) + acetic acid (64-19-7) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With bromine Erhitzen der Reaktionsloesung mit Kaliumacetat;
With bromine Erhitzen der Reaktionsloesung mit Kaliumacetat;

21-Diazoprogesterone (53892-00-5) + acetic acid (64-19-7) → deoxycorticosterone acetate (56-47-3)

vinyl acetate (108-05-4) + 21-Hydroxyprogesterone (64-85-7) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With Candida antarctica lipase B In tetrahydrofuran at 45℃; Rate constant;

17-hydroxy-20ξ.21-diacetoxy-17βH-pregnen-(4)-one of mp: 162-163 → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With toluene; zinc

17-hydroxy-20ξ.21-diacetoxy-17βH-pregnen-(4)-one of mp: 180-181 → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With toluene; zinc

21-chloro-3β-hydroxy-pregnen-(5)-one-(20) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
With chloroform; bromine Behandeln des Reaktionsprodukts mit CrO3 in Essigsaeure und Erwaermen des danach erhaltenen Reaktionsprodukts mit Natriumacetat und Essigsaeure, zuletzt unter Zusatz von Zink-Pulver;
With chloroform; bromine Behandeln des Reaktionsprodukts mit CrO3 in Essigsaeure und Erwaermen des danach erhaltenen Reaktionsprodukts mit Natriumacetat und Essigsaeure, zuletzt unter Zusatz von Zink-Pulver;

21-acetoxy-5β-pregnane-3,20-dione (2402-25-7) + bromine (7726-95-6) + acetic acid (64-19-7) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
und Erhitzen des Reaktionsprodukts mit Pyridin;
und Erhitzen des Reaktionsprodukts mit Kaliumacetat;
und Erhitzen des Reaktionsprodukts mit Kaliumacetat;

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + 3β.5.14.21-tetrahydroxy-3β.14β-pregnanone-(20) (33439-96-2) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
Behand. des Reakt.pr. mit Acetanhydrid und Pyridin, Hydr.in Essigsaeure an Platin, Behand. mit CrO3 in Essigsaeure und Erhitzen mit Essigsaeure;

21-acetoxypregnenolone (566-78-9) + bromine (7726-95-6) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
Behandlung des erhaltenen Dibromids mit CrO3 in Essigsaeure und anschliessende Debromierung;
Behandlung des erhaltenen Dibromids mit CrO3 in Essigsaeure und anschliessende Debromierung;

3,20-dioxo-4-pregnen-21-al (853-27-0) + acetic acid (64-19-7) + zinc-powder → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin;

21-Hydroxyprogesterone (64-85-7) + acetic anhydride (108-24-7) → deoxycorticosterone acetate (56-47-3) + 3,21-diacetoxy-pregna-3,5-dien-20-one (115097-15-9)

Conditions	Yield
With toluene-4-sulfonic acid for 0.0833333h; microwave irradiation;

21-Benzoyloxy-4-pregnen-3,20-dion (104203-45-4) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / KHCO3 (saturated aq. sol.) / 3 h / Heating 2: 89 percent / pyridine / benzene View Scheme

21-Benzoyloxy-4-pregnen-3,20-dion-3-ethylendithioacetal (104203-44-3) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent / HgO, BF3-Et2O / tetrahydrofuran; H2O / Ambient temperature 2: 67 percent / KHCO3 (saturated aq. sol.) / 3 h / Heating 3: 89 percent / pyridine / benzene View Scheme

3β-acetoxyetienic acid (7150-18-7) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: benzene; thionyl chloride 2: diethyl ether / Behandeln des erhaltenen 3β-Acetoxy-21-diazo-pregnen-(5)-ons-(20) mit methanol. KOH 3: acetic acid 4: bromine; chloroform / Erwaermen des Reaktionsprodukts mit Zink-Pulver und Natriumacetat in Aether und anschliessend mit Essigsaeure und Erhitzen des danach isolierten Reaktionsprodukts mit Essigsaeure View Scheme

3β-acetoxy-5-etienic acid chloride (7429-97-2) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether / Behandeln des erhaltenen 3β-Acetoxy-21-diazo-pregnen-(5)-ons-(20) mit methanol. KOH 2: acetic acid 3: bromine; chloroform / Erwaermen des Reaktionsprodukts mit Zink-Pulver und Natriumacetat in Aether und anschliessend mit Essigsaeure und Erhitzen des danach isolierten Reaktionsprodukts mit Essigsaeure View Scheme

21-diazo-3β-hydroxy-pregn-5-en-20-one (33769-71-0) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid 2: bromine; chloroform / Erwaermen des Reaktionsprodukts mit Zink-Pulver und Natriumacetat in Aether und anschliessend mit Essigsaeure und Erhitzen des danach isolierten Reaktionsprodukts mit Essigsaeure View Scheme
Multi-step reaction with 2 steps 1: acetone; aluminium tert-butylate; benzene / 14-stdg. bzw. 20-taegiges Behandeln bei Siedetemperatur bzw. bei Raumtemperatur View Scheme

Progesterone (57-83-0) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: iodine View Scheme
Multi-step reaction with 7 steps 2: benzene; toluene-4-sulfonic acid 3: pyridine 4: benzene; sodium ethylate; diethyl ether 5: ethanolic KOH 6: iodine / anschliessend Behandeln mit wss. KOH View Scheme
Multi-step reaction with 8 steps 2: benzene; toluene-4-sulfonic acid 3: pyridine 4: benzene; sodium ethylate; diethyl ether 5: aqueous acetic acid 7: iodine / anschliessend Behandeln mit wss. KOH View Scheme

3β-hydroxypregn-5-ene-16,20-dione (911442-53-0) → deoxycorticosterone acetate (56-47-3)

Conditions	Yield
Multi-step reaction with 6 steps 2: toluene-4-sulfonic acid 5: palladium/charcoal; ethyl acetate / Hydrogenation 6: cyclohexanone; aluminium isopropylate View Scheme

deoxycorticosterone acetate (56-47-3) → 21-hydroxy-5β-pregnane-3,20-dione (303-01-5) + 4,5-epoxy-21-hydroxypregnane-3,20-dione (111464-71-2)

Conditions	Yield
With sodium hydroxide; 1-imidazolylsulfonylimidazolide; dihydrogen peroxide In tert-butyl alcohol for 3h;	A 29% B 62%
With sodium hydroxide; 1-imidazolylsulfonylimidazolide; dihydrogen peroxide In tert-butyl alcohol for 3h;	A 29% B 62%

deoxycorticosterone acetate (56-47-3) → (3β,5α)-3,21-dihydroxypregnan-20-one (567-02-2, 567-03-3, 800-10-2, 33995-21-0, 51548-31-3, 108450-73-3, 567-01-1) + 5α-pregnan-21-ol-3,20-dione (298-36-2)

Conditions	Yield
In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436, potato dextrose broth;	A 4% B 44%

formaldehyd (50-00-0) + deoxycorticosterone acetate (56-47-3) → 17β-(1(3)H-imidazol-4-yl)-androst-4-en-3-one (100323-02-2)

Conditions	Yield
With ammonium hydroxide; copper diacetate In ethanol for 6h; Heating;	17%

Isopropenyl acetate (108-22-5) + deoxycorticosterone acetate (56-47-3) → 3,21-diacetoxy-pregna-3,5-dien-20-one (115097-15-9)

Conditions	Yield
With toluene-4-sulfonic acid

hydrogen cyanide (74-90-8) + deoxycorticosterone acetate (56-47-3) → 22-acetoxy-20-hydroxy-3-oxo-23,24-dinor-20ξH-chol-4-ene-21-nitrile

deoxycorticosterone acetate (56-47-3) → 21-Hydroxyprogesterone (64-85-7)

Conditions	Yield
With methanol; potassium hydrogencarbonate
With methanol; potassium carbonate

deoxycorticosterone acetate (56-47-3) → 3,20-dioxo-pregna-1,4-dien-21-yl acetate (1171-90-0)

Conditions	Yield
With selenium(IV) oxide; acetic acid; tert-butyl alcohol
mit Hilfe von Corynebacterium simplex;
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene

deoxycorticosterone acetate (56-47-3) → 14,21-dihydroxy-pregn-4-ene-3,20-dione (595-71-1)

Conditions	Yield
mit Hilfe von Mucor griseo-cyanus;

deoxycorticosterone acetate (56-47-3) → 4-pregnen-11α,21-dionl-3,20-dione (600-67-9)

Conditions	Yield
mit Hilfe von Rhizopus nigricans;

deoxycorticosterone acetate (56-47-3) → 6β,21-dihydroxypregna-4-en-3,20-dione (298-65-7)

Conditions	Yield
mit Hilfe von Rhizopus arrhizus;

deoxycorticosterone acetate (56-47-3) → pregnanediol (80-92-2)

Conditions	Yield
biochemische Umwandlung;

deoxycorticosterone acetate (56-47-3) → pregn-4-ene-3β,20βF,21-triol (22630-66-6)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride; diethyl ether

deoxycorticosterone acetate (56-47-3) → 16α,21-dihydroxy-5β-pregnane-3,20-dione + 16α,21-Dihydroxyprogesterone (601-39-8)

Conditions	Yield
mit Hilfe von Streptomyces argenteolus;

deoxycorticosterone acetate (56-47-3) → 21-acetoxy-pregn-4-ene-3β,20βF-diol (112685-38-8)

Conditions	Yield
With sodium tetrahydroborate

deoxycorticosterone acetate (56-47-3) → 9α,21-dihydroxyprogesterone (640-39-1)

Conditions	Yield
mit Hilfe von Mucor parasiticus;

deoxycorticosterone acetate (56-47-3) → 21-acetoxy-6β-hydroxy-pregn-4-ene-3,20-dione (96346-36-0)

Conditions	Yield
With Isopropenyl acetate; toluene-4-sulfonic acid anschliessende Umsetzung mit Monoperoxyphthalsaeure;

deoxycorticosterone acetate (56-47-3) → 21-acetoxy-4β,5-dichloro-5α-pregnane-3,20-dione (114398-19-5)

Conditions	Yield
With chlorine; propionic acid

deoxycorticosterone acetate (56-47-3) → 21-acetoxy-3,3-dihydroperoxy-pregn-4-en-20-one (119076-63-0)

Conditions	Yield
With diethyl ether; dihydrogen peroxide

deoxycorticosterone acetate (56-47-3) → 4ξ,21-diacetoxy-5-hydroxy-5ξ-pregnane-3,20-dione (122703-58-6)

Conditions	Yield
With osmium(VIII) oxide; dihydrogen peroxide folgende Umsetzung mit Acetanhydrid in Pyridin;

Upstream product

• 463-51-4 Ketene 
• 566-78-9 21-acetoxypregnenolone 
• 115098-53-8 21-acetoxy-3β-formyloxy-pregn-5-en-20-one 
• 57-83-0 Progesterone 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 108-05-4 vinyl acetate 
• 64-85-7 21-Hydroxyprogesterone 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 33439-96-2 3β.5.14.21-tetrahydroxy-3β.14β-pregnanone-(20) 
• 7726-95-6 bromine 
• 853-27-0 3,20-dioxo-4-pregnen-21-al 
• 108-24-7 acetic anhydride 

Downstream Products

• 64-85-7 17-desoxycorticosterone 
• 2402-25-7 21-acetoxy-5β-pregnane-3,20-dione 
• 122723-78-8 Benzoic acid 17-(2-acetoxy-acetyl)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester 
• 21589-90-2 21-hydroxypregn-4,6-diene-3,20-dione 21-acetate 
• 601-39-8 16α,21-Dihydroxyprogesterone 
• 80-92-2 pregnanediol 
• 600-67-9 4-pregnen-11α,21-dionl-3,20-dione 
• 595-71-1 14α,21-Dihydroxy-pregnen-(4)-dion-(3,20) 
• 1171-90-0 3,20-dioxo-pregna-1,4-dien-21-yl acetate 
• 64-85-7 21-Hydroxyprogesterone 
• 567-02-2 (3β,5α)-3,21-dihydroxypregnan-20-one 
• 298-36-2 5α-pregnan-21-ol-3,20-dione 
• 302-97-6 androst-4-en-3-one-17β-carboxylic acid 

Relevant articles and documents

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Regioselective esterification of polyhydroxylated steroids by Candida antarctica lipase B

The regioselectivity of Candida antarctica lipase B towards the acetylation of polyhydroxylated steroids has been systematically investigated. The enzyme showed a marked preference for the alcoholic moieties on the A ring and: on the steroidal side chain, making it possible the selective acylation at the positions 3 or 21 of polyhydroxy steroids. Acylation with the synthetically useful esters chloroacetate and levulinate was also accomplished, whereas esterification with benzoate and pivaloate was unsuccessful.

New Synthesis of the Corticosterone Side-Chain

Condensation reactions between azlactone 2 and 17-ketosteroids 1 followed by opening of the azlactone ring with sodium methanolate yields methyl 20-benzoylamino-17(20)-pregnen-21-oates 6.Reduction of the ester and subsequent hydrolysis produce compounds with the corticosterone side-chain as well as a ring-closed product of new type.