56-47-3 Usage
Description
Deoxycorticosterone acetate (DOCA) is an endogenous neurosteroid derived from progesterone, which is found in the brain and peripheral circulation. It serves as both a mineralocorticoid and a glucocorticoid, playing a crucial role in the regulation of various physiological processes. DOCA is used to treat adrenocortical insufficiency or Addison's disease and has been shown to improve insulin sensitivity. It also acts as a precursor to glucocorticoid corticosterone and the GABAergic neuroactive steroid (3α,5α)-3,21-dihydroxypregnan-20-one. DOCA is an off-white solid and is available under the brand names Doca (Organon) and Percorten (Novartis). It was previously known as Deoxycortone.
Uses
1. Used in Adrenocortical/Mineralocorticoid Steroid Applications:
Deoxycorticosterone acetate is used as a mineralocorticoid and glucocorticoid for the treatment of adrenocortical insufficiency or Addison's disease. It helps regulate the body's electrolyte balance and immune response.
2. Used in Hypertensive Pregnancy Research:
Deoxycorticosterone acetate has been utilized to induce hypertensive pregnancy in research settings. This allows scientists to study the effects of various treatments and interventions on pregnant women with high blood pressure.
3. Used in Cardiovascular Function Studies:
DOCA has been employed to investigate the impact of low epicatechin dosing on the cardiovascular function of DOCA-salt hypertensive rats. This research helps to understand the potential benefits of epicatechin in managing hypertension and related cardiovascular issues.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 56-47-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 6 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 56-47:
(4*5)+(3*6)+(2*4)+(1*7)=53
53 % 10 = 3
So 56-47-3 is a valid CAS Registry Number.
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
56-47-3Relevant articles and documents
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Rakhit,Gut
, p. 1196 (1968)
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Regioselective esterification of polyhydroxylated steroids by Candida antarctica lipase B
Bertinotti, Anna,Carrea, Giacomo,Ottolina, Gianluca,Riva, Sergio
, p. 13165 - 13172 (2007/10/02)
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
Solyom, Sandor,Szilagyi, Katalin,Toldy, Lajos
, p. 153 - 160 (2007/10/02)
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.