18,21-Dihydroxypregn-4-ene-3,20-dione

Base Information

• Chemical Name: 18,21-Dihydroxypregn-4-ene-3,20-dione
• CAS No.: 379-68-0
• Molecular Formula: C21H30O4
• Molecular Weight: 346.467
• European Community (EC) Number: 206-834-3
• DSSTox Substance ID: DTXSID90958920
• Nikkaji Number: J117.990J
• Wikipedia: 18-Hydroxy-11-deoxycorticosterone
• Wikidata: Q82939478
• Mol file: 379-68-0.mol

Synonyms:18,21-dihydroxy-4-pregnene-3,20-dione;18-hydroxydeoxycorticosterone

Chemical Property of 18,21-Dihydroxypregn-4-ene-3,20-dione

Chemical Property:

• Vapor Pressure: 1.06E-13mmHg at 25°C
• Melting Point: 171-173 °C
• Refractive Index: 1.577
• Boiling Point: 535.4 °C at 760 mmHg
• Flash Point: 291.7 °C
• PSA: 74.60000
• Density: 1.22 g/cm³
• LogP: 2.66830
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly, Sonicated), Methanol (Slightly, Heated)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 346.21440943
• Heavy Atom Count: 25
• Complexity: 623

Purity/Quality:

99%, ^*data from raw suppliers

11-Deoxy-18-hydroxycorticosterone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4C(=O)CO)CO
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4C(=O)CO)CO
• Description: 18-hydroxy-11-deoxy Corticosterone (18-OH-DOC) is a mineralocorticoid secreted by the zona fasciculata of the adrenal gland. Its biosynthesis is regulated by adrenocorticotropic hormone (ACTH; ) as well as angiotensin II , which increases 18-OH-DOC production in isolated human adrenal glomerulosa cells. 18-OH-DOC can be formed via conversion of 11-deoxy corticosterone (DOC; ) in human SK-MEL188 melanoma cells. 18-OH-DOC is an intermediate in the metabolism of progesterone and can be converted to aldosterone by the capsular portion of rat adrenal glands. Continuous infusion of 18-OH-DOC (200 μg/rat per day) increases systolic blood pressure in uninephrectomized saline-drinking rats. Plasma levels of 18-OH-DOC are elevated in a db/db mouse model of type 2 diabetes.
• Uses: 11-Deoxy-18-hydroxycorticosterone is an analog of Corticosterone (C695700); a glucocorticoid and intermediate in the biosynthesis of Aldosterone (A514700) which is an adrenocortical steroid isolated from the adrenal cortex.

Technology Process of 18,21-Dihydroxypregn-4-ene-3,20-dione

There total 5 articles about 18,21-Dihydroxypregn-4-ene-3,20-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

21-Hydroxyprogesterone (64-85-7) → aldosterone (6251-69-0) + Corticosterone (50-22-6) + 18-Hydroxydeoxycorticosterone (379-68-0)

Guidance literature:

With Krebs-Ringer-bicarbonate-glucose buffer; male CHBB-Thom rat adrenal mitochondria; NADPH; Kinetics; partial inhib. by cortisol;

DOI:10.1016/0039-128X(94)00064-J

Reference yield:

18,20-epoxy-pregna-4,20-dien-3-one (56896-04-9) → 18-Hydroxydeoxycorticosterone (379-68-0)

Guidance literature:

With 1,4-dioxane; osmium(VIII) oxide; anschliessendes Behandeln mit wss.Na₂SO₃;

DOI:10.1021/ja01513a068

Reference yield:

21-(dimethyl-oxy-amino)-18,20βF-epoxy-pregn-4-en-3-one (102543-82-8) → 18-Hydroxydeoxycorticosterone (379-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tert-butylbenzene

2: OsO₄; dioxane / anschliessendes Behandeln mit wss.Na₂SO₃

With 1,4-dioxane; osmium(VIII) oxide; tert-butylbenzene;

DOI:10.1021/ja01513a068

upstream raw materials:

21-Hydroxyprogesterone

18,20-epoxy-pregna-4,20-dien-3-one

21-(dimethyl-oxy-amino)-18,20β_F-epoxy-pregn-4-en-3-one

Refernces