Cortisone acetate

Base Information

• Chemical Name: Cortisone acetate
• CAS No.: 50-04-4
• Molecular Formula: C23H30O6
• Molecular Weight: 402.488
• Hs Code.: 32041200
• NSC Number: 756703
• Mol file: 50-04-4.mol

Synonyms:Cortisone-21-acetate;21-Acetoxypregnen-17a-ol-3,11,20-trione;

Chemical Property of Cortisone acetate

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 237-240 °C(lit.)
• Refractive Index: 212 ° (C=1, MeOH)
• Boiling Point: 567.8 °C at 760 mmHg
• PKA: 12.32±0.60(Predicted)
• Flash Point: 311.2 °C
• PSA: 97.74000
• Density: 1.28 g/cm³
• LogP: 2.56060
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, freely soluble in methylene chloride, soluble in dioxan, sparingly soluble in acetone, slightly soluble in ethanol (96 per cent) and in methanol.
• Water Solubility.: 19mg/L(25 oC)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 402.20423867
• Heavy Atom Count: 29
• Complexity: 827

Purity/Quality:

99% ^*data from raw suppliers

Cortisone Acetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1(CCC2C1(CC(=O)C3C2CCC4=CC(=O)CCC34C)C)O
• Isomeric SMILES: CC(=O)OCC(=O)[C@]1(CCC2[C@@]1(CC(=O)C3C2CCC4=CC(=O)CC[C@]34C)C)O
• Description: Cortisone acetate is a synthetic glucocorticoid with anti-inflammatory properties. It decreases the size of Bacillus Calmette-Guérin (BCG) vaccine-induced dermal lesions and tuberculin reactions in rabbits when administered at 2 mg/kg on alternate days over the course of 46 days. It also reduces the number and percentage of activated lesion-infiltrating mononuclear cells and decreases the amount of caseous necrosis and ulceration. Cortisone acetate (2.5 mg/kg per day, s.c.) slows tissue regeneration in a rabbit model of wound healing. It also decreases the number of dexamethasone binding sites on isolated human lymphocytes by 30%. Formulations containing cortisone acetate have been used to relieve inflammation, pruritic manifestations of corticosteroid-responsive dermatoses, and in the treatment of immune and allergic disorders.
• Uses: Cortisone Acetate (Hydrocortisone Acetate EP Impurity D) is a glucocorticoid. Cortisone Acetate is an antiinflammatory agent. Cortisone Acetate is bioavailable and readily converted to the therapeutically active form, Hydrocotisone (H714615). Cortisone Acetate is a glucocorticoid. Cortisone Acetate is an antiinflammatory agent. Cortisone Acetate is bioavailable and readily converted to the therapeutically active form, Hydrocotisone (H71461 5).
• Therapeutic Function: Glucocorticoid

Technology Process of Cortisone acetate

There total 32 articles about Cortisone acetate 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: 95.8%

anecortave (7753-60-8) → Cortisone acetate (50-04-4)

Guidance literature:

anecortave; With tetrafluoroboric acid; In dichloromethane; acetone; at -5 - 0 ℃; for 5h; Inert atmosphere;

With Jones reagent; In dichloromethane; acetone; at 0 - 5 ℃; for 4h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

Reference yield: 93.0%

Acetic acid 2-hydroxy-2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl ester → Cortisone acetate (50-04-4)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 50 ℃; for 3h;

DOI:10.1016/0040-4039(94)80038-3

Reference yield: 93.0%

hydrocortisone acetate → Cortisone acetate (50-04-4)

Guidance literature:

With [2,2]bipyridinyl; trimethylsilyl trifluoromethanesulfonate; bis(acetoxy)iodylbenzene; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/acs.joc.1c00375

upstream raw materials:

hydrocortisone acetate

21-acetoxy-17-hydroxy-5β-pregnane-3,11,20-trione

21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione

acetic acid

Downstream raw materials:

Cortisone

prednisone acetate

4-Chlor-cortison-21-acetat

21-acetoxy-17-hydroxy-5α-pregnane-3,11,20-trione

Refernces

• 1、 -. "Method for treating prednisone acetate mother liquor". Paragraph 0034-0066. . Retrieved 2021/06/02.
• 2、 -. "9-site dehalogenation preparation method of 9-halogenated steroid hormone compound". Paragraph 0023-0025. . Retrieved 2020/07/15.