Deltacortinene Acetate

Base Information

• Chemical Name: Deltacortinene Acetate
• CAS No.: 4380-55-6
• Molecular Formula: C23H28O5
• Molecular Weight: 384.472
• UNII: TTA4SP1HRQ
• Nikkaji Number: J512.096I
• Mol file: 4380-55-6.mol

Synonyms:Deltacortinene Acetate;4380-55-6;TTA4SP1HRQ;UNII-TTA4SP1HRQ;Prednisolone acetate impurity E [EP];17-Hydroxy-3,20-dioxopregna-1,4,9(11)-trien-21-yl acetate;21-(Acetyloxy)-17-hydroxypregna-1,4,9(11)-triene-3,20-dione;21-Acetoxy-17alpha-hydroxypregna-1,4,9(11)-triene-3,20-dione;SCHEMBL10414458;SBUSWJGDMXBNFJ-GACAOOTBSA-N;AKOS032430349;PREDNISOLONE ACETATE IMPURITY E [EP IMPURITY];1,4,9(11)-Pregnatriene-3,20-dione, 21-acetoxy-17-hydroxy-;17-hydroxy-3,20-dioxopregna-1,4,9 (11)-trien-21-yl acetate;17-Hydroxy-3,20-dioxopregna-1,4,9(11)-trien-21-yl acetate #;21-ACETOXY-17.ALPHA.-HYDROXYPREGNA-1,4,9(11)-TRIENE-3,20-DIONE;[2-[(8S,10S,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate

Chemical Property of Deltacortinene Acetate

Chemical Property:

• Melting Point: 222-223 °C
• Boiling Point: 556.9±50.0 °C(Predicted)
• PKA: 12.46±0.60(Predicted)
• PSA: 80.67000
• Density: 1.25±0.1 g/cm3(Predicted)
• LogP: 3.07770
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 384.19367399
• Heavy Atom Count: 28
• Complexity: 849

Purity/Quality:

99% ^*data from raw suppliers

DeltacortineneAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1(CCC2C1(CC=C3C2CCC4=CC(=O)C=CC43C)C)O
• Isomeric SMILES: CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(CC=C3[C@H]2CCC4=CC(=O)C=C[C@@]43C)C)O
• Uses: Deltacortinene Acetate is a glucocorticoid, an analog of Prednisolone (P703740), a synthetic corticosteroid; metabolically interconvertible with Prednisone (P703780).

Technology Process of Deltacortinene Acetate

There total 3 articles about Deltacortinene 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: 50.0%

prednisolone 21-acetate (52-21-1) → 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (37413-91-5) + pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (4380-55-6) + 2-((10S)-10,17-dimethyl-3-oxo-6,7,8,10,12,15,16,17-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate + C46H54O11S

Guidance literature:

With pyridine; thionyl chloride; In N,N-dimethyl-formamide; at 20 ℃; Reagent/catalyst; Temperature;

DOI:10.1016/j.steroids.2018.06.007

Reference yield:

anecortave (7753-60-8) → Anecortave (10184-70-0) + pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (4380-55-6) + (10S,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one (10184-69-7) + pregna-1,4,9(11)-triene-17α,20β,21-triol-3-one

Guidance literature:

With Nocardioides simplex VKM Ac-2033D; In phosphate buffer; at 28 ℃; pH=7.5; Further Variations:; pH-values; Product distribution; Enzymatic reaction;

DOI:10.1016/S0039-128X(03)00043-6

Reference yield:

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione (898-84-0) → pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (4380-55-6)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic anhydride; sulfuric acid / dichloromethane / 2 h / -10 °C / Green chemistry

2: potassium carbonate / methanol / 25 °C / Green chemistry

3: 1H-imidazole / tetrahydrofuran / 2 h / 0 - 5 °C / Inert atmosphere; Green chemistry

4: chloro-trimethyl-silane / tetrahydrofuran / 10 h / -70 °C / Inert atmosphere; Green chemistry

With 1H-imidazole; chloro-trimethyl-silane; sulfuric acid; acetic anhydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

anecortave

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione

prednisolone 21-acetate

Downstream raw materials:

2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

21-Deacetyldeflazacort

deflazacort

prednisolone 21-acetate