(10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione

Base Information

• Chemical Name: (10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione
• CAS No.: 53-03-2
• Molecular Formula: C21H26O5
• Molecular Weight: 358.434
• Hs Code.: 2937210000
• NSC Number: 757289
• Mol file: 53-03-2.mol

Synonyms:(10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione;Spectrum_000828;Spectrum2_001292;Spectrum3_000756;Spectrum4_000971;Spectrum5_000988;BSPBio_002372;KBioGR_001341;KBioSS_001308;DivK1c_000666;SPECTRUM1500499;SPBio_001323;SCHEMBL13043964;HMS502B08;KBio1_000666;KBio2_001308;KBio2_003876;KBio2_006444;KBio3_001592;NINDS_000666;HMS1920J16;HMS2092A17;HMS3373K22;Pharmakon1600-01500499;CCG-39230;NSC757289;NSC-757289;IDI1_000666;SMP2_000307;NCGC00178682-01;SBI-0051490.P003;AB00052078_02;A829356;AA-504/07226001;SR-05000002076;SR-05000002076-1;BRD-A62525898-001-02-9;BRD-A62525898-001-04-5;(10R,13S,17R)-10,13-dimethyl-17-oxidanyl-17-(2-oxidanylethanoyl)-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione;(10R,13S,17R)-17-hydroxy-17-(2-hydroxy-1-oxoethyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione;17-glycoloyl-17-hydroxy-10,13-dimethyl-7,8,9,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene-3,11(6H)-dione

Chemical Property of (10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.51E-15mmHg at 25°C
• Melting Point: 236-238 °C(lit.)
• Refractive Index: 170 ° (C=0.5, Dioxane)
• Boiling Point: 573.7 °C at 760 mmHg
• PKA: 12.36±0.60(Predicted)
• Flash Point: 314.8 °C
• PSA: 91.67000
• Density: 1.3 g/cm³
• LogP: 1.76580
• Storage Temp.: Refrigerator
• Solubility.: Practically insoluble in water, slightly soluble in ethanol (96 per cent) and in methylene chloride. It shows polymorphism (5.9).
• Water Solubility.: 115mg/L(25 oC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 358.17802393
• Heavy Atom Count: 26
• Complexity: 764

Purity/Quality:

99% ^*data from raw suppliers

Prednisone-d4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,C,F
• Hazard Codes: Xn,C,F
• Statements: 63-34-11
• Safety Statements: 36/37/39-45-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CC(=O)C3C(C1CCC2(C(=O)CO)O)CCC4=CC(=O)C=CC34C
• Isomeric SMILES: C[C@]12CC(=O)C3C(C1CC[C@@]2(C(=O)CO)O)CCC4=CC(=O)C=C[C@]34C
• Uses: Adrenocortical steroid. Glucocorticoid, antiinflammatory. Downregulates TNF-α production and NF-κB expression Prednisone is used for the same indications as cortisone for inflammatory processes, allergies, and adrenal gland insufficiency; however, it is somewhat more active than cortisone and has less of an effect on mineral volume.
• Indications: Prednisone 2.5 to 7.5 mg, administered at night or dexamethasone 0.25 to 0.75 mg are useful in female patients, with severe acne unresponsive to conventional therapy, who suffer from adrenal gland overproduction of androgens such as congenital adrenal hyperplasia.

Technology Process of (10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione

There total 15 articles about (10R,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-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: 94.0%

Cortisone (53-06-5) → Prednison (53-03-2)

Guidance literature:

With Rhodococcus coprophilus DSM 43347; In dimethyl sulfoxide; at 30 ℃; for 24h; Reagent/catalyst; regiospecific reaction; Green chemistry;

DOI:10.3390/molecules25092192

Reference yield: 89.0%

prednisone acetate (125-10-0) → Prednison (53-03-2)

Guidance literature:

With di(n-butyl)tin oxide; In methanol; for 4h; Heating;

DOI:10.1016/j.steroids.2006.10.004

Reference yield: 30.0%

Cortisone (53-06-5) → Prednison (53-03-2) + 17α,20β,21-trihydroxy-1,4-pregnadiene-3,11-dione (600-92-0)

Guidance literature:

With Rhodococcus rhodnii DSM 43960; In dimethyl sulfoxide; for 24h; Green chemistry; Enzymatic reaction;

DOI:10.3390/molecules26051352

upstream raw materials:

Cortisone

prednisone acetate

prednisolon

Prednisone pivalate

Downstream raw materials:

prednisone

Cortisone

androsta-1,4-diene-3,11,17-trione

11β,17α,20β,21-tetrahydroxy-1,4-pregnadiene-3-one

Refernces

• 1、 Caspi,E. et al.. "". . p. 767 - 775. Retrieved 1962.
• 2、 Cacciari, R. Daniel,Reynoso, Eugenia,Montejano, Hernán A.,Biasutti, M. Alicia. "Photodegradation of prednisolone under UVB solar irradiation. Role of photogenerated ROS in the degradation mechanism". . p. 1717 - 1726. Retrieved 2017.
• 3、 -. "Preparation method of prednisone". Paragraph 0012; 0029; 0032-0033; 0036-0037; 0040. . Retrieved 2021/03/05.