20(S)-Hydroxy Prednisolone

Base Information

• Chemical Name: 20(S)-Hydroxy Prednisolone
• CAS No.: 2299-46-9
• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.466
• UNII: NN79HDK6LV
• DSSTox Substance ID: DTXSID90553373
• Metabolomics Workbench ID: 73600
• Nikkaji Number: J371.860C
• Wikidata: Q82433937
• Mol file: 2299-46-9.mol

Synonyms:2299-46-9;20(S)-Hydroxy Prednisolone;20a-Hydroxy Prednisolone;NN79HDK6LV;UNII-NN79HDK6LV;20beta-hydroxyprednisolone;20beta-Dihydroprednisolone;20alpha-dihydroprednisolone;Pregna-1,4-dien-3-one, 11,17,20,21-tetrahydroxy-, (11beta,20S)-;Prednisolone impurity G [EP];(11beta,20S)-11,17,20,21-Tetrahydroxypregna-1,4-dien-3-one;(8S,9S,10R,11S,13S,14S,17R)-17-[(1S)-1,2-dihydroxyethyl]-11,17-dihydroxy-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one;11beta,17,20beta,21-Tetrahydroxypregna-1,4-dien-3-one;(20S)-Hydroxyprednisolone;20|A-Hydroxy Prednisolone;20S-hydroxyprednisolone;20alpha-Hydroxyprednisolone;SCHEMBL8859759;DTXSID90553373;CHEBI:166776;20beta-Dihydro-prednisolone (M-II);PREDNISOLONE IMPURITY G [EP IMPURITY];J-014931;11beta,17alpha,20S,21-Tetrahydroxy-pregna-1,4-dien-3-one;Pregna-1,4-dien-3-one, 11,17,20,21-tetrahydroxy-, (11beta,20S);(8S, 9S, 10R, 11S, 13S, 14S, 17R)-17-[(1S)-1, 2-dihydroxyethyl]-11, 17-dihydroxy-10, 13-dimethyl-7, 8, 9, 11, 12, 14, 15, 16-octahydro-6H-cyclopenta[a]phenanthren-3-one

Chemical Property of 20(S)-Hydroxy Prednisolone

Chemical Property:

• PSA: 97.99000
• LogP: 1.34940
• XLogP3: 1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 362.20932405
• Heavy Atom Count: 26
• Complexity: 684

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

20(S)-HydroxyPrednisolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC(C3C(C1CCC2(C(CO)O)O)CCC4=CC(=O)C=CC34C)O
• Isomeric SMILES: C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@]2([C@H](CO)O)O)CCC4=CC(=O)C=C[C@]34C)O
• Uses: 20(S)-Hydroxy Prednisolone (Prednisolone EP Impurity G) is a Prednisolone (P703740) metabolite.

Technology Process of 20(S)-Hydroxy Prednisolone

There total 7 articles about 20(S)-Hydroxy Prednisolone 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:

→ 11β,17α,20β,21-Tetrahydroxypregna-1.4-dien-3-on (2299-46-9,2782-72-1,4450-85-5,15847-24-2)

Guidance literature:

Pregnisolen durch mikrobiol. Reduktion (Methode A);

DOI:10.1007/BF00571211

Reference yield:

→ 1,4-Pregnadien-11β,17α,20β,21-tetrol-3-on (2299-46-9,2782-72-1,4450-85-5,15847-24-2)

Guidance literature:

Hydrocortison, Streptomyces-Arten (St. flareolus); (vermutliche Entstehg. der Verb.); (Nebenprod.);

Reference yield:

methyl 11β,17α,20α-trihydroxy-3-oxo-1,4-pregnadiene-21-oate (97232-42-3) → (20S)-11β,17,20,21-tetrahydroxy-3-oxo-1,4-pregnadiene (2299-46-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 0.75h; Heating;

DOI:10.1021/jm00395a011

upstream raw materials:

prednisolon

methyl 11β,17α,20α-trihydroxy-3-oxo-1,4-pregnadiene-21-oate

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

11β,17α,20α,21-Tetrahydroxy-3-oxo-pregnadien-(1,4)-17α,21-cyclopentanonid

Refernces