2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyacetic acid

Base Information

• Chemical Name: 2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyacetic acid
• CAS No.: 62358-12-7
• Molecular Formula: C21H28O6
• Molecular Weight: 376.45
• DSSTox Substance ID: DTXSID20977907
• Mol file: 62358-12-7.mol

Synonyms:11,17,20-trihydroxy-3-oxo-1,4-pregnadien-21-oic acid;20-dihydroprednisolonic acid;20-dihydroprednisolonic acid, (11-beta,20S)-isomer;20-dihydroprednisolonic acid, (11beta,20R)-isomer

Chemical Property of 2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyacetic acid

Chemical Property:

• Vapor Pressure: 3.92E-18mmHg at 25°C
• Melting Point: >213°C (dec.)
• Boiling Point: 623°Cat760mmHg
• Flash Point: 344.6°C
• PSA: 115.06000
• Density: 1.38g/cm³
• LogP: 1.44170
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 376.18858861
• Heavy Atom Count: 27
• Complexity: 756

Purity/Quality:

99%min ^*data from raw suppliers

20ξ-DihydroprednisolonicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC(C3C(C1CCC2(C(C(=O)O)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(C(=O)O)O)O)CCC4=CC(=O)C=C[C@]34C)O
• Uses: 20ξ-Dihydroprednisolonic acid is a derivative of Prednisolone (P703740), a glucocorticosteroid that is used to treat patients with chronic obstructive pulmonary disease (COPD).

Technology Process of 2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyacetic acid

There total 6 articles about 2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyacetic acid 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: 72.0%

prednisolon (50-24-8,8056-11-9) → (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) + 11β,17α,20α-trihydroxy-3-oxo-1,4-pregnadien-21-oic acid (62358-12-7)

Guidance literature:

With potassium hydroxide; 2,6-dichloro-4-[(4-hydroxyphenyl)imino]-2,5-cyclohexadien-1-one sodium; In ethanol; for 10h; Ambient temperature;

DOI:10.1055/s-1981-29603

Reference yield: 70.0%

→ 20-dihydroprednisolonic acid + 11β,17α,20α-trihydroxy-3-oxo-1,4-pregnadien-21-oic acid (62358-12-7)

Guidance literature:

Reference yield: 56.0%

prednisolon (50-24-8,8056-11-9) → 11β,17α,20α-trihydroxy-3-oxo-1,4-pregnadien-21-oic acid (62358-12-7)

Guidance literature:

With 7,10-dimethyl-2,4-dioxo-2,3,4,10-tetrahydro-benzo[g]pteridine-8-carboxylic acid; In ethanol; for 0.5h; Irradiation; pH : 9-11; var. reag.: lumiflavin, 3-methyllumiflavin;

DOI:10.1016/S0040-4039(00)98908-1

upstream raw materials:

prednisolon

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

Downstream raw materials:

methyl 17,20α-acetonidodihydroprednisolonate

Refernces

• 1、 -. "Anti-inflammatory carboxy pregnane derivatives". . . Retrieved 2008/06/13.
• 2、 Jasiczak, J.,Smoczkiewicz, M. A.. "OXIDATION OF CORTICOSTEROIDS BY FLAVINS". . p. 5221 - 5224. Retrieved 2007/10/02.