11beta-Hydroxyboldione

Base Information

• Chemical Name: 11beta-Hydroxyboldione
• CAS No.: 898-84-0
• Molecular Formula: C19H24O3
• Molecular Weight: 300.398
• European Community (EC) Number: 635-887-9
• UNII: 5716EN1N08
• DSSTox Substance ID: DTXSID20432127
• Nikkaji Number: J2.785.901A
• Wikidata: Q76414666
• Mol file: 898-84-0.mol

Synonyms:11beta-Hydroxyboldione;898-84-0;Kurchinin, (11S)-;11beta-hydroxyandrosta-1,4-diene-3,17-dione;5716EN1N08;1,4-Androstadien-11beta-ol-3,17-dione;11beta-Hydroxyboldione, (+)-;UNII-5716EN1N08;(8S,9S,10R,11S,13S,14S)-11-hydroxy-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione;11beta-Hydroxyandrosta-1,4-dien-3,17-dione;Androsta-1,4-diene-3,17-dione, 11beta-hydroxy-;Androsta-1,4-diene-3,17-dione, 11-hydroxy-, (11beta)-;1,4-Androstadien-11-beta-ol-3,17-dione;11|A-Hydroxyboldione;11 beta -Hydroxyboldione;SCHEMBL4263827;11.BETA.-HYDROXYBOLDIONE;DTXSID20432127;11.BETA.-HYDROXYBOLDIONE, (+)-;1,4-ANDROSTADIEN-11.BETA.-OL-3,17-DIONE;(11beta)-11-Hydroxyandrosta-1,4-diene-3,17-dione;11.BETA.-HYDROXYANDROSTA-1,4-DIEN-3,17-DIONE;11.BETA.-HYDROXYANDROSTA-1,4-DIENE-3,17-DIONE;ANDROSTA-1,4-DIENE-3,17-DIONE, 11.BETA.-HYDROXY-;11beta-Hydroxyandrosta-1,4-dien-3,17-dione (11beta-Hydroxyboldione);ANDROSTA-1,4-DIENE-3,17-DIONE, 11-HYDROXY-, (11.BETA.)-;(11beta)-11-Hydroxy-androsta-1,4-diene-3,17-dione;Androsta-1,4-diene-3,17-dione, 11beta-hydroxy- (6CI,7CI,8CI);11beta-Hydroxyandrosta-1,4-diene-3,17-dione

Chemical Property of 11beta-Hydroxyboldione

Chemical Property:

• PSA: 54.37000
• LogP: 2.83420
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 300.17254462
• Heavy Atom Count: 22
• Complexity: 616

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Hazard Codes: T
• Statements: 45-46-36/37/38
• Safety Statements: 53-22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC(C3C(C1CCC2=O)CCC4=CC(=O)C=CC34C)O
• Isomeric SMILES: C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=O)C=C[C@]34C)O
• Uses: 11β-Hydroxyboldione is the photochemical derivative of Prednisolone (P703740), synthetic corticosteroid that is metabolically interconvertible with prednisone (P703780).

Technology Process of 11beta-Hydroxyboldione

There total 25 articles about 11beta-Hydroxyboldione 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: 87.0%

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)

Guidance literature:

In water; acetonitrile; at 20 ℃; Electrochemical reaction;

DOI:10.1002/chem.202100446

Reference yield: 80.0%

→ (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)

Guidance literature:

With tert-butyldimethylsilyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 0 - 20 ℃; for 2h;

Reference yield: 79.1%

C19H23BrO3 → (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)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; at 15 ℃; for 3h; Reagent/catalyst; Inert atmosphere;

upstream raw materials:

prednisolon

methanol

17α-benzoyloxy-11β,21,21-trihydroxy-1,4-pregnadien-3-one hydrate

Androsta-1,4-diene-3,17-dione

Downstream raw materials:

17α-cyano-17β-acetoxy-11β-hydroxy-1,4-androstadien-3-one

17β-cyano-17α-acetoxy-11β-hydroxy-1,4-androstadiene

Acetic acid (8S,9S,10R,11S,13S,14S,17S)-11-acetoxy-17-cyano-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester

17β-cyano-11β,17α-diacetoxy-1,4-androstadien-3-one

Refernces

• 1、 DellaGreca, Marina,Fiorentino, Antonio,Isidori, Marina,Lavorgna, Margherita,Previtera, Lucio,Rubino, Maria,Temussi, Fabio. "Toxicity of prednisolone, dexamethasone and their photochemical derivatives on aquatic organisms". . p. 629 - 637. Retrieved 2004.
• 2、 Sommer, Florian,Kappe, C. Oliver,Cantillo, David. "Electrochemically Enabled One-Pot Multistep Synthesis of C19 Androgen Steroids". supporting information. p. 6044 - 6049. Retrieved 2021/03/15.
• 3、 -. "HYDROXYSTEROID COMPOUNDS, THEIR INTERMEDIATES, PROCESS OF PREPARATION, COMPOSITION AND USES THEREOF". Page/Page column 48. . Retrieved 2016/02/09.