11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione CAS 13951-70-7

Introduction：Basic information about 11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione CAS 13951-70-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Basic information

• Product Name: 11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione
• Synonyms: 16A-HYDROXY-PREDNISONLONE;11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione;16 Alpha Hydroxprednisolone;11,16a,17a,21-Tetrahydroxypregna-1,4-diene-3,20-dione;11β,16α,17α,21-Tetrahydroxypregna-1,4-diene-3,20-dione;Einecs 237-731-1;16-ALPHA-HYDROXY PREDNISOLONE;16A-HYDROXY-PREDNISOLONE
• CAS: 13951-70-7
• MF: C21H28O6
• MW: 376.44
• EINECS: 237-731-1
• Product Categories: Pharmaceutical Raw Materials;Metabolites & Impurities;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;Steroids;13951-70-7
• Mol File: 13951-70-7.mol

11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Chemical Properties

• Melting point: 235-238°C
• Boiling point: 591.5±50.0 °C(Predicted)
• density: 1.38±0.1 g/cm3(Predicted)
• vapor pressure: 0Pa at 25℃
• storage temp.: Sealed in dry,2-8°C
• solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• pka: 11.93±0.70(Predicted)
• form: Solid
• color: White to Light Yellow
• Water Solubility: 815mg/L at 20℃
• Major Application: pharmaceutical
• InChIKey: SEKYBDYVXDAYPY-WVOWJGHQNA-N
• SMILES: [C@@]12([H])C[C@@H](O)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@]1([H])[C@@]3(C)C=CC(=O)C=C3CC[C@@]21[H] |&1:0,3,5,11,14,16,18,28,r|
• LogP: 0.8 at 25℃
• CAS DataBase Reference: 13951-70-7(CAS DataBase Reference)

Safety Information

• WGK Germany: WGK 3
• Storage Class: 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
• Hazard Classifications: Repr. 1B

11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Usage And Synthesis

Related substances

Prednisolone is a synthetic adrenocortical steroid drug with predominantly glucocorticoid properties.

Chemical Properties

White Crystalline Solid

Uses

A metabolite of Budesonide (B689490), an antiinflammatory agent.

Uses

11β,16α,17α,21-Tetrahydroxypregna-1,4-diene-3,20-dione (Budesonide EP Impurity A) is a metabolite of Budesonide (B689490), an anti-inflammatory agent.

Synthesis

501 g of crude 16α-hydroxy prednisolone acetate is dissolved in 700 ml of dichloromethane and 700 ml of ethanol, then 1.5 ml of formic acid is added, 24 ml of 5% sodium hypochlorite aqueous solution is added dropwise, and the temperature is controlled at 15 °C, and the reaction is stirred to obtain the preliminary processed product; Add 150 ml of 5% sodium bisulfite aqueous solution to the above-mentioned preliminary treatment product, concentrate on removing the solvent, adding water to hydrolyze, and filter to obtain 45 g of 16α-hydroxyprednisolone acetate refined product; 45 g of 16α-hydroxyprednisolone acetate obtained above was dissolved in a mixed organic solvent of 250 ml of dichloromethane and 250 ml of methanol, stirred and cooled to 0 °C, 90 ml of 10% sodium sulfite aqueous solution was added, and the reaction was stirred. After completion, it was neutralized with 15% sulfuric acid by mass concentration; the mixed organic solvent was concentrated, watered out, filtered, and dried to obtain 36.5 g of 16α-hydroxyprednisolone (11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione).

References

[1] Patent: WO2016/120891, 2016, A1. Location in patent: Page/Page column 13; 14

11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Preparation Products And Raw materials

• Raw materials: Methanol-->Sodium hydroxide-->112,21-dihydroxypregna-1,4,16-triene-3,20-dione-->Dichloromethane-->16alpha-Hydroxyprednisonlone acetate
• Preparation Products: Desonide