13951-70-7

Basic information

• Product Name: 11a,16b,17,21-Tetrahydroxy-pregna-1,4-diene-3,20-dione
• Synonyms: 11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione;16 Alpha Hydroxprednisolone;16A-HYDROXY-PREDNISONLONE;16α-HYDROXY-PREDNISONLONE;11,16a,17a,21-Tetrahydroxypregna-1,4-diene-3,20-dione;11β,16α,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione;11β,16α,17α,21-Tetrahydroxypregna-1,4-diene-3,20-dione;Einecs 237-731-1
• CAS NO: 13951-70-7
• Molecular Formula: C₂₁H₂₈O₆
• Molecular Weight: 376.44
• EINECS: 237-731-1
• Product Categories: Pharmaceutical Raw Materials;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;Steroids;Metabolites & Impurities
• Mol File: 13951-70-7.mol

Chemical Properties

• Melting Point: 235-238°C
• Boiling Point: 591.5 °C at 760 mmHg
• Flash Point: 325.6 °C
• Appearance: white crystalline solid
• Density: 1.381 g/cm³
• Vapor Pressure: 1.86E-16mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 11.93±0.70(Predicted)
• Water Solubility: 815mg/L at 20℃
• CAS DataBase Reference: 11a,16b,17,21-Tetrahydroxy-pregna-1,4-diene-3,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 11a,16b,17,21-Tetrahydroxy-pregna-1,4-diene-3,20-dione(13951-70-7)
• EPA Substance Registry System: 11a,16b,17,21-Tetrahydroxy-pregna-1,4-diene-3,20-dione(13951-70-7)

Safety Data

• Hazardous Substances Data: 13951-70-7(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 13951-70-7 differently. You can refer to the following data:
1. A metabolite of Budesonide, an antiinflammatory agent
2. A metabolite of Budesonide (B689490), an antiinflammatory agent.
3. 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.

InChI:InChI=1/C21H28O6/c1-19-6-5-12(23)7-11(19)3-4-13-14-8-16(25)21(27,17(26)10-22)20(14,2)9-15(24)18(13)19/h5-7,13-16,18,22,24-25,27H,3-4,8-10H2,1-2H3

Upstream product

• 3044-42-6 21-acetoxy-11β-hydroxyl-1,4,16-pregnatriene-3,20-dione 
• 50-24-8 prednisolon 
• 64945-47-7 21-acetoxy-17α-hydroxy-11β-trifluoroacetoxy-1,4-pregnadiene-3,20-dione 
• 52-21-1 prednisolone 21-acetate 
• 37413-91-5 2-((10S,13S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate 
• 3103-17-1 17α-dehydroxyprednisolone 
• 98422-55-0 16α-21-diacetoxyprednisolone 
• 86401-80-1 11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate 
• 91160-89-3 9α-bromo-11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate 
• 77017-20-0 16α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione-21-acetate 
• 37413-91-5 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate 
• 1171-81-9 11β,16α,17,21-tetrahydroxy-pregn-4-ene-3,20-dione 

Downstream Products

• 1185143-77-4 S-{[(4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-8-(2-fluoro-4-methoxyphenyl)-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6b-yl]carbonyl} dimethylthiocarbamate 
• 1185143-78-5 (4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-8-(2-fluoro-4-methoxyphenyl)-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxole-6b-carboxylic acid 

Relevant articles and documents

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The invention provides a preparation method and application of a 16, 17-dihydroxy steroid compound, and relates to the technical field of chemical synthesis. The method comprises the steps of: (a) reacting a compound shown as a formula I, lewis acid and an azole compound to obtain a compound shown as a formula II; and (b) reacting the compound as shown in the formula II, cyclic acyl peroxide and water, and then hydrolyzing under an alkaline condition to obtain a compound as shown in a formula III. Lewis acid and an azole compound are used in the dehydration reaction of the compound shown in the formula I, the operation is easy, the reaction conditions are mild, the energy cost is low, and the safety coefficient is high. The cyclic acyl peroxide is used in the oxidation reaction of the compound shown in the formula II, so that the method is good in atom economy, few in side reaction, free of excessive impurities, easy to implement and repeat, free of heavy metal participation, green, environment-friendly, safer and good in application prospect.

Preparation method of budesonide

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9-site dehalogenation method of steroid compound

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Preparation method of high-purity 16 alpha-hydroxyprednisolone

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Method for preparing 16 alpha-hydroxyprednisolone

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Preparation method of 16a-prednisolone hydroxyacetate

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A budesonide industrial preparation method (by machine translation)

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Method for preparing 16a-hydroxy prednisolone

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Method for preparing 16a, 21-diacetoxyprednisolone product

The invention provides a method for preparing a 16a, 21-diacetoxyprednisolone product. The method comprises that 17a-dehydroxyprednisolone as a raw material and an organic peroxyacid undergo an epoxidation reaction at the 16th and 17th in a first organic solvent to produce an epoxy, the epoxy and glacial acetic acid undergo a ring opening reaction in a second organic solvent in the presence of anacid catalyst to produce a desired product 16a, 21-diacetoxyprednisolone, and the crude 16a, 21-diacetoxyprednisolone is subjected to heating reflux in C1-4 lower alcohol so that the 16a, 21-diacetoxyprednisolone is decolorized and recrystallized and a 16a, 21-diacetoxyprednisolone product is obtained. The method is efficient and environmentally friendly, realizes a low cost and can prepare the 16a-hydroxyprednisolone intermediate 16a, 21-diacetoxyprednisolone.