51372-29-3

Basic information

• Product Name: 16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione
• Synonyms: 16a(r),17-(butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione;(r)-budesonide;(22R)-Budesonide;16α,17-[(R)-Butylidenebisoxy]-11β,21-dihydroxypregna-1,4-diene-3,20-dione;(22R)-Budesonide (>90% de);Dexbudesonide;(11β,16α)-;TriaMcinolone-d5
• CAS NO: 51372-29-3
• Molecular Formula: C₂₅H₃₄O₆
• Molecular Weight: 430.53
• EINECS: 257-161-7
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 51372-29-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 194-199°C
• Boiling Point: 599.7 °C at 760 mmHg
• Flash Point: 201.8 °C
• Appearance: light beige solid
• Density: 1.27 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly, Heated)
• PKA: 12.87±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione(51372-29-3)
• EPA Substance Registry System: 16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione(51372-29-3)

Safety Data

• Hazardous Substances Data: 51372-29-3(Hazardous Substances Data)

Usage

Description

16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione is a complex organic compound belonging to the class of steroids. It is characterized by its unique molecular structure, which includes a butylidenebis(oxy) bridge and multiple hydroxyl groups. 16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione is derived from the pregnane family of steroids, which are known for their diverse biological activities and potential applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione is used as a pharmaceutical compound for its potential therapeutic applications. 16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione's unique structure and functional groups may allow it to interact with various biological targets, making it a promising candidate for the development of new drugs.
Used in Steroid Research:
In the field of steroid research, 16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione can be used as a starting material or a reference compound for the synthesis and evaluation of novel steroidal compounds. Its structural features may provide insights into the design and optimization of new steroids with improved pharmacological properties.
Used in Drug Delivery Systems:
Similar to gallotannin, 16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione may also be employed in the development of drug delivery systems. Its unique structural features could be utilized to improve the solubility, stability, and bioavailability of other drugs, potentially enhancing their therapeutic efficacy.
Used in Budesonide (B689490) Epimer R:
16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione is used as a key intermediate in the synthesis of Budesonide (B689490) epimer R. Budesonide is a glucocorticoid with anti-inflammatory properties, used in the treatment of various inflammatory conditions, such as asthma and allergies.
Used in Labelled Triamcinolone:
16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione can also be used in the preparation of labelled Triamcinolone, a glucocorticoid with antiasthmatic and antiallergic properties. Labelled Triamcinolone can be employed in research and diagnostic applications, such as tracking the distribution and metabolism of the drug in the body.
Chemical Properties:
16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione is a light beige solid, indicating its stability and suitability for various pharmaceutical applications. Its solid-state properties may also influence its formulation and delivery in drug development.

InChI:InChI=1/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21+,22+,23-,24-,25+/m0/s1

Upstream product

• 51333-05-2 2-((6aR,6bS,7S,8aS,8bS,11aR,12aS,12bS)-7-hydroxy-6a,8a-dimethyl-4-oxo-10-propyl-2,4,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-8b-yl)-2-oxoethyl acetate 
• 13951-70-7 desonide 
• 123-72-8 butyraldehyde 
• 638-94-8 desonide 
• 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 
• 77017-20-0 16α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione-21-acetate 
• 91160-89-3 9α-bromo-11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate 
• 52-21-1 prednisolone 21-acetate 
• 64945-47-7 21-acetoxy-17α-hydroxy-11β-trifluoroacetoxy-1,4-pregnadiene-3,20-dione 

Downstream Products

• 85234-63-5 21-dehydrobudesonide 
• 51372-28-2 (22S)-Budesonide 
• 1345092-51-4 C₃₃H₃₈O₈ 
• 1345092-15-0 C₃₆H₄₃NO₁₃ 
• 1345092-52-5 C₃₃H₄₀O₈ 
• 1345092-53-6 C₃₆H₄₃ClO₁₀ 
• 51333-05-2 2-((6aR,6bS,7S,8aS,8bS,11aR,12aS,12bS)-7-hydroxy-6a,8a-dimethyl-4-oxo-10-propyl-2,4,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-8b-yl)-2-oxoethyl acetate 

Relevant articles and documents

Preparation method of budesonide

The invention discloses a preparation method of budesonide, and belongs to the technical field of preparation and processing of medicines. According to the method, prednisolone acetate is used as an initial raw material, and is subjected to five steps of protection, dehydration, dihydroxy, hydrolysis and condensation to prepare the budesonide. According to the preparation method, the reaction process can be effectively shortened by improving the defects of a traditional process, reaction conditions are mild, osmium tetroxide which is high in toxicity and not environmentally friendly is avoided, environmental pollution is reduced, and the method is high in overall conversion rate, easy and convenient to operate, suitable for industrial production and wide in market prospect.

INDUSTRIAL ECOLOGICAL PROCESS OF MANUFACTURING OF BUDESONIDE

Disclosed herein is an improved process for the preparation of Budesonide using Perchloric acid catalyst in water as a major medium.

The preparation method of the budesonide

The invention discloses a preparation method of budesonide. The preparation method comprises the following steps: (1) carrying out n-butyraldehyde aldolization for 16 alpha-hydroxyl prednisolone acetate as shown in formula (1) to obtain a budesonide crude prodct; (2) then hydrolyzing 21-acetates; and (3) collecting the product budesonide from reactant. By adopting the preparation method, the unstable midbody 16 alpha-hydroxyl prednisolone is avoided. The preparation method is easy to operate and control, and the total yield of the budesonide is greatly increased. The reaction formula is shown in the specification.