244291-23-4

Basic information

• Product Name: 25-hydroxy-6-<3-(tetrahydro-2H-pyran-2-yloxy)propyl>vitamin D₃-acetate
• Synonyms: 25-hydroxy-6-<3-(tetrahydro-2H-pyran-2-yloxy)propyl>vitamin D₃-acetate
• CAS NO: 244291-23-4
• Molecular Weight: 584.88
• Mol File: 244291-23-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 25-hydroxy-6-<3-(tetrahydro-2H-pyran-2-yloxy)propyl>vitamin D₃-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 25-hydroxy-6-<3-(tetrahydro-2H-pyran-2-yloxy)propyl>vitamin D₃-acetate(244291-23-4)
• EPA Substance Registry System: 25-hydroxy-6-<3-(tetrahydro-2H-pyran-2-yloxy)propyl>vitamin D₃-acetate(244291-23-4)

Safety Data

• Hazardous Substances Data: 244291-23-4(Hazardous Substances Data)

Upstream product

• 244291-29-0 2-[(1R,3aS,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-1-((1R,5R)-2-methylene-bicyclo[3.1.0]hex-1-yl)-ethanone 
• 19356-17-3 calcidiol 
• 33821-94-2 3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide 
• 64-19-7 acetic acid 

Downstream Products

• 244291-26-7 Bromo-acetic acid 5-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-4-[(S)-5-hydroxy-2-methylene-cyclohex-(Z)-ylidene]-pentyl ester 
• 244291-40-5 Acetic acid (R)-3-hydroxy-5-[1-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-4-(tetrahydro-pyran-2-yloxy)-but-(Z)-ylidene]-4-methylene-cyclohexyl ester 
• 244291-33-6 25-hydroxy-6-<3-(2-tetrahydro-2H-pyran-2-yloxy)propyl>vitamin D₃ 

Relevant articles and documents

C-6 functionalized analogs of 25-hydroxyvitamin D3 and 1α,25- dihydroxyvitamin D3: Synthesis and binding analysis with vitamin D-binding protein and vitamin D receptor

In this article, we describe the development of a general synthetic strategy to functionalize the C-6 position of vitamin D3 and its biologically important metabolites, i.e. 25-hydroxyvitamin D3 (25-OH-D3) and 1α,25-dihydroxyvitamin D3 [1,25(OH)2D3]. We employed Mazur's cyclovitamin D method to synthesize vitamin D3 analogs with several functionalities at the C-6 position. In addition, we synthesized 6-(3- hydroxypropyl) and 6-[(2-bromoacetoxy)propyl] derivatives of 25-OH-D3 15 and 16, respectively, and 6-(3-hydroxypropyl) derivative of 1,25(OH)2D3 17. Competitive binding assays of 15-17 with human serum vitamin D-binding protein showed that all these analogs specifically bound to this protein, although with significantly lower affinity than the 25-OH-D3, the strongest natural binder, but with comparable affinity with 1,25(OH)2D3, the hormone. On the other hand, 6-[3-hydroxypropyl], 1α,25-dihydroxyvitamin D3 17 did not show any specific binding for recombinant nuclear vitamin D receptor. These results indicated that the region containing the C-6 position of the parent seco-steroid [l,25(OH)2D3] may be an important recognition marker towards vitamin D receptor binding. Information, delineated in this article, will be important for evaluating structure-activity relationship in synthetic analogs of vitamin D and its metabolites.