110536-31-7

Basic information

• Product Name: 22-fluorovitamin D3
• Synonyms: 22-fluorovitamin D3
• CAS NO: 110536-31-7
• Molecular Formula: C₂₇H₄₃FO
• Molecular Weight: 402.63
• Mol File: 110536-31-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 505.3°C at 760 mmHg
• Flash Point: 311.8°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 2.51E-12mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: 22-fluorovitamin D3(CAS DataBase Reference)
• NIST Chemistry Reference: 22-fluorovitamin D3(110536-31-7)
• EPA Substance Registry System: 22-fluorovitamin D3(110536-31-7)

Safety Data

• Hazardous Substances Data: 110536-31-7(Hazardous Substances Data)

Usage

Also Known As

1α,25-dihydroxy-22-fluorocholecalciferol

Type

Synthetic vitamin D analog

Purpose

Developed for potential use in treating calcium-related disorders such as osteoporosis and hyperparathyroidism

Functionality

Designed to mimic the effects of natural vitamin D in the body

Target

Regulation of calcium and phosphorus levels

Effects

Potent effects on bone health and mineral metabolism

Potential

Promising candidate for developing new therapeutic agents in endocrinology and bone diseases

Research Status

Ongoing to better understand potential benefits and possible side effects in clinical use

InChI:InChI=1/C27H43FO/c1-18(2)8-15-26(28)20(4)24-13-14-25-21(7-6-16-27(24,25)5)10-11-22-17-23(29)12-9-19(22)3/h10-11,18,20,23-26,29H,3,6-9,12-17H2,1-2,4-5H3/b21-10+,22-11-/t20-,23+,24+,25-,26?,27+/m0/s1

Upstream product

• 110536-27-1 22-fluorocholest-5-en-3β-acetate 
• 54604-57-8 (22S)-cholest-5-ene-3β,22-diol 3β-acetate 
• 110536-29-3 22-fluorocholesta-5,7-dien-3β-ol 
• 17711-16-9 22-(S)-hydroxycholesterol 
• 110536-30-6 22-fluoroprevitamin D₃ 

Relevant articles and documents

THE SYNTHESIS AND BIOLOGICAL ACTIVITY OF 22-FLUOROVITAMINE D3: A NEW VITAMIN D ANALOG

We synthesized 22-fluorovitamin D3 from (22S) cholest-5-ene-3β,22-diol-3β-acetate 2.Compound 2 was treated with diethylaminosulfur trifluoride to give 22-fluorocholest-5-en-3β-acetate 3 and (E) 22-dehydrocholest-5-en-3β-acetate.Compound 3 was treated with N-bromosuccinimide to give a mixture of the respective 5,7- and 4,6-dienes.The 5,7-diene of 3 was separated from the 4,6-diene using the dienophile 4-phenyl-1,2,4-triazoline-3,5-dione. 22-Fluoro-5α,8α-(3,5-dioxo-4-phenyl-1,2,4-triazolino)-cholest-6-en-3β-acetate 4 was purified by flash chromatography and treated with lithium aluminium hydride to generate 22-fluorocholesta-5,7-dien-3β-ol 5.Photolysis of the diene 5, followed by thermal equilibration, resulted in the synthesis of 22-fluorovitamin D3 7.The vitamin 7 increased active intestinal calcium transport only at a dose of 50,000 pmol/rat, whereas vitamin D3 increased intestinal calcium transport at a dose of between 50 and 500 pmol/rat. 22-Fluorovitamin D3 7 did not mobilize bone and soft tissue calcium at a dose as high as 50,000 pmol/rat, whereas vitamin D3 was successful in doing so at a dose of 500 pmol/rat.When tested in the duodenal organ culture system, 22-fluorovitamin D3 7 had approximately 1/25th the potency of vitamin D3.It did not antagonize the activity of 1,25-dihydroxyvitamin D3. 22-Fluorovitamin D3 7 bound to the rat plasma vitamin D binding protein less avidly than vitamin D3. 22-Fluorovitamin D3 was bound very poorly to the chick intestinal cytosol receptor for 1,25-dihydroxyvitamin D3.We conclude that the introduction of fluorine at the C-22 position results in a vitamin D sterol with decreased biologic activity when compared to vitamin D3.The presence of a fluorine group at C-22 position inhibits the binding of the vitamin to rat vitamin D binding protein when compared to the binding of its hydrogen analog, vitamin D3.