64164-45-0

Basic information

• Product Name: 25-fluorocholesterol
• Synonyms: 25-fluorocholesterol
• CAS NO: 64164-45-0
• Molecular Formula: C₂₇H₄₅FO
• Molecular Weight: 404.64
• Mol File: 64164-45-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 489.4°C at 760 mmHg
• Flash Point: 305.3°C
• Appearance: /
• Density: 1.02g/cm³
• Vapor Pressure: 1.24E-11mmHg at 25°C
• Refractive Index: 1.518
• PKA: 15.03±0.70(Predicted)
• CAS DataBase Reference: 25-fluorocholesterol(CAS DataBase Reference)
• NIST Chemistry Reference: 25-fluorocholesterol(64164-45-0)
• EPA Substance Registry System: 25-fluorocholesterol(64164-45-0)

Safety Data

• Hazardous Substances Data: 64164-45-0(Hazardous Substances Data)

Usage

Nature

Synthetic derivative of cholesterol

Chemical Modification

Contains a fluorine atom at the 25-position

Application

Radiotracer in positron emission tomography (PET) imaging

Purpose

Study cholesterol metabolism and distribution in the body

Use in Disease Research

Assesses cholesterol uptake and storage in tissues
Particularly relevant to diseases such as atherosclerosis and other cardiovascular conditions

Role in Research

Studies the role of cholesterol in physiological and pathological processes

Significance

Important tool for understanding cholesterol metabolism in the body
Helps comprehend implications for health and disease

InChI:InChI=1/C27H45FO/c1-18(7-6-14-25(2,3)28)22-10-11-23-21-9-8-19-17-20(29)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1

Upstream product

• 53139-49-4 6β-methoxy-3α,5-cyclocholestan-25-ol 
• 69389-85-1 25-fluoro-6β-methoxy-3α,5-cyclo-5α-cholestane 
• 2140-46-7 25-hydroxychlolesterol 

Downstream Products

• 57-88-5 cholesterol 
• 313-04-2 demosterol 
• 474-62-4 Campesterol 
• 257939-67-6 24-ethylcholesterol 

Relevant articles and documents

Inhibitors of sterol synthesis. Effects of fluorine substitution at carbon atom 25 of cholesterol on its spectral and chromatographic properties and on 3-hydroxy-3-methylglutaryl coenzyme a reductase activity in CHO-K1 cells

25-Fluorocholesterol (III) was prepared by treatment of 25-hydroxycholesterol (IV) with hydrogen fluoride-pyridine. Compounds III, IV, and cholesterol (I) were fully characterized by 1H and 13C NMR, and stereochemical assignments were established for the C-22 and C-23 protons. The side-chain proton assignments, which apply to most other sterols with a saturated eight-carbon side chain, were based on conformational analysis and comparison with NMR data for 25,26,26,26,27,27,27-heptafluorocholesterol (II). The chromatographic behavior of I, II, and III were compared on thin-layer chromatography, high performance liquid chromatography, and gas chromatography. Major fragment ions in electron-impact mass spectra of III were analogous to ions of either cholesterol or desmosterol, and a similar analogy was observed for the trimethylsilyl ethers. The 25-hydroxysterol IV and the 25-fluorosterol III differed markedly in their effects on the levels of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in CHO-K1 cells. Whereas 25-hydroxycholesterol caused a ～66% lowering of reductase activity in cells at 0.1 ·M, the 25-fluorosterol III had no effect at this concentration.

Blocked cholecalciferol and dihydrotachysterol 3 derivatives

Novel cholecalciferol and dihydrotachysterol3 derivatives produced against metabolic conversions at the 25-position, their preparation, pharmaceutical compositions, methods of treating steroid-induced osteoporosis, senile osteoporosis and secondary hyperparathyroidism, especially that induced by an insufficient amount of calcium in relationship to the amount of phosphate, novel intermediates and their preparation are disclosed.