86900-29-0

Basic information

• Product Name: 3β-hydroxycholest-5-ene-7-hydroperoxide
• Synonyms: 3β-hydroxycholest-5-ene-7-hydroperoxide
• CAS NO: 86900-29-0
• Molecular Weight: 418.66
• Mol File: 86900-29-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 3β-hydroxycholest-5-ene-7-hydroperoxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3β-hydroxycholest-5-ene-7-hydroperoxide(86900-29-0)
• EPA Substance Registry System: 3β-hydroxycholest-5-ene-7-hydroperoxide(86900-29-0)

Safety Data

• Hazardous Substances Data: 86900-29-0(Hazardous Substances Data)

Upstream product

• 57-88-5 cholesterol 
• 75-91-2 tert.-butylhydroperoxide 

Downstream Products

• 566-28-9 7-Oxocholesterol 
• 566-26-7 (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol 
• 566-27-8 cholest-5-en-3β,7β-diol 
• 33287-26-2 7β-hydroxy-cholesterol trimethylsilyl ether 
• 16840-37-2 7-hydroxycholesterol 
• 81739-28-8 C₂₇H₄₆O₂ 
• 116150-37-9 3β-hydroxy-cholest-5-en-7-one-(2,4-dinitro-phenylhydrazone) 
• 566-26-7 Cholest-5-ene-3α,7α-diol 

Relevant articles and documents

Synthesis of 7-hydroperoxycholesterol and its separation, identification, and quantification in cholesterol heated model systems

7-Hydroperoxycholesterol is considered to be an intermediate compound of the cholesterol oxidation path as the first product formed when cholesterol is oxidized by triplet oxygen. However, there is a limitation on cholesterol mechanism studies because of the lack of 7-hydroperoxycholesterol analytical standard due to its low stability. To verify the formation of hydroperoxides in cholesterol model systems heated at 140, 180, and 220 °C, 7α-hydroperoxycholesterol was synthesized by cholesterol photooxidation followed by rearrangement at room temperature in chloroform. Its structure was confirmed on the basis of 13C NMR and mass spectra obtained by APCI-LC-MS. The synthesized compound was also used as standard for the quantification of 7-hydroperoxycholesterol as the sum of 7α-and 7β-hydroperoxycholesterol. The results demonstrated that 7-hydroperoxycholesterol is the first compound formed when the temperature is lower (140 °C). However, the concentration of the 7-hydroperoxycholesterol depends on the temperature and time of exposure: the higher the time, the higher the amount of 7-hydroperoxycholesterol at lower temperatures, and the lower the time, the lower the amount of 7-hydroperoxycholesterol at higher temperatures (180 and 220 °C). By the formation of 7-hydroperoxycholesterol, the known cholesterol oxidation mechanism in three phases (initiation, propagation, and termination) could be confirmed; once at lower temperatures, the stage of cholesterol oxidation is at initiation, at which hydroperoxide formation predominates.

Cholesterol hydroperoxides generate singlet molecular oxygen [O 2(1Δg)]: Near-IR emission, 18O-labeled hydroperoxides, and mass spectrometry

In mammalian membranes, cholesterol is concentrated in lipid rafts. The generation of cholesterol hydroperoxides (ChOOHs) and their decomposition products induces various types of cell damage. The decomposition of some organic hydroperoxides into peroxyl

Synthesis, characterization, and electrochemical studies of new π-Extended metalloporphyrins

A doubly fused porphyrin has been synthesized by two successive cyclization reactions. The first meso-phenyl group was fused, by an intramolecular Cadogan reaction leading to an enamine-functionalized porphyrin. After Vilsmeier-Haack formylation of the ni