36871-91-7

Basic information

• Product Name: (3beta,7beta,17xi)-7-hydroperoxycholest-5-en-3-ol
• CAS NO: 36871-91-7
• Molecular Formula: C₂₇H₄₆O₃
• Molecular Weight: 418.6523
• Mol File: 36871-91-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 534.2°C at 760 mmHg
• Flash Point: 276.8°C
• Density: 1.05g/cm³
• Vapor Pressure: 1.22E-13mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: (3beta,7beta,17xi)-7-hydroperoxycholest-5-en-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta,7beta,17xi)-7-hydroperoxycholest-5-en-3-ol(36871-91-7)
• EPA Substance Registry System: (3beta,7beta,17xi)-7-hydroperoxycholest-5-en-3-ol(36871-91-7)

Safety Data

• Hazardous Substances Data: 36871-91-7(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 
• 566-26-7 Cholest-5-ene-3α,7α-diol 
• 566-27-8 cholest-5-en-3β,7β-diol 
• 16840-37-2 7-hydroxycholesterol 
• 81739-28-8 C₂₇H₄₆O₂ 
• 116150-37-9 3β-hydroxy-cholest-5-en-7-one-(2,4-dinitro-phenylhydrazone) 

Relevant articles and documents

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

Allylic oxidations catalyzed by dirhodium caprolactamate via aqueous tert-butyl hydroperoxide: The role of the tert-butylperoxy radical

Dirhodium(II) caprolactamate exhibits optimal efficiency for the production of the tert-butylperoxy radical, which is a selective reagent for hydrogen atom abstraction. These oxidation reactions occur with aqueous tert-butyl hydroperoxide (TBHP) without rapid hydrolysis of the caprolactamate ligands on dirhodium. Allylic oxidations of enones yield the corresponding enedione in moderate to high yields, and applications include allylic oxidations of steroidal enones. Although methylene oxidation to a ketone is more effective, methyl oxidation to a carboxylic acid can also be achieved. The superior efficiency of dirhodium(II) caprolactamate as a catalyst for allylic oxidations by TBHP (mol % of catalyst, % conversion) is described in comparative studies with other metal catalysts that are also reported to be effective for allylic oxidations. That different catalysts produce essentially the same mixture of products with the same relative yields suggests that the catalyst is not involved in product-forming steps. Mechanistic implications arising from studies of allylic oxidation with enones provide new insights into factors that control product formation. A previously undisclosed disproportionation pathway, catalyzed by the tert-butoxy radical, of mixed peroxides for the formation of ketone products via allylic oxidation has been uncovered.

Catalysis of Ene Reactions by Lithium Perchlorate

The ene reaction of some allylic hydrocarbons, and the metallo-ene reaction of some allyltin compounds, with 1,3,4-triazoline-2,5-diones or with diethyl azodicarboxylate as enophiles, in diethyl ether are strongly catalysed by lithium perchlorate.Azobenzene, on the other hand, reacts slowly with alkyltin compounds, undergoing hydrostannation.The reaction of cholesterol or of tributylallyltin with singlet oxygen is subject to a smaller catalysis.