34310-88-8

Basic information

• Product Name: (3beta,5alpha,17xi)-cholest-6-ene-3,5-diol
• CAS NO: 34310-88-8
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 402.6529
• Mol File: 34310-88-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 500.3°C at 760 mmHg
• Flash Point: 206.8°C
• Density: 1.029g/cm³
• Vapor Pressure: 4.16E-12mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: (3beta,5alpha,17xi)-cholest-6-ene-3,5-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta,5alpha,17xi)-cholest-6-ene-3,5-diol(34310-88-8)
• EPA Substance Registry System: (3beta,5alpha,17xi)-cholest-6-ene-3,5-diol(34310-88-8)

Safety Data

• Hazardous Substances Data: 34310-88-8(Hazardous Substances Data)

Upstream product

• 19317-89-6 3β-acetoxycholest-6-en-5α-ol 
• 57-88-5 cholesterol 
• 55529-60-7 cholesterol 5α-hydroperoxide 
• 1250-95-9 5α,6α-epoxycholestan-3β-ol 
• 57566-18-4 7α-bromocholesterol acetate 

Downstream Products

• 566-93-8 cholesta-4,6-dien-3-one 

Relevant articles and documents

Photochemistry of bacteriochlorophylls in human blood plasma: 2. Reaction mechanism investigated by product analysis and deuterium isotope effect

Transmetalated (Pd) bacteriochlorophyll derivatives are currently being clinically tested as sensitizers for photodynamic therapy. Protocols using short delay times between injection and irradiation generate interest in the photochemistry of these pigments in the blood. Using near-infrared irradiation where these pigments absorb strongly, we have studied the mechanism of photo-oxidation in two lipoprotein fractions, low- and high-density lipoproteins, derived from human blood plasma that preferentially accumulate these pigments (Dandler et al. [2009] Photochem. Photobiol., 85, in press). Using quenchers of reactive oxygen species, and chemical reporters, in particular peroxides generated from cholesterol as an inherent component of the lipoproteins, a Type II mechanism generating singlet oxygen has been demonstrated for Pd- and Zn-bacteriopheophorbides. In homogeneous systems, accelerated bleaching in D2O, compared with H2O, supports this mechanism. An unusual deuterium isotope effect was observed, by contrast, in heterogeneous amphiphilic-water systems. In the early phase, and under high oxygen concentrations, again a positive D-isotope effect is observed which later, in a second phase, is reversed to a negative D-isotope effect. The latter cannot be explained by heterogeneous pigment populations in the amphiphilic system; we, therefore, conclude a mechanistic switch, and discuss a possible mechanism.

Singlet-oxygen ene reaction with 3β-substituted stigmastanes. An alternative pathway for the classical Schenck rearrangement

The course of the singlet-oxygen ene reaction with stigmasta-5,22-dienes may be controlled if in the substrate a good leaving group as substituent is present at 3-C. Thus when the 5α-hydroperoxystigmasta-5,22-diene is formed instead of the well known allylic rearrangement to yield the 7α-hydroperoxystigmasta-5,22-diene isomer an intramolecular nucleophilic substitution can then occur yielding 5α-hydroxystigmasta-6,22-dien-3-one. Various stigmasta-5,22-dienes were chosen to elucidate which feature of the stigmastane is necessary to control the course of the reaction. Thus, 3β-F, 3β-Cl, 3β-Br, 3β-I and 3α-Br-stigmasta-5,22-dienes were firstly prepared and fully characterized in order to study their reaction with 1O2 under different experimental conditions. 3β-Acetoxy- and 3β-mesyloxy-stigmasta-5,22-diene derivatives were also prepared and studied.

Photodynamically generated 3-beta-hydroxy-5alpha-cholest-6-ene-5-hydroperoxide: Toxic reactivity in membranes and susceptibility to enzymatic detoxification

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