55529-60-7

Usage

InChI:InChI=1/C27H46O3/c1-18(2)7-6-8-19(3)22-9-10-23-21-12-16-27(30-29)17-20(28)11-15-26(27,5)24(21)13-14-25(22,23)4/h12,16,18-24,28-29H,6-11,13-15,17H2,1-5H3/t19-,20+,21+,22-,23+,24+,25-,26-,27+/m1/s1

Upstream product

• 110-86-1 pyridine 
• 57-88-5 cholesterol 
• 14459-29-1 hematoporphyrin 
• 517-10-2 allocholesterol 
• 34026-89-6 cholesterin 
• 57-88-5 cholesterol 

Downstream Products

• 16840-37-2 7-hydroxycholesterol 
• 566-28-9 7-Oxocholesterol 
• 1049736-05-1 C₃₁H₅₆O₄ 
• 1049736-07-3 C₃₁H₅₆O₄ 
• 81811-27-0 3β-hydroxy-5-oxo-5,6-secocholestan-6-al 
• 33287-26-2 7β-hydroxy-cholesterol trimethylsilyl ether 
• 566-27-8 cholest-5-en-3β,7β-diol 
• 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 
• 34310-88-8 3β,5α-dihydroxycholest-6-ene 

Relevant academic research and scientific papers

On the Products of Cholesterol Autoxidation in Phospholipid Bilayers and the Formation of Secosterols Derived Therefrom

In homogenous solution, cholesterol autoxidation leads to a mixture of epimers of 5 primary products, whose concentrations vary in the presence/absence of antioxidants, such as vitamin E. Two of the products (5α-OOH and 6β-OOH) undergo Hock fragmentation

Gadolinium(III) Porpholactones as Efficient and Robust Singlet Oxygen Photosensitizers

Construction of GdIIIphotosensitizers is important for designing theranostic agents owing to the unique properties arising from seven unpaired f electrons of the Gd3+ion. Combining these with the advantages of porpholactones with tun

Synthesis, Characterization, and Electronic Properties of Porphyrins Conjugated with N-Heterocyclic Carbene (NHC)-Gold(I) Complexes

Porphyrins fused to peripheral N-heterocyclic carbenes (NHC) across two neighboring β,β-pyrrolic positions were used for the synthesis of different mono- and bis-carbenic gold(I) complexes. These studies also revealed how it is possible to modulate the re

Comparison of photo-oxidation reactions in batch and a new photosensitizer-immobilized microfluidic device

A glass microfluidic device has been functionalized with photoactive porphyrins for performing reactions which are mediated by singlet molecular oxygen. The resulting device was used to investigate the photochemical oxidation of cholesterol, α-terpinene, and citronellol under flow conditions, and the results were compared with similar batch reactions.

A new approach to N-phenylquinolino[2,3,4-at]porphyrins: Electrochemical and photochemical studies

A new route to N-phenylquinolino[2,3,4-at]porphyrins is described and the electrochemical and photochemical properties of the synthesized derivatives were investigated. The electrochemical studies (cyclic voltammetry and rotating disk voltammetry) of the

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

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.

The ratio of cholesterol 5,6-secosterols formed from ozone and singlet oxygen offers insight into the oxidation of cholesterol in vivo

Ongoing efforts to unravel the origins of the cholesterol 5,6-secosterols (1a and 1b) in biological systems have revealed that the two known chemical routes to these oxysterols, ozonolysis of cholesterol (3) and Hock-cleavage of 5-α-hydroperoxycholesterol (4a), are distinguishable based upon the ratio of the hydrazone derivatives (2a and 2b) formed in each case and this ratio offers an insight into the chemical origin of the secosterols in vivo. The Royal Society of Chemistry 2009.

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

Locked π-expanded chlorins in two steps from simple tetraarylporphyrins

(Chemical Equation Presented) Upon tandem Reformatsky reaction, easily accessible porphyrinic ketones give "locked" chlorinic diester. Both ketones and diesters, as bases or palladium complexes, efficiently generate singlet dioxygen, as demonstrated by tr