13095-61-9

Basic information

• Product Name: cholest-5-ene-3 beta,26-diol
• Synonyms: Cholest-5-ene-3b,26-diol (8CI);26-Hydroxycholesterol; NSC 226105
• CAS NO: 13095-61-9
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 402.65
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 13095-61-9.mol
• Article Data: 26

Chemical Properties

• Melting Point: 170-175 °C
• Boiling Point: 517.1°Cat760mmHg
• Flash Point: 215.6°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 7.43E-13mmHg at 25°C
• Refractive Index: 1.537
• PKA: 15.03±0.70(Predicted)
• CAS DataBase Reference: cholest-5-ene-3 beta,26-diol(CAS DataBase Reference)
• NIST Chemistry Reference: cholest-5-ene-3 beta,26-diol(13095-61-9)
• EPA Substance Registry System: cholest-5-ene-3 beta,26-diol(13095-61-9)

Safety Data

• Hazardous Substances Data: 13095-61-9(Hazardous Substances Data)

Usage

Uses

26-Hydroxycholesterol is a desmosterol metabolite that is found in the brain. 26-Hydroxycholesterol has been used as a biomarker for carbon cycling in the northwestern Mediterranean Sea.

Definition

ChEBI: An oxysterol that is cholesterol substituted at position 26 by a hydroxy group.

InChI:InChI=1/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3

Upstream product

• 7554-95-2 kryptogenin diacetate 
• 13095-61-9 26-hydroxycholesterol 
• 71472-90-7 (25R)-3β.26-Dibenzoyloxy-5-cholesten-16-on 
• 79045-93-5 3β,26-dibezoyloxycholest-5-ene-16β-ol mesylate 
• 101978-09-0 (2R,6R)-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-heptan-1-ol 
• 43204-21-3 (20R,25R)-cholest-5-ene-3β,26-diol 3,26-diacetate 
• 77611-30-4 (25R)-26-hydroxy-16-oxocholesterol 
• 468-99-5 kryptogenin 
• 122682-91-1 (25R)-3β,26-bis[(tert-butyldimethylsilyl)oxy]-cholest-5-en-16β-ol 
• 31327-56-7 (25R)-cholest-5-ene-3β,16β,26-triol 
• 512-06-1 yamogenin 
• 1097641-33-2 (25S)-3β-(tert-butyldimethylsilyloxy)-26-(pivaloyloxy)cholest-5-ene 
• 1097641-43-4 (25S)-26-(pivaloyloxy)cholest-5-en-3β-ol 
• 79190-28-6 3β-(Tetrahydropyranyloxy)-23-(tosyloxy)-24-norchol-5-ene 

Downstream Products

• 113917-70-7 C₄₇H₆₀F₆O₆ 
• 13095-61-9 (25R)-cholest-5-ene-3β,26-diol 
• 894357-60-9 2,2-Dimethyl-propionic acid (2R,6R)-6-{(3R,5S,8R,9S,10S,13R,14S,17R)-3-[2-(4-benzoyl-phenyl)-acetoxy]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-2-methyl-heptyl ester 
• 949004-12-0 (25S)-3-keto-5α-cholest-7-en-26-oic acid 
• 148988-28-7 3β,27-dihydoxycholest-5-en-7-one 
• 481-21-0 cholestane 
• 113917-72-9 (25S)-3-acetoxy-26-tosyloxycholest-5-ene 
• 105078-98-6 (25S)-3β-acetoxy-26-trityloxycholest-5-ene 
• 105078-99-7 3-O-acetyl-26-hydroxy-26-O-tosylcholesterol 
• 192187-67-0 (25R)-7α,26-dihydroxycholest-4-en-3-one 
• 306288-45-9 (25R)-cholest-5-ene-3β,7α,26-triol 3β,26-dibenzoate 
• 306288-42-6 (25R)-7-oxocholest-5-en-3β,26-diyl dibenzoate 
• 392322-50-8 Toluene-4-sulfonic acid (2R,6R)-6-[(3S,9S,10R,13R,14R,17R)-3-(tert-butyl-dimethyl-silanyloxy)-4,4,10,13-tetramethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-heptyl ester 
• 250257-07-9 (25R)-(26-tosyloxy)-4,4-dimethyl-5α-cholesta-8,14-diene-3β-ol 

Relevant articles and documents

Enzymatic transesterification of steroid esters in organic solvents

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Structural and biochemical characterization of Mycobacterium tuberculosis CYP142: Evidence for multiple cholesterol 27-hydroxylase activities in a human pathogen

The Mycobacterium tuberculosis cytochrome P450 enzyme CYP142 is encoded in a large gene cluster involved in metabolism of host cholesterol. CYP142 was expressed and purified as a soluble, low spin P450 hemoprotein. CYP142 binds tightly to cholesterol and its oxidized derivative cholest-4-en-3-one, with extensive shift of the heme iron to the high spin state. High affinity for azole antibiotics was demonstrated, highlighting their therapeutic potential. CYP142 catalyzes either 27-hydroxylation of cholesterol/cholest-4-en-3-one or generates 5-cholestenoic acid/cholest-4-en-3-one-27-oic acid from these substrates by successive sterol oxidations, with the catalytic outcome dependent on the redox partner system used. The CYP142 crystal structure was solved to 1.6 A, revealing a similar active site organization to the cholesterol-metabolizing M. tuberculosis CYP125, but having a near-identical organization of distal pocket residues to the branched fatty acid oxidizing M. tuberculosis CYP124. The cholesterol oxidizing activity of CYP142 provides an explanation for previous findings that ΔCYP125 strains of Mycobacterium bovis and M. bovis BCG cannot grow on cholesterol, because these strains have a defective CYP142 gene. CYP142 is revealed as a cholesterol 27-oxidase with likely roles in host response modulation and cholesterol metabolism.

PEPTIDES

The present invention relates to dual-site BACE1 inhibitors, their manufacture, pharmaceutical compositions containing them and their use as therapeutically active substances. The active compounds of the present invention are useful in the therapeutic and/or prophylactic treatment of e.g. Alzheimer's disease.

Stereoselective synthesis and hormonal activity of novel dafachronic acids and naturally occurring steroids isolated from corals

A stereoselective synthesis of (25S)-Δ1-, (25S)-Δ1,4-, (25S)-Δ1,7-, (25S)- Δ8(14)-, (25S)-Δ4,6,8(14)-dafachronic acid, methyl (25S)-Δ1,4-dafachronate and (25S)-5α-hydroxy-3,6- dioxocholest-7-en-26-oic acid is described. (25S)-Δ1,4- Dafachronic acid and its methyl ester are natural products isolated from corals and have been obtained by synthesis for the first time. (25S)-5α-Hydroxy- 3,6-dioxocholest-7-en-26-oic acid represents a promising synthetic precursor for cytotoxic marine steroids.