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

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

Used in Environmental Science:
Cholest-5-ene-3 beta,26-diol is used as a biomarker for carbon cycling in the northwestern Mediterranean Sea. Its presence in the environment helps researchers understand the carbon cycle and its impact on the ecosystem.
Used in Neurobiology:
As a desmosterol metabolite found in the brain, cholest-5-ene-3 beta,26-diol may have potential applications in neurobiological research. Studying its role and interactions within the brain can provide insights into various neurological processes and disorders.
Used in Pharmaceutical Research:
Due to its unique structure and properties, cholest-5-ene-3 beta,26-diol may be a promising candidate for pharmaceutical research. Its ability to modulate biological processes could lead to the development of new drugs and therapies for various conditions.

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

• 77611-30-4 (25R)-26-hydroxy-16-oxocholesterol 
• 13095-61-9 5-Cholesten-3β,26-diol 
• 71472-88-3 3β,26-dibenzoyloxycholest-5-en-16β-ol 
• 192187-69-2 (25R)-3β,26-bis (tert-butyldimethylsilyloxy)-cholest-5-ene 
• 512-04-9 diosgenin 
• 79190-29-7 (3S,8S,9S,10R,13R,14S,17R)-17-((1R,5S)-6-tert-Butoxy-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]phenanthren-3-ol 
• 64907-38-6 3β-24-norchol-5-ene-3,23-diol 
• 869858-19-5 (25R)-24-phenylsulfonylcholest-5-en-3β,26-diol 26-(2'-tetrahydropyranyl) ether 
• 869858-15-1 24-norchol-5-en-3β-23-diol 23-tosylate 
• 869858-16-2 23-iodo-24-norchol-5-en-3β-ol 
• 869858-24-2 (25S)-cholest-5-en-3β,26-diol 26-(2'-tetrahydropyranyl) ether 
• 213828-18-3 2-[(R)-2-Benzenesulfonyl-4-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-ethoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-pentyl]-2-methyl-[1,3]dioxolane 
• 7494-34-0 27-nor-5-cholesten-3β-ol-25-one 
• 32557-11-2 (R)-6-((3S,8S,9S,10R,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptanal 

Downstream Products

• 13095-61-9 (25R)-cholest-5-ene-3β,26-diol 
• 113917-70-7 C₄₇H₆₀F₆O₆ 
• 79897-01-1 (25R)-cholest-5-ene-3β,26-diyl dibenzoate 
• 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 
• 113917-72-9 (25S)-3-acetoxy-26-tosyloxycholest-5-ene 
• 105078-98-6 (25S)-3β-acetoxy-26-trityloxycholest-5-ene 
• 113917-68-3 C₄₇H₆₀F₆O₆ 
• 113917-68-3 C₄₇H₆₀F₆O₆ 
• 148988-28-7 3β,27-dihydoxycholest-5-en-7-one 
• 19257-21-7 (25ξ)-26-hydroxycholest-4-en-3-one 
• 481-21-0 cholestane 
• 105078-99-7 3-O-acetyl-26-hydroxy-26-O-tosylcholesterol 
• 192187-67-0 (25R)-7α,26-dihydroxycholest-4-en-3-one 

Relevant articles and documents

Synthesis and biological activity of the (25R)-cholesten-26-oic acids - Ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans

We describe the stereoselective transformation of diosgenin (4a) to (25R)-Δ4-dafachronic acid (1a), (25R)-Δ7- dafachronic acid (2a), and (25R)-cholestenoic acid (3a), which represent potential ligands for the hormonal receptor DAF-12

Synthesis and hormonal activity of the (25s)-cholesten-26-oic acids -potent ligands for the daf-12 receptor in caenorhabditis elegans

Using a highly stereoselective Evans aldol reaction for the introduction of the stereogenic center at C-25, we describe an efficient synthesis of the orthogonally diprotected (25S)-26-hydroxycholesterol 11. In a few synthetic steps, this crucial intermediate 11 has been converted into the four (25S)-cholesten-26-oic acids 1-4, which have been obtained in 12-15 steps and 19-53% overall yield based on commercially available 3p-hydroxychol-5-en-24-oic acid (5). Our biological studies of the compounds 1-4 reveal that (25S)-Δ7-dafachronic acid (1) represents the most active steroidal ligand for the hormonal receptor DAF-12 in Caenorhabditis elegans. Moreover, the saturated (25S)-dafachronic acid (3) represents a new ligand for this receptor and the (25S)-steroidal acids are more active as compared to their corresponding (25R)-counterparts.

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.

Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ22 steroids

A synthetic route that utilizes a cross-metathesis reaction with Δ22 steroids has been developed to prepare sterols with varying C-27 side-chains. Natural sterols containing hydroxyl groups at the 25 and (25R)-26 positions were prepared. Enantiomers of cholesterol and (3β,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.

Inhibitory effect of oxygenated cholestan-3-ol derivatives on the growth of Mycobacterium tuberculosis

A variety of cholestan-3-ol derivatives, which are oxygenated at different positions of the steroid ring system, were prepared and tested for their inhibition of the Mycobacterium tuberculosis H37Rv strain. Several compounds showed significant antitubercular activities with MIC90 values in the range 4-8 μM and low or non-detectable toxicity against mammalian cells.

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.

Stereoselective synthesis of (25r)-dafachronic acids and (25R)-cholestenoic acid as potential ligands for the DAF-12 receptor in Caenorhabditis elegans

Commercially available diosgenin has been used as starting material for a highly efficient synthesis of (25R)-dafachronic acids and (25R)-cholestenoic acid, potential ligands for the receptor DAF-12 in the nematode Caenorhabditis elegans.

Stereoselective synthesis of the hormonally active (25S)- Δ7-dafachronic acid, (25S)-Δ4-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid

We report a stereoselective synthesis of the (25S)-cholestenoic-26-acids which are highly efficient ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans.

Synthesis of the aglycone of the shark repellent pavoninin-4 using remote functionalization

The aglycone of shark repellent pavoninin-4, (25R)-5α-cholestan- 3α,15α,26-triol 26-acetate 1a, was synthesized from (25R)-cholest-5-en-3β,-26-diol 4 (26-hydroxycholesterol) in eight steps in 18% overall yield. Breslow's remote functionalization strategy