7alpha,25-Dihydroxycholesterol

Base Information

• Chemical Name: 7alpha,25-Dihydroxycholesterol
• CAS No.: 64907-22-8
• Molecular Formula: C27H46 O3
• Molecular Weight: 418.66
• ChEMBL ID: CHEMBL4788348
• DSSTox Substance ID: DTXSID001311434
• Metabolomics Workbench ID: 36830
• Nikkaji Number: J652.922D
• Wikidata: Q27074018
• Mol file: 64907-22-8.mol

Synonyms:7,25-dihydroxycholesterol;7,25-dihydroxycholesterol, (3beta,7alpha)-isomer;7,25-dihydroxycholesterol, (3beta,7beta)-isomer;7,25-OHC

Chemical Property of 7alpha,25-Dihydroxycholesterol

Chemical Property:

• PSA: 60.69000
• LogP: 5.47440
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble5mg/mL (clear solution)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 418.34469533
• Heavy Atom Count: 30
• Complexity: 669

Purity/Quality:

97% ^*data from raw suppliers

3β,7α,25-Trihydroxycholest-5-ene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)O)C
• Isomeric SMILES: C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O)C
• Uses: 3β,7α,25-Trihydroxycholest-5-ene is a potent agonist of GPR183 that induces specific activation of the receptor. GPR183 (also known as Epstein-Barr virus-induced gene 2) is an orphan G protein-coupled receptor (GPCR) that is highly expressed in spleen and is required for humoral immune responses, including B cell migration and T cell-dependent antibody production. 7α,25-dihydroxy Cholesterol (7α,25-DHC) is a potent agonist of GPR183 that induces specific activation of the receptor with an EC50 value of 50 nM (Kd = 450 pM). At concentrations below 3 μM, it does not show any appreciable binding activity when tested against eight different nuclear hormone receptors including LXR and thirty-one different G protein-coupled receptors in a panel of reporter gene assays. 7α,25-DHC can act as a potent chemokine, affecting migration of immune cells expressing GPR183 both in vitro (EC50 = 500 pM) and in vivo.[Cayman Chemical] 7α,25-dihydroxycholesterol has been used:as a G-protein-coupled receptor 183 ( GPR183) ligand in chemotaxis assay and intracellular cytokine staining method and in fluorescence-activated cell sorting (FACS) analysis of natural killer cells in oxysterol based calcium mobilization assay in Chinese hamster ovary (CHO) cells in competitive radioligand binding assay of Epstein-Barr virus-induced gene 2 (EBI2) expressing COS-7 cells

Technology Process of 7alpha,25-Dihydroxycholesterol

There total 6 articles about 7alpha,25-Dihydroxycholesterol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

cholest-5-ene-3β,7α,25-triol 3β,25-dibenzoate (306288-44-8) → [3H]-7alpha, 25-Dihydroxycholesterol (64907-22-8)

Guidance literature:

With methanol; potassium hydroxide; for 4h; Reflux; Inert atmosphere;

DOI:10.1016/j.bmcl.2016.09.029

Reference yield:

25-hydroxychlolesterol (2140-46-7) → [3H]-7alpha, 25-Dihydroxycholesterol (64907-22-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / pyridine / 3 h / 20 °C

2: 87 percent / PCC; 3A molecular sieves / benzene / 24 h / Heating

3: 71 percent / L-Selectride / tetrahydrofuran / 5 h / -78 °C

4: 51 percent / KOH / methanol / 1 h / Heating

With pyridine; potassium hydroxide; 3 A molecular sieve; L-Selectride; pyridinium chlorochromate; In tetrahydrofuran; methanol; benzene;

DOI:10.1016/S0039-128X(00)00131-8

Reference yield:

cholest-5-ene-3β,25-diol 3β,25-dibenzoate (64164-61-0) → [3H]-7alpha, 25-Dihydroxycholesterol (64907-22-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / PCC; 3A molecular sieves / benzene / 24 h / Heating

2: 71 percent / L-Selectride / tetrahydrofuran / 5 h / -78 °C

3: 51 percent / KOH / methanol / 1 h / Heating

With potassium hydroxide; 3 A molecular sieve; L-Selectride; pyridinium chlorochromate; In tetrahydrofuran; methanol; benzene;

DOI:10.1016/S0039-128X(00)00131-8

upstream raw materials:

cholest-5-ene-3β,7α,25-triol 3β,25-dibenzoate

25-hydroxychlolesterol

cholest-5-ene-3β,25-diol 3β,25-dibenzoate

3β,25-dihydroxycholest-5-en-7-one 3β,25-dibenzoate