25-Hydroxycholest-5-en-3-ol

Base Information

• Chemical Name: 25-Hydroxycholest-5-en-3-ol
• CAS No.: 2140-46-7
• Molecular Formula: C27H46O2
• Molecular Weight: 402.661
• Hs Code.: 29062990
• Mol file: 2140-46-7.mol

Synonyms:25-Hydroxycholest-5-en-3-ol;5-cholestene-3beta-25-diol;cholest-5-en-3beta-25-diol;Cholest-5-ene-3-b,25-diol;cholest-5-ene-3beta-25-diol;Cholest-5-ene-3-beta,25-diol;(beta)-cholest-5-ene-3-25-diol

Chemical Property of 25-Hydroxycholest-5-en-3-ol

Chemical Property:

• Vapor Pressure: 1.13E-12mmHg at 25°C
• Melting Point: 177-179 °C
• Refractive Index: 1.538
• Boiling Point: 513.1 °C at 760 mmHg
• PKA: 15.03±0.70(Predicted)
• Flash Point: 213.5 °C
• PSA: 40.46000
• Density: 1.03g/cm³
• LogP: 6.50360
• Storage Temp.: -20°C
• Solubility.: chloroform: 50 mg/mL, clear, colorless to slightly yellow
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 402.349780706
• Heavy Atom Count: 29
• Complexity: 636

Purity/Quality:

98%,99%, ^*data from raw suppliers

25-HydroxyCholesterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-48
• Safety Statements: 26-36-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CCCC(C)(C)O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCCC(C)(C)O)[C@H]1CCC2[C@@]1(CCC3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
• Description: 25-hydroxy Cholesterol is an oxysterol. It is formed from cholesterol by cholesterol-25-hydroxylase, and its production can be induced by inflammation or infection. 25-hydroxy Cholesterol suppresses endogenous cholesterol synthesis by binding to insulin-induced gene (INSIG) proteins and preventing sterol regulatory element binding proteins (SREBPs) from being transported to the Golgi. It inhibits IgA class switching induced by LPS and various cytokines in B cells (IC50 = ~50 nM). 25-hydroxy Cholesterol inhibits replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Vero cells (EC50 = 3.675 μM) and reduces increases in viral protein production in infected Vero cells when used prior to infection. It reduces viral RNA loads in the lung and trachea in a mouse model of SARS-CoV-2 infection when administered at a dose of 100 mg/kg per day. Serum levels of 25-hydroxy cholesterol are increased in mice expressing human angiotensin-converting enzyme 2 (hACE2), the functional receptor for SARS-CoV-2, in a model of SARS-CoV-2 infection and in a patient with COVID-19, the primarily respiratory disease caused by SARS-CoV-2.
• Uses: An oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It induces apoptosis in human monocytic cell lines as well as induc ing apoptosis in CEM cells associated with negative regulation of c-Myc. An oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It induces apoptosis in human monocytic cell lines as well as inducing apoptosis in CEM cells associated with negative regulation of c-Myc. 25-Hydroxycholesterol was used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.

Technology Process of 25-Hydroxycholest-5-en-3-ol

There total 144 articles about 25-Hydroxycholest-5-en-3-ol 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: 97.0%

C29H47BrO3 (1572295-85-2) → 25-hydroxychlolesterol (2140-46-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 5 - 70 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.steroids.2014.02.002

Reference yield: 97.0%

25-hydroxycholesteryl acetate (10525-22-1) → 25-hydroxychlolesterol (2140-46-7)

Guidance literature:

With potassium carbonate; In methanol; water;

DOI:10.1016/S0040-4039(01)83005-7

Reference yield: 89.0%

(3β,5α,6β)-6-methoxy-3,5-cyclocholestane-25-ol → 25-hydroxychlolesterol (2140-46-7)

Guidance literature:

With water; toluene-4-sulfonic acid; In 1,4-dioxane; at 80 ℃; for 6h;

upstream raw materials:

methyl magnesium iodide

27-nor-5-cholesten-3β-ol-25-one

3β-acetoxy-27-norcholest-5-en-25-one

methyl 3-acetoxy-23a-homo-5-cholen-24-oate

Downstream raw materials:

5-cholen-3β-ol

N^α-<4-(25-Hydroxy-5-cholesten-3β-yloxy)succinyl>-N-glycinamid

25-fuoro-5-cholesten-3β-ol

25-Hydroxy-1,4,6-cholestatrien-3-on

Refernces

• 1、 Zhao, Qian,Ji, Li,Qian, Guo-Ping,Liu, Jian-Gang,Wang, Zi-Qiang,Yu, Wan-Feng,Chen, Xin-Zhi. "Investigation on the synthesis of 25-hydroxycholesterol". . p. 1 - 5. Retrieved 2014.
• 2、 Ochi,Matsunaga,Shindo,Kaneko. "The convenient synthesis of 25-hydroxycholesterol". . p. 252 - 254. Retrieved 1979.
• 3、 Doiuchi, Daiki,Fujii, Yui,Hirai, Go,Igawa, Kazunobu,Makino, Kana,Takeda, Daiki,Tomooka, Katsuhiko,Uchida, Tatsuya,Yoritate, Makoto. "Preparation of oxysterols by c–h oxidation of dibromocholestane with ru(Bpga) catalyst". . . Retrieved 2022/01/04.
• 4、 -. "Methods for preparing cholesterol, and derivatives and analogs thereof". Paragraph 0344-0345; 0356-0357. . Retrieved 2021/04/07.