Basic information
- CAS
2140-46-7- Standard SMILES
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
INBGSXNNRGWLJU-ZHHJOTBYSA-N- Molecular formula
- C27H46O2
- Average molar mass
- 402.7 g/mol
- Monoisotopic mass
- 402.34978071
Overview
25-hydroxycholesterol is a 25-hydroxy steroid and an oxysterol. It has a role as a human metabolite. It is functionally related to a cholesterol.
Names & identifiers
- Preferred name
- 25-Hydroxycholesterol
- IUPAC
- (3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- English name
- 25-Hydroxycholesterol
- Molecular formula
- C27H46O2
- Molecular weight
- 402.65
Names & synonyms
Show more names
Database identifiers
- CAS
2140-46-7- PubChem CID
- 65094
- DTXSID
DTXSID5044023- ChEMBL
CHEMBL169046- ChEBI
CHEBI:42977- UNII
- 767JTD2N31
- EC Number
- 635-752-4
- Nikkaji
- J80.397I
Properties
Computed structural properties
- XLogP
- 6.8
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 5
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 636
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 177 · 177-179 °C
- Boiling point
- 513.1 · 513.1±23.0 °C(Predicted)
- Density
- 1.03 · 1.03±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 50 mg/mL, · chloroform: 50 mg/mL, clear, colorless to slightly yellow
- pka
- 15.03 · 15.03±0.70(Predicted)
- form
- solid
- color
- White or pale yellow
- biological source
- synthetic (organic)
- Merck
- 13 · 13,4846
- BRN
- 3161259 · 3161259
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
- InChIKey
- INBGSXNNRGWLJU-ZHHJOTBYSA-N
- SMILES
- [C@@]12([H])CC[C@H]([C@H](C)CCCC(O)(C)C)[C@@]1(C)CC[C@]1([H])[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21[H] |&1:0,4,5,14,18,20,24,30,r|
- FDA UNII
- 767 JTD2N31 · 767JTD2N31
- UNSPSC Code
- 41141804 · 41141804
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 302 · H302-H312-H315-H319-H332-H335-H373
- Precautionary statements
- 261 · P261-P280-P305+P351+P338
- Hazard Codes
- Xn
- Risk Statements
- 20 · 20/21/22-36/37/38-48
- Safety Statements
- 26 · 26-36-45
- WGK Germany
- 3 · 3
- HS Code
- 29062990 · 29062990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- wgk
- 3
- hs_code
- 29062990
- risk_code
- 20/21/22-36/37/38-48
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 26-36-45
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H312-H315-H319-H332-H335-H373
- Precautionary statements
- P261-P280-P305+P351+P338
Chemistry & industry
Applications
Description25-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.
Uses25-Hydroxycholesterol was used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.
UsesAn 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.
General Description25-hydroxy-cholesterol is a side chain substituted oxysterol. Avanti′s unique sterol reverses cataracts in mice. Gestwicki′s team ...... settled on compound 29, a steroid found naturally in the bloodstream but not in the lens, which has no blood supply. Mice with age-related and hereditary cataracts received drops in the right eye, whereas the left eye went untreated. After just a few weeks, the treated eye was visibly clearer, says Gestwicki, who conducted the work while at the University of Michigan. Cataract severity is measured on a scale of zero to four, with four being the worst case. On average, mice in the study had about a one-grade improvement in cataract severity after 4 weeks of treatment. Science DOI: 10.1126/science.aad7400 It has been recently shown that activation of a macrophage toll-like receptor (TLR) by microbial antigens induces synthesis of 25-hydroxycholesterol, and that this oxysterol potently suppresses IgA production.
Suppliers100 total
Additional notes
DefinitionChEBI: 25-hydroxycholesterol is an oxysterol and a 25-hydroxy steroid. It has a role as a human metabolite. It is functionally related to a cholesterol.
Related reactions
Compound notes
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