22R-Hydroxycholesterol
Basic information
- CAS
17954-98-2- Standard SMILES
CC(C)CC[C@@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
RZPAXNJLEKLXNO-GFKLAVDKSA-N- Molecular formula
- C27H46O2
- Average molar mass
- 402.7 g/mol
- Monoisotopic mass
- 402.34978071
Overview
(22R)-22-hydroxycholesterol is an oxysterol that is the 22R-hydroxy derivative of cholesterol. It is a 3beta-hydroxy-Delta(5)-steroid, a 22-hydroxy steroid and an oxysterol. It is functionally related to a cholesterol.
Names & identifiers
- Preferred name
- 22R-Hydroxycholesterol
- IUPAC
- (3S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R)-3-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
- 22(R)-hydroxy Cholesterol
- Molecular formula
- C27H46O2
- Molecular weight
- 402.65
Names & synonyms
22(R)-Hydroxycholesterol22R-hydroxycholesterol(22R)-22-Hydroxycholesterolcholest-5-en-3beta,22R-diol(3beta,22R)-Cholest-5-ene-3,22-diol(3S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R)-3-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-olCHEBI:67237(3S,8S,9S,10R,13S,14S,17R)-17-((2S,3R)-3-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-olRefChem:91032717954-98-222beta-Hydroxycholesterol(22R)-Hydroxycholesterol
Show more names
22(R)-OH-CH22α-hydroxycholesterol22BF-HYDROXYCHOLESTEROLCholesterol 22α-Hydroxy22α-Hydroxy Cholesterol22(R)-HydroxycholesteroChlorambucil Impurity 8
22R-OHC22-alpha-Hydroxy Cholesterol22a-Hydroxy CholesterolCholest-5-ene-3,22-diol, (3beta,22R)-22alpha-Hydroxy Cholesterol(22R)-cholest-5-ene-3beta,22-diolNarthesterolCHEMBL422904
Properties
Computed structural properties
- XLogP
- 7
- 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
- 624
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Physical DescriptionSolid
Collision Cross Section217.74 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 171 · 171-174°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
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 15.01 · 15.01±0.20(Predicted)
- color
- White to Off-White
- InChIKey
- RZPAXNJLEKLXNO-QUOSNDFLSA-N
- SMILES
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Tissue LocationsAdrenal Cortex
Cellular LocationsExtracellular
Metabolite Pathways11-beta-hydroxylase deficiency (CYP11B1)
Applications
DescriptionThe liver X receptors (LXRα and LXRβ) are nuclear hormone receptors whose native ligands are oxysterols. LXRs regulate the oxysterol-induced expression of cholesterol 7α-hydroxylase, the rate limiting enzyme of classic bile acid synthesis. 22(R)-hydroxy Cholesterol is an endogenous agonist for LXRs that activates LXRα with an EC50 value of 325 nM. 22(R)-hydroxy Cholesterol, acting through LXR heterodimerized with the retinoid X receptor, induces the expression of the ABCA1 reverse cholesterol transporter. This activity increases the efflux of cholesterol from enterocytes and thus inhibits the overall absorption of cholesterol. 22(R)-hydroxy Cholesterol can be used as a substrate to monitor cholesterol transport or as an endogenous positive control for testing LXR agonists which have potential as therapeutic agents for the treatment of atherosclerosis.
UsesThe 22R-metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.
UsesBovine aortic endothelial cells were treated with 22(R)-Hydroxycholesterol to study the effects on production of free radicals and in studies related to fatty acid metabolism.
General Description22(R)-hydroxycholesterol is a diastereomer of 22(S)-hydroxycholesterol. It is present in neonate brain.
Additional notes
DefinitionChEBI: An oxysterol that is the 22R-hydroxy derivative of cholesterol.
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