2126-93-4

Basic information

• Product Name: cholesterylamine
• Synonyms: cholesterylamine;3-beta-aminocholesterol
• CAS NO: 2126-93-4
• Molecular Formula: C₂₇H₄₇N
• Molecular Weight: 385.67
• Mol File: 2126-93-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 98 °C(Solv: methanol (67-56-1))
• Boiling Point: 470.8°Cat760mmHg
• Flash Point: 234.5°C
• Appearance: /
• Density: 0.96g/cm³
• Vapor Pressure: 4.93E-09mmHg at 25°C
• Refractive Index: 1.526
• PKA: 10?+-.0.70(Predicted)
• CAS DataBase Reference: cholesterylamine(CAS DataBase Reference)
• NIST Chemistry Reference: cholesterylamine(2126-93-4)
• EPA Substance Registry System: cholesterylamine(2126-93-4)

Safety Data

• Hazardous Substances Data: 2126-93-4(Hazardous Substances Data)

Usage

Description

Cholesterylamine, also known as (3β)-Cholest-5-en-3-amine, is a derivative of cholesterol with an amine group attached to the steroid nucleus. It is known for its ability to enhance the magnetic susceptibility of certain structures and has potential antiviral properties.

Uses

Used in Magnetic Resonance Applications:
Cholesterylamine is used as an enhancer for the magnetic susceptibility of lanthanide-chelating bicelles in bilayer structures. This application is particularly useful in the field of magnetic resonance imaging (MRI) and spectroscopy, where it can improve the quality of images and data obtained from these techniques.
Used in Antiviral Applications:
In the pharmaceutical industry, cholesterylamine is used as a potential antiviral agent. It shows a new mode of antiviral action by directly targeting the virus envelope and its biological functions, which could be beneficial in the development of new treatments for viral infections.
Used in Drug Delivery Systems:
Similar to gallotannin, cholesterylamine could also be employed in the development of novel drug delivery systems. Its unique properties might allow for improved targeting and delivery of therapeutic agents, potentially enhancing their efficacy and reducing side effects.

InChI:InChI=1/C27H47N/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17,28H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 38759-57-8 cholest-5-en-3β-yl-isopropyliden-amine 
• 14412-92-1 N-acetyl-cholest-5-en-3β-amine 
• 1182-65-6 3β-Tosyloxy-Δ⁵-cholesten 
• 530-62-1 1,1'-carbonyldiimidazole 
• 123147-62-6 3β-methanesulfonyl-5-cholestene 
• 96290-22-1 (3S,8S,9S,10R,13R,14S,17R)-3-azido-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene 
• 907574-94-1 cholest-5-ene-3β-carboxylic acid hydrazide 
• 601-54-7 Cholest-5-en-3-one 
• 474-77-1 epicholesterol 
• 7144-08-3 Cholesteryl chloroformate 
• 390762-93-3 N-cholesteryl-2-nitrobenzenesulfonamide 
• 57-88-5 cholesterol 

Downstream Products

• 38759-54-5 3β-(4'-Chlorbutyramido)-5-cholesten 
• 440358-97-4 N-[3-(tert-butoxycarbonylamino)propyl]-N-cholesteryl-2-nitrobenzenesulfonamide 
• 828293-17-0 tert-butyl 3-[(3-{(3β)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)amino]-3-oxopropylcarbamate 
• 879288-20-7 3-amino-N-(2-{3-[[17-(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-yl]-(2-nitro-benzenesulfonyl)-amino]-propylcarbamoyl}-ethyl)-propionamide 
• 828293-20-5 tert-butyl 3-({3-[(3-{(3β)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)amino]-3-oxopropyl}amino)-3-oxopropylcarbamate 
• 828293-31-8 N-(3-{(3β)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)-6-[(2,4-dinitrophenyl)amino]hexanamide 
• 828293-46-5 N-(3-{(3β)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)-6-(7-nitrobenzofurazan-4-ylamino)hexanamide 
• 828293-27-2 N-{3-[(3-{(3β)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)amino]-3-oxopropyl}-6-[(2,4-dinitrophenyl)amino]hexanamide 
• 828293-42-1 N-{3-[(3-{(3β)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)amino]-3-oxopropyl}-6-(7-nitrobenzofurazan-4-ylamino)hexanamide 
• 828293-23-8 N-[3-({3-[(3-{(3β)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)amino]-3-oxopropyl}amino)-3-oxopropyl]-6-[(2,4-dinitrophenyl)amino]hexanamide 
• 828293-37-4 N-[3-({3-[(3-{(3β)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)amino]-3-oxopropyl}amino)-3-oxopropyl]-6-(7-nitrobenzofurazan-4-ylamino)hexanamide 
• 55750-48-6 N-methoxycarbonylmaleimide 

Relevant articles and documents

Sterilizing Immunity against SARS-CoV-2 Infection in Mice by a Single-Shot and Lipid Amphiphile Imidazoquinoline TLR7/8 Agonist-Adjuvanted Recombinant Spike Protein Vaccine**

The search for vaccines that protect from severe morbidity and mortality because of infection with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), the virus that causes coronavirus disease 2019 (COVID-19) is a race against the clock and the virus. Here we describe an amphiphilic imidazoquinoline (IMDQ-PEG-CHOL) TLR7/8 adjuvant, consisting of an imidazoquinoline conjugated to the chain end of a cholesterol-poly(ethylene glycol) macromolecular amphiphile. It is water-soluble and exhibits massive translocation to lymph nodes upon local administration through binding to albumin, affording localized innate immune activation and reduction in systemic inflammation. The adjuvanticity of IMDQ-PEG-CHOL was validated in a licensed vaccine setting (quadrivalent influenza vaccine) and an experimental trimeric recombinant SARS-CoV-2 spike protein vaccine, showing robust IgG2a and IgG1 antibody titers in mice that could neutralize viral infection in vitro and in vivo in a mouse model.

MODIFIED PIGMENT EPITHELIUM-DERIVED FACTOR (PEDF) PEPTIDES AND USES THEREOF FOR TREATING NEOVASCULAR DISEASES, INFLAMMATORY DISEASES, CANCER, AND FOR CYTOPROTECTION

Disclosed are modified pigment epithelium-derived factor (PEDF) peptides, particulate carrier prodrugs thereof, and pharmaceutical compositions comprising the peptides or particulate carrier prodrugs. The peptides, particulate carrier prodrugs, and pharmaceutical compositions may be used to treat diseases and disorders that are amenable to treatment with anti-angiogenic agents, anti-tumorigenic agents, anti-fibrotic agents, chemotherapy-protecting agents, and immune stimulating agents

Evaluation of steroidal amines as lipid raft modulators and potential anti-influenza agents

The influenza A virus (IFV) possesses a highly ordered cholesterol-rich lipid envelope. A specific composition and structure of this membrane raft envelope are essential for viral entry into cells and virus budding. Several steroidal amines were investigated for antiviral activity against IFV. Both, a positively charged amino function and the highly hydrophobic (C log P ≥ 5.9) ring system are required for IC50 values in the low μM range. An amino substituent is preferential to an azacyclic A-ring. We showed that these compounds either disrupt or augment membrane rafts and in some cases inactivate the free virus. Some of the compounds also interfere with virus budding. The antiviral selectivity improved in the series 3-amino, 3-aminomethyl, 3-aminoethyl, or by introducing an OH function in the A-ring. Steroidal amines show a new mode of antiviral action in directly targeting the virus envelope and its biological functions.