68400-57-7

Basic information

• Product Name: N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]stearamide
• Synonyms: N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]stearamide;N-[2-Hydroxy-1,1-bis(hydroxymethyl)ethyl]octadecanamide
• CAS NO: 68400-57-7
• Molecular Formula: C₂₂H₄₅NO₄
• Molecular Weight: 387.597
• EINECS: 270-047-1
• Mol File: 68400-57-7.mol

Chemical Properties

• Boiling Point: 593.3°Cat760mmHg
• Flash Point: 312.6°C
• Appearance: /
• Density: 0.993g/cm³
• Vapor Pressure: 1.5E-16mmHg at 25°C
• Refractive Index: 1.486
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Very Slightly), DMSO (Very Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]stearamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]stearamide(68400-57-7)
• EPA Substance Registry System: N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]stearamide(68400-57-7)

Safety Data

• Hazardous Substances Data: 68400-57-7(Hazardous Substances Data)

Usage

Uses

Used in Gene Delivery Systems:
N-[2-Hydroxy-1,1-bis(hydroxymethyl)ethyl]stearamide is used as a reactant in the development of gene delivery systems. Its application is particularly focused on the creation of tripodal cationic lipids that possess programmed biodegradability. This feature is crucial in ensuring the safe and effective delivery of genetic material, making it a valuable component in the field of genetic research and therapy.
Used in Cosmetics Industry:
In the cosmetics industry, N-[2-Hydroxy-1,1-bis(hydroxymethyl)ethyl]stearamide is used as an emollient, providing a smooth and soft texture to the skin. Its ability to form stable structures makes it an ideal ingredient for various cosmetic products, enhancing their performance and efficacy.
Used in Pharmaceutical Industry:
N-[2-Hydroxy-1,1-bis(hydroxymethyl)ethyl]stearamide also finds application in the pharmaceutical industry, where it is utilized in the formulation of drugs. Its unique properties allow for the creation of more effective and stable drug compounds, contributing to the development of innovative treatments and therapies.

InChI:InChI=1/C22H45NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(27)23-22(18-24,19-25)20-26/h24-26H,2-20H2,1H3,(H,23,27)

Upstream product

• 57-11-4 stearic acid 
• 77-86-1 2-amino-2-hydroxymethyl-1,3-propanediol 
• 1146965-63-0 N-[tris(tert-butyldimethylsilyloxymethyl)methyl]octadecamide 
• 1185-53-1 tris hydrochloride 
• 112-76-5 Stearoyl chloride 

Relevant articles and documents

Synthesis, supramolecular organization and thermotropic phase behaviour of N-acyltris(hydroxymethyl)aminomethane

Herein, we reported the supramolecular organization of N-acyltris(hydroxymethyl)aminomethane (NATM) in the solid state as well as in aqueous solution. Single crystal X-ray diffraction revealed that NATM adopts a fully interdigitized structure. The thermodynamic parameters associated with thermotropic phase behaviour of NATM was determined by differential scanning calorimetry. The molecular packing and phase state of the NATM analyzed by laurdan and prodan fluorescence supports the formation of an interdigitized phase in aqueous solution. The potential application of the self-assembled NATM vesicles was demonstrated through entrapping model drug, Rhodamine B.

Safe and efficient in vitro and in vivo gene delivery: Tripodal cationic lipids with programmed biodegradability

The therapeutic use of nucleic acids has long been heralded as a panacea of medicinal opportunity, a vision enhanced by the introduction of RNA interference technology. The Achilles heel of such an approach is the in vivo delivery of the desired nucleic acid into cells, a practice that lacks selectivity, safety and/or efficiency. Herein we report the safe and efficacious in vitro and in vivo delivery of nucleic acids using tripodal biodegradable cationic lipids. Toxicity reduction and transfection potency of these novel amphiphiles were addressed by designing the compounds to undergo complete intracellular degradation thereby enhancing cargo release while minimising toxicity and potential tissue accumulation. Compounds demonstrated high-efficiency in transfecting DNA into cells both in vitro and in vivo with no signs of toxicity, thus potentially offering a safer alternative to viral transfection for gene therapy application. The Royal Society of Chemistry.

NOVEL SYNTHETIC ANALOGS OF SPHINGOLIPIDS

The present invention provides new ceramide analogs indicated as the compounds of formula (II). These novel analogs exhibit a significant anti cancerous effect and are therefore provided as a pharmaceutical composition for treating cell proliferative diseases, neurodegenerative disorders, metabolism-associated conditions, infectious diseases, and immune-related disorders. The invention further provides combined compositions and kits combining the novel ceramide analogs of formula (II) with an additional therapeutic agent.

CATIONIC LIPIDS

This invention relates to cationic lipids. More particularly the invention relates to biodegradable cationic lipids having a plurality of cationic headgroups and one or more lipophilic tail groups. The lipids are of utility in various applications, and in particular in permitting transfection of molecules, and in particular DNA and RNA, into cells. As such the lipids have specific utility in the field of gene therapy as well as other applications such as delivery of small molecules into cells, detergents, and metal ion complexation for medical or industrial applications.

The effect of molecular shape and microphase segregation on the formation of liquid crystal phases in poly-ols

In this article we examine the effect of molecular shape on the formation of thermotropic phases of alkyl-substituted poly-ols. The relationship between the cross-sectional area of the hydrophilic head group with respect to the that of the hydrophilic tails determines the type of mesophase formed. The results obtained are similar to those found for the formation of lyotropic phases.