39840-30-7

Usage

Uses

Used in Personal Care and Cosmetic Industry:
2-(dimethylamino)ethyl stearate is used as an emulsifier for its ability to stabilize and blend ingredients in formulations, ensuring a uniform texture and improving the product's performance on the skin or hair.
2-(dimethylamino)ethyl stearate is used as a conditioner to provide softness, manageability, and a smooth feel to the skin or hair, enhancing the overall user experience.
Used in Skincare Products:
2-(dimethylamino)ethyl stearate is used as a thickening agent to improve the consistency and stability of skincare products, making them easier to apply and more effective.
2-(dimethylamino)ethyl stearate is used as a surfactant to help cleanse the skin by removing dirt and impurities, contributing to a clean and refreshed complexion.
Used in Haircare Products:
2-(dimethylamino)ethyl stearate is used as a texturizing agent to improve the manageability and appearance of hair, making it easier to style and maintain.
2-(dimethylamino)ethyl stearate is used as a cleansing agent in haircare products to help remove buildup and impurities, promoting a clean and healthy scalp environment.

InChI:InChI=1/C22H45NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23(2)3/h4-21H2,1-3H3

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 112-76-5 Stearoyl chloride 
• 57-10-3 1-hexadecylcarboxylic acid 
• 57-11-4 stearic acid 

Downstream Products

• 24902-45-2 O-stearoylcholine Iodide 
• 25234-57-5 O-stearoylcholine chloride 
• 2932-74-3 trimethyl-(2-palmitoyloxy-ethyl)-ammonium; chloride 

Relevant academic research and scientific papers

Thermal behavior of long-chain alkanoylcholine soaps

Long-chain alkanoylcholines prepared from fatty acids (nACh) are fully sustainable cationic surfactants that are known for their biological and medicinal properties. In the present work the thermal behavior of the homologous series of alkanoylcholine iodides with n = 12, 14, 16 and 18, has been examined within the 25-200 °C range of temperatures. Up to three thermotropic phases have been identified, and the thermal transitions implied in their interconversion have been characterized by DSC and simultaneous WAXS and SAXS analysis carried out in real-time. All three phases consist of a bilayered structure with alkanoyl chains confined in the space between the head group layers and interdigitated to a greater or lesser extent. Melting-crystallization of either the polymethylene segments or the choline iodide groups is involved in such transitions. Additionally, a crystal phase consisting also of a bilayered structure but excluding side chain interdigitation was observed upon crystallization from solution and its structure was elucidated by single-crystal X-ray diffraction direct methods. The close correlation existing between thermal properties, phase structure and n has been brought into evidence.

Effect of hofmeister series anions on the thermotropic phase behavior of bioactive O -acylcholines

O-Acylcholines (OACs), which are true cationic lipids due to the quaternary ammonium functionality in the headgroup, exhibit interesting biological activities and medicinal properties. In the present study, a homologous series of OACs with even chain lengths (n = 12-20) have been synthesized, and their thermotropic and chaotropic phase transitions have been characterized. The role of various anions (Cl-, Br-, I-, NO 3-, SO42-, ClO3 -, ClO4-) on the phase behavior of O-stearoylcholine was investigated by calorimetric, spectroscopic, and turbidimetric approaches. The results obtained revealed that in aqueous dispersion O-stearoylcholine undergoes a cooperative phase transition from a gel phase to a micellar structure and that the transition temperature increases when the counterions are changed in the Hofmeister series. Single-crystal X-ray diffraction studies showed that O-stearoylcholine iodide forms an interdigitated bilayer structure, with the polymethylene chain adopting an all-trans conformation. The Hofmeister effect and phase behavior were explained using the concepts of matching water affinities, water penetration into the bilayer, and electrostatic repulsion. It was also observed that one counterion per molecule is sufficient to strongly modulate the phase properties of the lipid/surfactant.

Improved LC-MS method for the determination of fatty acids in red blood cells by LC-orbitrap MS

We report a new method for fast and sensitive analyses of biologically relevant fatty acids (FAs) in red blood cells (RBC) by liquid chromatography mass spectrometry (LC-MS). A new chemical derivatization approach was developed forming picolylamides from FAs in a quantitative reaction. Fourteen derivatized FA standards, including saturated and unsaturated FAs from C14 to C22, were efficiently separated within 15 min. In addition, the use of a recently introduced benchtop orbitrap mass spectrometer under positive electrospray ionization (ESI) full scan mode showed a 2-10-fold improvement in sensitivity compared with a conventional tandem MS method, with a limit of detection in the low femtomole range for saturated and unsaturated FAs. The developed method was applied to determine FA concentrations in RBC with intra- and interday coefficients of variation below 10%.

Dimer poly-quaternary ester compounds

The present invention relates to a novel class of polymeric compounds having specific quaternized amine based upon a dimer acid reacted with an alkanolamine to make an ester quaternary compound. Dimer acid is a C-36 diacid having a cyclic structure and two amine groups that allow for the synthesis of a high molecular weight cationic compound which is extremely substantitive to human skin and are well tolerated by human tissue making them suitable for use preparation of barrier products for personal care applications. These materials are dimethylaminopropyl amine free, which is highly desirable in personal care applications.

Dimer poly-quaternary ester compounds

The present invention relates to a novel class of polymeric compounds having specific quaternized amine based upon a dimer acid reacted with an alkanolamine to make an ester quaternary compound. Dimer acid is a C-36 diacid having a cyclic structure and two amine groups that allow for the synthesis of a high molecular weight cationic compound which is extremely substantitive to human skin and are well tolerated by human tissue making them suitable for use preparation of barrier products for personal care applications. These materials are dimethylaminopropyl amine free, which is highly desirable in personal care applications.

Softener composition

A softener composition that can impart a high softening effect to clothes irrespective of the state of rinsing water, which contains (a) a compound of formula (1) below, (b) a compound of formula (3) below, and (c) a specific anionic surfactant, wherein the mole ratios between the components (a), (b) and (c) satisfy the following relationship: [(a)+(b)]/(c)=9/1 to 4/6; and wherein R1 represents a C13-36 alkyl group or the like, R10 and R12 respectively represent a C8-36 alkyl group or the like, R2, R11 and R13 respectively represent a C1-6 alkylene group, R3, R4, and R14 respectively represent a C1-3 alkyl group or the like, A, D and E respectively represent —COO—, —CONH— or the like, and “a”, “c” and “d” respectively denote 0 or 1.

Cationic amphiphiles with G-protein-stimulatory activity: Studies on the role of the basic domain in the activation process

2-Substituted histamines, which are cationic-amphiphilic, activate pertussis toxin-sensitive G-proteins by a receptor-independent mechanism. Lipophilicity is an important determinant for this G-protein activation, but the influence of basicity remained unclear. We prepared four imidazole-containing compounds and nine alkylamines with different basicity and studied their effects on high-affinity GTP hydrolysis in HL-60 membranes. The substances contained a lipophilic domain (L) and polar (P) and/or cationic (C) domains. Compared to 2-substituted histamines (L-P-C), the corresponding L-C-P type compounds were less potent and effective which, however, were still more active than L-P-P type substances. Among alkylamines, 2-octadecylaminoethyl-N,N-diethylamine (11) was the most potent GTPase activator (pEC50 = 5.7; 100% stimulation above basal). Conversely, 3-(5-hydroxyundecylamino)propylamine (15) was the most efficient compound (pEC50 = 4.3; 160% stimulation above basal). Compared to compounds 11 and 15, which belong to the L-C-C type, the corresponding L-P-C type compounds were less active. Thus, among 2-substituted histamines and alkylamines, a terminal cationic domain is critical for potent and/or effective receptor-independent G-protein activation. An L-C-X structure (X = P or C) is more favorable for G-protein activation than a L-P-X structure. Potency and efficiency of receptor-independent G-protein activators are independently determined drug parameters.

2-(Dimethylamino)ethyl Esters of Fatty Acids: A Previously Unknown Class of Natural Products

The F-acid 1 was incubated with bovine liver homogenisate in the presence of S-adenosylmethione (SAM).One of the reaction products of the incubation was identified as its 2-(dimethylamino)ethyl ester 3.The knowledge of the chemical, chromatographical, and mass spectrometrical behaviour of 3 allowed the identification of 2-(dimethylamino)ethyl esters of fatty acids 5, 7-9 in bovine liver, a previously unknown class of natural products.