593-31-7

Usage

Uses

Used in Biochemistry and Pharmaceutical Applications:
SELACHYL ALCOHOL is used as a surfactant for forming micellar solutions and hexagonal liquid crystal phases in solution, which are essential for studying the properties and interactions of various biomolecules, including membrane proteins. Its ability to create these structures aids in understanding the behavior of biological systems and can contribute to the development of new drugs and therapies.
Used in Membrane Protein Research:
SELACHYL ALCOHOL is used as a host to grow membrane proteins, which are crucial components of cell membranes and play a significant role in various cellular processes. By providing an environment that supports the growth and stability of these proteins, SELACHYL ALCOHOL enables researchers to study their structure, function, and interactions with other molecules, ultimately contributing to the advancement of our understanding of cellular mechanisms and the development of targeted therapies.
Used in the Cosmetics Industry:
Glycerol 1-oleyl ether, a derivative of SELACHYL ALCOHOL, is used as a surfactant in the cosmetics industry. It forms micellar solutions and hexagonal liquid crystal phases in solution, which are beneficial for creating stable and effective formulations for various cosmetic products. These properties make it an ideal ingredient for moisturizers, cleansers, and other personal care products that require emulsification or solubilization of active ingredients.

InChI:InChI=1/C21H42O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24-20-21(23)19-22/h9-10,21-23H,2-8,11-20H2,1H3/b10-9+

Upstream product

• 22610-35-1 1-O-cis-9-octadecenyl isopropylideneglycerol 
• 143-28-2 oleoyl alcohol 
• 60501-41-9 oleyl-glycidyl ether 
• 35709-09-2 oleyl methanesulfonate 
• 6110-54-9 oleyl p-toluenesulfonate 
• 13044-38-7 (Z)-1-bromo-9-octadecene 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 

Downstream Products

• 82950-68-3 1-oleyl-3-trityl glycerol 
• 756531-64-3 rac-1-(Z-9-octadecenoyl)-2-(N-Boc-merphalanyl)-3-[3-(3-perylenoyl)propionyl]glycerol 
• 6076-41-1 2,3-bis[(Z)-octadec-9-enyloxy]propanol 
• 213738-46-6 Dimethyl 1-O-oleyl-2-O-methyl-rac-glycero-3-phosphate 
• 86299-21-0 1-O-oleyl-2-O-methyl-3-O-trityl glycerol 
• 76-84-6 triphenylmethyl alcohol 
• 6068-24-2 1-O-(Z)-9'-octadecenyl-3-O-trityl-sn-glycerol 

Relevant academic research and scientific papers

Synthesis of neutral ether lipid monoalkyl-diacylglycerol by lipid acyltransferases

In mammals, ether lipids exert a wide spectrum of signaling and structural functions, such as stimulation of immune responses, anti-tumor activities, and enhancement of sperm functions. Abnormal accumulation of monoalkyl-diacylglycerol (MADAG) was found in Wolman's disease, a human genetic disorder defined by a deficiency in lysosomal acid lipase. In the current study, we found that among the nine recombinant human lipid acyltrans-ferases examined, acyl-CoA:diacylglycerol acyltransferase (DGAT)1, DGAT2, acyl-CoA:monoacylglycerol acyltransferase (MGAT)2, MGAT3, acyl-CoA:wax-alcohol acyltransferase 2/MFAT, and DGAT candidate 3 were able to use 1-monoalkylglycerol (1-MAkG) as an acyl acceptor for the synthesis of monoalkyl-monoacylglycerol (MAMAG). These enzymes demonstrated different enzymatic turnover rates and relative efficiencies for the first and second acylation steps leading to the synthesis of MAMAG and MADAG, respectively. They also exhibited different degrees of substrate preference when presented with 1-monooleoylglycerol versus 1-MAkG. In CHO-K1 cells, treatment with DGAT1 selective inhibitor, XP-620, completely blocked the synthesis of MADAG, indicating that DGAT1 is the predominant enzyme responsible for the intracellular synthesis of MADAG in this model system. The levels of MADAG in the adrenal gland of DGAT1 KO mice were reduced as compared with those of the WT mice, suggesting that DGAT1 is a major enzyme for the synthesis of MADAG in this tissu. Our findings indicate that several of these lipid acyltransferases may be able to synthesize neutral ether lipids in mammals.

Synthesis of natural 1- O -alkylglycerols: A study on the chemoselective opening of the epoxide ring by onium quaternary salts (N and P) and ionic liquids

A chemoselective route for the synthesis of 1-O-alkylglycerols chimyl (1), batyl (2), and selachyl (3) is reported. These compounds can be naturally isolated from shark liver oil and the skin of animals such as stingrays and chimeras and exhibit potential anti-fouling activity. The synthetic approach developed in this work included two distinct methods of preparation. The first was based on solvent-free reactions catalyzed by onium quaternary salts (N and P) and ionic liquids; the second methodology was based on a series of one-pot reactions.

Sterol-modified phospholipids: Cholesterol and phospholipid chimeras with improved biomembrane properties

We synthesized a family of sterol-modified glycerophospholipids (SML) in which the sn-1 or sn-2 position is covalently attached to cholesterol and the alternative position contains an aliphatic chain. The SML were used to explore how anchoring cholesterol to a phospholipid affects cholesterol behavior in a bilayer. Notably, cholesterol in the SML retains the membrane condensing properties of free cholesterol regardless of the chemistry or position of its attachment to the glycerol moiety of the phospholipid. SMLs by themselves formed liposomes upon hydration and in mixtures between an SML and diacylglycerophospholipids (C14 to C18 chain length) the thermotropic phase transition is eliminated at the SML equivalent of about 30 mol % free cholesterol. Osmotic-induced contents leakage from SML (C14-C18) liposomes depends upon the linkage and position of cholesterol but in general is similar to that observed in 3/2 diacylphosphatidylcholine/cholesterol (mole ratio) liposomes. SML liposomes are exceptionally resistant to contents release in the presence of serum at 37°C. This is probably due to the fact that SML exchange between bilayers is more than 100 fold less than the exchange rate of free cholesterol in the same conditions. Importantly, SML liposomes containing doxorubicin are as effective in treating the murine C26 colon carcinoma as Doxil, a commercial liposome doxorubicin formulation. SMLs stabilize bilayers but do not exchange and hence provide a new tool for biophysical studies on membranes. They may improve liposomal drug delivery in organs predisposed to the extraction of free cholesterol from bilayers, such as the skin, lung, or blood.

Compositions containing lysophosphatidic acids which inhibit apoptosis and uses thereof

The invention provides anti-apoptotic compositions lysophosphatidic acids and methods for making and using the compositions. Such compositions can also contain LPA potentiating agents, including proteins, lipid membrane structures and polymers such as polyethylene glycols. The compositions can additionally contain other pharmaceutically effective agents such as drugs, antibiotics, wound healing agents and antioxidants.

COMPOSITION COMPRISING ETHER LIPID

The invention provides a composition suitable for administration to a mammalian, particularly human, subject wherein the composition comprises an active agent and an amphilic component (containing at least one amphiphile) wherein at least a portion of the amphiphilic component is an ether-linked lipid and wherein the composition includes a non-lamellar phase, preferably in the form of particles, or forms a non-lamellar phase on contact with an aqueous liquid. The aqueous liquid may be a body fluid. The invention also provides pharmaceutical and cosmetic formulations comprising the compositions and methods for their formation.

Lipase-catalysed kinetic resolution of 1-O-alkylglycerols by sequential transesterification

The natural S-configured chimyl, batyl and selachyl alcohols of the 1-O-alkylglycerol type were prepared by enantioselective lipase-catalysed transesterification. Their racemates were synthesised in two steps by reacting racemic solketal with the bromides of the corresponding fatty alcohols and a subsequent conversion of the intermediates into the 1-O-alkylglycerols by deprotection under acidic aqueous conditions. The Pseudomonas fluorescens lipase was employed to kinetically resolve the racemic 1-O-alkylglycerols by a sequential diacetylation process to afford them virtually enantiomerically pure. Dramatic enantioselectivity increase was observed for the saturated chimyl (E = 17-32) and batyl (E = 14-38) alcohols at decreased temperature, whereas for the monounsaturated selachyl (E = 12-13) alcohol no such temperature effects were observed.

Compositions containing lysophosphotidic acids which inhibit apoptosis and uses thereof

The present invention provides therapeutic compositions containing lysophosphotidic acids, methods for making the compositions, and methods of using the compositions in the preservation and treatment of organs.

Kinetic resolution of 1-O-alkylglycerols by lipase

Pseudomonas sp. lipase was employed to resolve kinetically 1-O- alkylglycerols by a sequential diacylation process. Only low or moderate E- values were obtained, but at approximately 60% conversion enantiomerically pure monoacetates were obtained of the natural S-configuration for glyceryl ether lipids.

Synthesis of 1-O-alkyl-2-O-methyl-glycerophospholipids with potential antitumor activity

Some synthetic alkyl-lysophospholipid analogs have been described as a new class of immunopotentiating and antitumor agents. Among them, 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine has been reported to possess the highest antitumor activity. A new method for the synthesis of this compound and of the ethanolamine- and serine-containing analog is reported. 1-Alkyl-2-methyl-rac-glycerol, prepared from 1,2-isopropylidene-glycerol, is phosphorylated and the intermediate is condensed either with N-t-BOC-protected ethanolamine or with N-t-BOC-protected serine benzhydryl ester. The choline-derivative is obtained by methylation with CH3I of the ethanolamine derivative. The same synthetic sequence has been used also for synthesizing compounds unsaturated at the fatty alkyl chain in position 1 of the glycerol moiety. Preliminary observation are reported on the selective cytolytic action of the compounds on a tumor cell line.