6145-69-3

Usage

Uses

1. Used in Pharmaceutical Industry:
1-O-Hexadecyl-rac-glycerol is used as a key component in the synthesis of N-linked and diglycosylated glucosamine-based glycerolipids. These glycerolipids serve as antitumor agents, targeting and combating cancer cells effectively.
2. Used in Chemical Synthesis:
1-O-Hexadecyl-rac-glycerol is utilized as an intermediate in the synthesis of various complex molecules, particularly those with potential applications in the pharmaceutical and chemical industries. Its unique structure allows for the creation of novel compounds with specific properties and functions.

InChI:InChI=1/C19H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-22-18-19(21)17-20/h19-21H,2-18H2,1H3

Upstream product

• 26459-58-5 allyl-1-hexadecyl ether 
• 20779-14-0 methanesulfonic acid hexadecyl ester 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 6068-28-6 tosylate de n-hexadecyle 
• 89496-73-1 4-(n-hexadecyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 36653-82-4 1-Hexadecanol 
• 4860-03-1 1-Chlorohexadecan 
• 7647-01-0 hydrogenchloride 
• 91326-86-2 16-<(2S)-(2,3-(isopropylidenedioxy)propyl)oxy>hexadecane 
• 112-82-3 hexadecanyl bromide 
• 82002-20-8 1-O-hexadecyl-3-O-trityl-rac-glycerol 
• 18371-73-8 1-chloro-3-hexadecylhydroxy-2-propanol 
• 556-52-5 oxiranyl-methanol 
• 117606-92-5 cetyl glycidyl ether 

Downstream Products

• 119039-42-8 Ditritylchimylalkohol 
• 21994-82-1 1-O-hexadecyl-2,3-diacetylglycerol 
• 82002-20-8 1-O-hexadecyl-3-O-trityl-rac-glycerol 
• 133281-05-7 5-Hexadecyloxymethyl-2-benzyloxymethyl-1,3-dioxolane 
• 72487-76-4 (3-Hexadecyloxy-2-hydroxypropyl) p-toluenesulfonate 
• 118469-68-4 1-(hexadecyloxy)-3-((4-methoxyphenyl)diphenylmethoxy)-2-propanol 
• 17752-41-9 1-hexadecyl-2-palmitoylglycerol 
• 544-77-4 1-iodohexadecane 
• 56-81-5 glycerol 
• 946568-34-9 [1-(4,4'-dimethoxytrityl)]-3-hexadecylglycerol 
• 4239-20-7 C₂₁H₄₄O₇S₂ 
• 506-03-6 chimyl alcohol 
• 74389-68-7 PAF 
• 78119-19-4 2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate 

Relevant academic research and scientific papers

Long-lived and highly conducting ion channels formed by lipophilic ethylenediamine palladium(ii) complexes

The synthesis of a lipophilic ethylenediamine palladium(ii) complex and its activity in planar bilayer membranes are reported. In acetonitrile solution containing one equivalent of 4,4-bipyridine the complex forms the expected metallosupramolecular tetrameric square. The same mixture provokes transmembrane conductance of three types: an initial period of erratic behavior, occasional short channel-like openings, and frequent very long-lived and highly conducting channel openings. The apparent pore radii of both short and long openings vary continuously over the range of 0.1-1.5 nm, and long-lived pores will form in the absence of 4,4′-bipyridine. The long-lived channels are presumed to involve an extended aggregate of the palladium complex and lipids surrounding a toroidal pore in the membrane. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

NUCLEIC ACID OF FORMULA (I): GlXmGn, OR (II): ClXmCn, IN PARTICULAR AS AN IMMUNE-STIMULATING AGENT/ADJUVANT

The present invention relates to a nucleic acid of the general formula (I): GlXmGn, or (II): ClXmCn, which may be modified by a lipid. The nucleic acid of the invention acts as an immune-stimulating agent inducing the innate immune response. The invention relates further to a pharmaceutical composition (in a first embodiment), each containing an immune-stimulating agent according to the invention in combination with a pharmaceutically active carrier/vehicle (and, optionally, further auxiliary substances, additives and/or further adjuvants). In another embodiment, the inventive nucleic acid is combined with at least one pharmaceutically active component, a pharmaceutically acceptable carrier/vehicle (and, optionally, further auxiliary substances, additives and/or further adjuvants). Accordingly, the present invention is directed to a vaccine, which corresponds to a pharmaceutical composition of the invention (second embodiment), wherein the pharmaceutically active component induces a specific immune response (e.g. an antigen). The present invention relates likewise to the use of a nucleic acid of the invention or a pharmaceutical composition according to the invention for the treatment of infectious diseases, autoimmune diseases, allergies or cancer diseases.

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.

Design, synthesis and cytotoxicity of chimeric erlotinib-alkylphospholipid hybrids

Two series of erlotinib-alkylphospholipid hybrids were prepared and evaluated for their antiproliferative activities against a panel of four cell lines representing lung, breast, liver and skin cancers using erlotinib and miltefosine as reference standards. Amide analogs elicited more enhanced cytotoxic activity than analogous esters. Amide derivatives 8d and 8e exhibited promising broad-spectrum antiproliferative activity and higher efficacy than reference erlotinib and miltefosine. Their cellular GI50 values was in the ranges of 24.7–46.9 μM and 26.8–43.1 μM for 8e and 8d respectively. Assay results of the inhibitory activity of the prepared compounds on EGFR kinase reaction and Akt phosphorylation in conjugation with statistical correlation analysis indicated that other mechanisms might contribute to their elicited cytotoxicities. In addition, statistical correlation analysis revealed that mechanisms of elicited cytotoxicities for amide series might be different from ester series. In addition, correlation analysis indicated variations in the mechanisms according to the types of cell line.

Synthesis of alkyl-glycerolipids standards for gas chromatography analysis: Application for chimera and shark liver oils

Natural O-alkyl-glycerolipids, also known as alkyl-ether-lipids (AEL), feature a long fatty alkyl chain linked to the glycerol unit by an ether bond. AEL are ubiquitously found in different tissues but, are abundant in shark liver oil, breast milk, red blood cells, blood plasma, and bone marrow. Only a few AEL are commercially available, while many others with saturated or mono-unsaturated alkyl chains of variable length are not available. These compounds are, however, necessary as standards for analytical methods. Here, we investigated different reported procedures and we adapted some of them to prepare a series of 1-O-alkyl-glycerols featuring mainly saturated alkyl chains of various lengths (14:0, 16:0, 17:0, 19:0, 20:0, 22:0) and two monounsaturated chains (16:1, 18:1). All of these standards were fully characterized by NMR and GC-MS. Finally, we used these standards to identify the AEL subtypes in shark and chimera liver oils. The distribution of the identified AEL were: 14:0 (20–24%), 16:0 (42–54%) and 18:1 (6–16%) and, to a lesser extent, (0.2–2%) for each of the following: 16:1, 17:0, 18:0, and 20:0. These standards open the possibilities to identify AEL subtypes in tumours and compare their composition to those of non-tumour tissues.

PROCESS FOR PREPARING A POLYOL ETHER

The present invention relates to a process for preparing a polyol ether of formula (I), comprising a step of reductive alkylation involving a compound of general formula (II) and a compound of general formula (III): in which R1, R2, R3 and R4 are as defined in claim 1.

Selective synthesis of 1-O-Alkyl(poly)glycerol ethers by catalytic reductive alkylation of carboxylic acids with a recyclable catalytic system

(Poly)glycerol monoethers were synthesized in good yield and selectivity by the catalytic reductive alkylation of glycerol, diglycerol, and triglycerol with readily available, cheap and/or bio-sourced carboxylic acids. The reaction was catalyzed by 1 mol % of Pd/C under 50 bar H2 using an acid ion-exchange resin as a recyclable cocatalyst. The catalytic system was recycled several times, and a mechanism is proposed for this transformation.

OXIDIZED THIOPHOSPHOLIPID COMPOUNDS AND USES THEREOF

Novel oxidized thiophospholipids are provided herein, as well as methods for producing same, and uses thereof in treating or preventing an inflammation associated with endogenous oxidized lipids and related conditions. Exemplary oxidized thiophospholipid according to embodiments described herein have the formula: (I) wherein X1, X2, A1, A2, B', B'', D' and D'' are as described herein.

PLASMALOGEN COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AND METHODS FOR TREATING DISEASES OF THE AGING

Described herein are routes of synthesis and therapeutic uses of 1-alkyl, 2-acyl glycerol derivatives of formula I: which when administered to mammalian biological systems result in increased cellular concentrations of specific sn-2 substituted ethanolamine plasmalogens independent of the ether lipid synthesis capacity of the system. Elevating levels of the specific sn-2 substituted species in this way can cause lowering of membrane cholesterol levels and the lowering of amyloid secretion. These compounds can be used for the treatment or prevention of diseases of aging associated with increased membrane cholesterol, increased amyloid, and decreased plasmalogen levels, such as neurodegeneration (including Alzheimer''s disease, Parkinson''s disease and age-related macular degeneration), cognitive impairment, dementia, cancer (e.g. prostate, lung, breast, ovarian, and kidney cancers), osteoporosis, bipolar disorder and vascular diseases (such as atherosclerosis, hypercholesterolemia).

Nucleic Acid of Formula (I): GIXmGn, or (II): CIXmCn, in Particular as an Immune-Stimulating Agent/Adjuvant

The present invention relates to a nucleic acid of the general formula (I): GlXmGn, or (II): ClXmCn, which may be modified by a lipid. The nucleic acid of the invention acts as an immune-stimulating agent inducing the innate immune response. The invention relates further to a pharmaceutical composition (in a first embodiment), each containing an immune-stimulating agent according to the invention in combination with a pharmaceutically active carrier/vehicle (and, optionally, further auxiliary substances, additives and/or further adjuvants). In another embodiment, the inventive nucleic acid is combined with at least one pharmaceutically active component, a pharmaceutically acceptable carrier/vehicle (and, optionally, further auxiliary substances, additives and/or further adjuvants). Accordingly, the present invention is directed to a vaccine, which corresponds to a pharmaceutical composition of the invention (second embodiment), wherein the pharmaceutically active component induces a specific immune response (e.g. an antigen). The present invention relates likewise to the use of a nucleic acid of the invention or a pharmaceutical composition according to the invention for the treatment of infectious diseases, autoimmune diseases, allergies or cancer diseases.