2136-72-3

Usage

Uses

Used in the Chemical Industry:
2-(OCTADECYLOXY)ETHANOL is used as a precursor for the synthesis of fatty alcohol ethoxylates through the etherification process. This process involves the reaction of fatty alcohol with ethylene glycol, resulting in the formation of ethoxylates, which are widely used as nonionic surfactants in various applications.
Used in the Cosmetics and Personal Care Industry:
In the cosmetics and personal care industry, 2-(OCTADECYLOXY)ETHANOL is used as an emollient, providing a smooth and soft texture to the skin. Its amphiphilic nature allows it to form a protective layer on the skin, helping to retain moisture and improve skin hydration.
Used in the Pharmaceutical Industry:
2-(OCTADECYLOXY)ETHANOL can be utilized as a component in the formulation of drug delivery systems, particularly for hydrophobic drugs. Its ability to form micelles or liposomes can enhance the solubility and bioavailability of these drugs, improving their therapeutic efficacy.
Used in the Textile Industry:
In the textile industry, 2-(OCTADECYLOXY)ETHANOL is employed as a surfactant in the processing of fibers and fabrics. Its surfactant properties help to reduce surface tension, allowing for better wetting and penetration of the fibers, which can improve the efficiency of dyeing and finishing processes.
Used in the Agrochemical Industry:
2-(OCTADECYLOXY)ETHANOL can be used as an adjuvant in the agrochemical industry, particularly for the formulation of pesticides and herbicides. Its amphiphilic properties can enhance the spread and adherence of these chemicals on plant surfaces, improving their effectiveness in controlling pests and weeds.

Synthesis

Respectively, to take propylene glycol 680mg, sodium hydrogen 2.5g added to 100 ml round bottom flask,THF was added to 10 ml of a solution and stirred for 30 minutes,Then raise the temperature to reflux for 1 hour,And then weigh the bromo-octadecane dispersed in 10 ml of THF by adding a separatory funnel and dropping into the reaction solution,After refluxing the reaction overnight. After completion of the reaction, a saturated sodium chloride solution was added,Dichloromethane extraction three times, combined extract, filter evaporated solvent, crude column chromatography separation,The second band was collected, the resulting product, 550 mg, yield 17.1%.

Upstream product

• 3386-32-1 n-octadecyl p-toluenesulfonate 
• 107-21-1 ethylene glycol 
• 6064-94-4 methyl octadecyloxyacetate 
• 31081-59-1 1-octadecyl methanesulfonate 
• 112-89-0 1-Bromooctadecane 
• 112-92-5 1-octadecanol 
• 22739-42-0 Acetic acid 2-octadecyloxy-ethyl ester 

Downstream Products

• 16198-75-7 sulfuric acid mono-(2-octadecyloxy-ethyl) ester 
• 130705-28-1 2-(octadecyloxy)ethyl dihydrogen phosphate 
• 16057-43-5 2-(2-n-octadecyloxyethoxy)ethanol 

Relevant academic research and scientific papers

Lipid modified spermine derivatives and the use of the derivatives of the prepared liposome

The invention provides a liposome-modified spermine derivative and a liposome prepared by the derivative. The spermine derivative is directly applied or is mixed with one or more selected from cholesterol, neutral lipids and polyethylene glycol (PEG)-modified lipids, which can be adopted as a carrier for entrapping or absorbing bioactive molecular drugs to be loaded into cells. In this way, the effect of regulation, intervention or treatment is realized. In a general formula (1), X1 represents -(CH2)- or carbonyl group, wherein n represents 1, 2 or 3; X2 represents -(CH2)-, ester group, amide group, oxygen, or sulfur; R1 and R2 independently represent C6-C18 alkyl group or lipophilic cholesterol molecules, respectively.

Combinatorial synthesis of PEG oligomer libraries

A simple chain-extending approach was established for the scale-up of the monoprotected monodisperse PEG diol materials. Reactions of THP-(OCH2CH2)n—OMs (n=4, 8, 12) with a large excess of commercially available H—(OCH2CH2)n—OH (n=1-4) under basic conditions led to THP-(OCH2CH2)n—OH (n=5-15). Similarly, Me-(OCH2CH2)n—OH (n=4-11, 13) were prepared from Me-(OCH2CH2)n—OMs (n=3, 7, 11). For the chain elongation steps, 40-80% yields were achieved through extraction purification. PEG oligomer libraries I and II were generated in 50-95% overall yields by alkylation or acylation of THP-(OCH2CH2)n—OH (n=1-15) followed by deprotection. Alkylation of Me-(OCH2CH2)n—OH (n=1-11, 13) with X—(CH2)m—CO2R (X=Br or OMs) and subsequent hydrolysis led to PEG oligomer library III in 30-60% overall yields. Combinatorial purification techniques were adapted to the larger-scale library synthesis. A total of 498 compounds, each with a weight of 2-5 g and a minimum purity of 90%, were synthesized.

Anchor dependency for non-glycerol based cationic lipofectins: Mixed bag of regular and anomalous transfection profiles

Although detailed structure-activity, physicochemical and biophysical investigations in probing the anchor influence in liposomal gene delivery have been reported for glycerol-based transfection lipids, the corresponding investigation for non-glycerol based simple monocationic transfection lipids have not yet been undertaken. Towards this end, herein, we delineate our structure-activity and physicochemical approach in deciphering the anchor dependency in liposomal gene delivery using fifteen new structural analogues (lipids 1-15) of recently reported non-glycerol based monocationic transfection lipids. The C14 analogues in both series 1 (lipids 1-6) and series 2 (lipids 7-15) showed maximum efficiency in transfecting COS-1 and CHO cells. However, the C12 analogue of the ether series (lipid 3) exhibited a seemingly anomalous behavior compared with its transfection efficient C10 and C14 analogues (lipids 2 and 4) in being completely inefficient to transfect both COS-1 and CHO cells. The present structure-activity investigation also convincingly demonstrates that enhancement of transfection efficiencies through incorporation of membrane re-organizing unsaturation elements in the hydrophobic anchor of cationic lipids is not universal but cell dependent. The strength of the interaction of lipids 1-15 with DNA was assessed by their ability to exclude ethidium bromide bound to the DNA. Cationic lipids with long hydrophobic tails were found, in general, to be efficient in excluding EtBr from DNA. Gel to liquid crystalline transition temperatures of the lipids was measured by fluorescence anisotropy measurement technique. In general (lipid 2 being an exception), transfection efficient lipids were found to have their mid transition temperatures at or below physiological temperatures (37°C).

Synthesis of Hydroxyethyl Ethers from Long Chain Fatty Alcohols

A two-step facile synthesis of mono- and di-β-hydroxyethyl ethers of long chain fatty alcohols starting from alcohols and chloro/bromo acetic esters is described.These compounds, which are otherwise difficult to obtain in pure state, are of great interest as plant groth promoters.

Phospholipid compound

The present invention provides phospholipids of the general formula: STR1 wherein X is a valency bond, an oxygen or sulphur atom or a sulfonyl, sulfinyl, phenylene, cycloaklylene, carbonylamino, aminocarbonyl, ureido or carbonyl group, R1 is a hydrogen atom or a straight-chained or branched, saturated or unsaturated aliphatic hydrocarbon radical containing up to 18 carbon atoms, which is optionally substituted one or more times by halogen, alkoxy, alkylthio, alkanesulfinyl, alkanesulfonyl, carbalkoxy or phenyl, R2 is a straight-chained or branched, saturated or unsaturated divalent aliphatic hydrocarbon radical containing up to 18 carbon atoms, which is optionally substituted one or more times by halogen, alkoxy, alkylthio, alkanesulphinyl, alkanesulphonyl, carbalkoxy or phenyl, Y is an oxygen atom or a --O--CO--O--, --O--CO--NH-- or --O--CS--NH-- group, R3 is a straight-chained or branched, saturated or unsaturated divalent aliphatic hydrocarbon radical containing 2 to 8 carbon atoms, which can also be part of a cycloalkane ring system and is optionally substituted one or more times by hydroxyl, halogen, alkylthio, alkanesulphinyl, alkanesulfonyl, nitrile, alkoxycarbonyl, carboxamido optionally substituted by alkyl radicals, cycoalkyl, optionally substituted phenyl or alkoxy, which in turn is optionally substituted by phenyl, hydroxyl, alkoxy, alkylthio, alkanesulfinyl, alkanesulfonyl, optionally acylated amino, alkoxycarbonyl, nitrile or carboxamido optionally substituted by alkyl radicals, Z is an oxygen or sulfur atom, R4 is a straight-chained or branched alkylene radical containing 2 to 5 carbon atoms and R5 is a hydrogen atom or a lower alkyl radical, with the proviso that when X is a valency bond, R1 and R2 together represent an unsubstituted, straight-chained or branched, saturated or unsaturated divalent aliphatic hydrocarbon chain containing up to 18 carbon atoms, Y, R4 and R5 have the above-given meanings and Z is an oxygen atom, R3 cannot be a propylene or 2-methylpropylene chain optionally substituted by hydroxyl, alkoxy or benzyloxy and with the proviso that when X is a valency bond, R1 and R2 together signify an alkyl radical containing up to 18 carbon atoms and substituted by halogen or phenyl, Y and Z are oxygen atoms and R4 and R5 have the above-given meanings, R3 cannot be a propylene or 2-hydroxypropylene chain; and the pharmacologically acceptable salts thereof. The invention also provides pharmaceutical compositions containing such compounds, having cancerostatic action without inducing thrombocyte aggregation.

HETEROANALOGUES OF 1-TRIACONTANOL

A synthesis of twelve heteroanalogues II-XIII of the plant growth stimulator 1-triacontanol (I), derived from the parent alcohol by a replacement of 1-4 methylene units by heteroatoms O,S,NH and/or by a replacement of 1-2 ethylene units by -CO-O-, -CO-NH- or groups is reported.Spectral and gas-chromatographic properties (Kovats retention indices) of the compounds are described.