645-72-7

Usage

Uses

Used in Chemical Synthesis:
3,7,11,15-Tetramethylhexadecan-1-ol is used as an intermediate in the synthesis of various organic compounds, including phytane (P399005). Phytane is a useful intermediate involved in the manufacturing and analysis of different compounds.
Used in Lubricant Industry:
3,7,11,15-Tetramethylhexadecan-1-ol is used as a component in the development of stable and environmentally-friendly lubricating oils. Its unique chemical structure and properties make it suitable for improving the performance and reducing the environmental impact of lubricants.

InChI:InChI=1/C20H42O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h17-21H,6-16H2,1-5H3

Upstream product

• 7541-49-3 3,7,11,15-tetramethyl-2-hexadecen-1-ol 
• 14721-66-5 phytanic acid 
• 253686-88-3 (E)-3,7,11,15-tetramethylhexadec-2-en-1-ol 
• 7664-93-9 sulfuric acid 
• 60-29-7 diethyl ether 
• 150-86-7 phytol 
• 102464-52-8 2,6,10,14-Tetramethyl-pentadecanon-⁽¹²⁾-carbonsaeure-⁽¹⁾ 
• 102899-50-3 2,6,10,14-Tetramethyl-pentadecanon-⁽¹²⁾-carbonsaeure-⁽¹⁾-methylester 
• 72720-15-1 2,6,10,14-tetramethyl-1-hexadecanol 

Downstream Products

• 2791-57-3 phytanyl bromide 
• 14721-66-5 phytanic acid 
• 115606-41-2 Azobenzolcarbonsaeure-⁽⁴⁾-dihydrophytylester 
• 100566-23-2 dihydrophytyl tosylate 
• 1921-70-6 pristane 
• 2140-82-1 2,6,10,14-tetramethyl-1-pentadecene 
• 638-36-8 phytane 
• 532426-78-1 (2E)-3,7,11,15-tetramethyl-2-hexadecene 
• 314740-79-9 phosphorous acid benzyl ester 2-cyano-ethyl ester 3,7,11,15-tetramethyl-hexadecyl ester 
• 6297-03-6 19-oxaheptatriacontane 
• 314740-80-2 benzyl 2-cyanoethyl 3,7,11,15-tetramethylhexadecylphosphate 
• 316187-61-8 benzyl 3,7,11,15-tetramethylhexadecylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 
• 10339-79-4 4,8,12,16-tetramethylheptadecanoic acid 
• 1042667-57-1 phenyl phytanyl H-phosphonate 

Relevant academic research and scientific papers

Comparison of the supramolecular structures of two glyco lipids with chiral and nonchiral methyl-branched alkyl chains from natural sources

Two alkyl glycosides with the same type of disaccharide headgroups (melibiose) and different methyl-branched alkyl chains, short chiral [(2R,4R,6R,8R)-2,4,6,8-tetramethyldecyl, extracted from an animal source] and long nonchiral (3,7,11,15-tetramethylhexadecyl, from a plant source), were synthesized. The supramolecular aggregate structure formed in dilute solutions was investigated by small-angle neutron scattering and surface tension measurements. The lyotropic phase diagram was studied by differential scanning calorimetry and water penetration scans. The thermotropic phase behavior was investigated by polarizing microscopy. The compounds showed unusual phase behavior: (i) The liquid-crystalline polymorphism is reduced to only form smectic A phases in the pure state; the formation of lyotropic phases such as hexagonal or lamellar phases was not observed, (ii) The compound with the longer nonchiral alkyl chain is more soluble in water than the one with the shorter chiral chain, most likely because of the different flexibilities of the chains, (iii) For the long-chain compound, the formation of micelles is observed, whereas the short-chain compound forms large disklike/bilayer aggregates. The method of methylation of the chain controls the self-assembly and can explain different biological functions for either plants (variable temperature) or animals (constant temperature).

Aggregation of synthetic zinc chlorins with several esterified alkyl chains as models of bacteriochlorophyll-c homologs

Zinc complexes of 3-hydroxymethyl-13-oxochlorin possessing several branched alkyl chains as an esterified group at the 17-position were systematically prepared. In non-polar organic solvents, these compounds aggregated to form oligomers absorbing up to 800-nm light with around a 740-nm peak, which are good models for bacteriochlorophylls-c and d, extramembranous antenna pigments of photosynthetic green bacteria. All the visible spectra of the in-vitro oligomers are the same and the esterified alcohols induced no effect on the local structure of the oligomers. The circular dichroism spectra changed with elongation of esterified alkyl chains, which resulted in the similar spectra to the in-vivo oligomers. Esterified alcohols should subtly affect the supramolecular structure and/or stability of the self-aggregates.

Phosphoramidite reagent and applications thereof in oligonucleotide synthesis

The invention provides a phosphoramidite reagent and applications thereof. According to the invention, the phosphoramidite reagent is a 2-nitrile ethoxy phosphoramidite compound with a large non-polarsubstituent group on a 2-nitrile ethoxy group, and can react with a nucleoside monomer or a nucleotide fragment 3'-OH or 5'-OH to generate phosphoramidite diester, the phosphoramidite diester continuously reacts with another group of nucleoside monomers or nucleotide fragments 3'-OH or 5'-OH under the action of a proper activating agent to generate phosphoramidite trimester, oxidizing or vulcanizing is performed to obtain phosphoric acid triester or thiophosphoric acid trimester, and deprotection is performed to obtain oligonucleotides, wherein in the whole process, all phosphite intermediates or phosphate intermediates are easily dissolved in a solvent with medium and low polarity and have low solubility in a high-polar solvent while other reaction raw materials or by-products are easilydissolved in the high-polar solvent, such that the purification can be performed through non-polar/polar solvent extraction so as not to hinder the subsequent chain propagation reaction; the method is suitable for one-by-one nucleotide linking and reactions linked by a fragment method.

Discovery of Lipophilic Bisphosphonates That Target Bacterial Cell Wall and Quinone Biosynthesis

We report that alkyl-substituted bisphosphonates have activity against Bacillus anthracis Sterne (0.40 μg/mL), Mycobacterium smegmatis (1.4 μg/mL), Bacillus subtilis (1.0 μg/mL), and Staphylococcus aureus (13 μg/mL). In many cases, there is no effect of serum binding, as well as low activity against a human embryonic kidney cell line. Targeting of isoprenoid biosynthesis is involved with 74 having IC50 values of ～100 nM against heptaprenyl diphosphate synthase and 200 nM against farnesyl diphosphate synthase. B. subtilis growth inhibition was rescued by addition of farnesyl diphosphate, menaquinone-4 (MK-4), or undecaprenyl phosphate (UP), and the combination of MK-4 and UP resulted in a 25× increase in ED50, indicating targeting of both quinone and cell wall biosynthesis. Clostridioides difficile was inhibited by 74, and since this organism does not synthesize quinones, cell wall biosynthesis is the likely target. We also solved three X-ray structures of inhibitors bound to octaprenyl diphosphate and/or undecaprenyl diphosphate synthases.

AMPHIPHILE PRODRUGS

Amphiphilic prodrugs of general formula A-X are disclosed, wherein A is a biologically active agent or may be metabolised to a biologically active agent; and X is selected from the group consisting of R, or up to three R moieties attached to a linker, Y1, Y2 or Y3, wherein R is selected from a group consisting of alkyl, alkenyl, alkynyl, branched alkyl, branched alkenyl, branched alkynyl, substituted alkyl, substituted alkenyl and substituted alkynyl groups and their analogues; Y1 is a linker group which covalently attached to an R group at one site and is attached to A at a further independent site; Y2 is a linker group which is covalently attached to two R groups at two independent sites and is attached to A at a further independent site; and Y3 is a linker group which is covalently attached to three R groups at three independent sites and is attached to A at a further independent site. Self-assembly of the amphiphilic prodrugs into reverse lyotropic phases, particularly hexagonal, cubic and sponge, is disclosed. In preferred embodiments A is dopamine or a 5-fluorouracil prodrug.

COMPOSITIONS IN THE FORM OF AN INJECTABLE AQUEOUS SOLUTION COMPRISING AMYLIN, AN AMYLIN RECEPTOR AGONIST OR AN AMYLIN ANALOGUE AND A CO-POLYAMINO ACID

A composition in the form of an injectable aqueous solution, the pH of which is comprised from 6.0 to 8.0, including at least: a) amylin, an amylin receptor agonist or an amylin analogue;b) a co-polyamino acid bearing carboxylate charges and hydrophobic radicals Hy, said co-polyamino acid being constituted of glutamic or aspartic units and said hydrophobic radicals Hy being according to formula I below: [in-line-formulae]*?GpR?r?GpA?a?GpC)p ??Formula I[/in-line-formulae] wherein the composition does not comprise a basal insulin the isoelectric point pI of which is comprised from 5.8 to 8.5. It also relates to a composition wherein it further includes prandial insulin.

COMPOSITIONS SOUS FORME D'UNE SOLUTION AQUEUSE INJECTABLE COMPRENANT DU GLUCAGON HUMAIN ET UN CO-POLYAMINOACIDE

Physically stable compositions in the form of an injectable aqueous solution, wherein the pH is from 6.0 to 8.0, includes at least: a) human glucagon andb) a co-polyamino acid bearing carboxylate charges and hydrophobic radicals Hy. In one embodiment, the compositions further comprise a gut hormone.

INJECTABLE SOLUTION AT PH 7 COMPRISING AT LEAST ONE BASAL INSULIN WHEREIN THE PI IS COMPRISED FORM 5.8 TO 8.5 AND A CO-POLYAMINO ACID BEARING CARBOXYLATE CHARGES AND HYDROPHOBIC RADICALS

In one embodiment, the composition according to the invention is characterized in that the co-polyamino acid bearing carboxylate charges and at least one hydrophobic radical -Hy is chosen among the co-polyamino acids according to formula XXXb hereinafter: wherein, D represents, independently, either a group —CH2— (aspartic acid) or a group —CH2—CH2— (glutamic acid),X represents a cationic entity chosen in the group comprising alkali cations,Rb and Rb′, identical or different, are either a hydrophobic radical -Hy, or a radical chosen in the group consisting of an H, a C2 to C10 linear acyl group, a C3 to C10 branched acyl group, a benzyl, a terminal “amino acid” unit and a pyroglutamate, at least one of Rb and R′b is a hydrophobic radical -Hy,Q and Hy are as defined above.n+m represents the degree of polymerization DP of the co-polyamino acid, namely the mean number of monomeric units per co-polyamino acid chain and 5≤n+m≤250.

COMPOSITIONS IN THE FORM OF AN INJECTALE AQUEOUS SOLUTION COMPRISING HUMAN GLUCAGON AND A CO-POLYAMINO ACID

Physically stable compositions in the form of an injectable aqueous solution, the pH of which is comprised from 6.0 to 8.0, having at least: human glucagon and a co-polyamino acid bearing carboxylate charges and hydrophobic radicals Hy, in one embodiment, the compositions according to the invention further includes a gastrointestinal hormone.

Chemically Stable Lipids for Membrane Protein Crystallization

The lipidic cubic phase (LCP) has been widely recognized as a promising membrane-mimicking matrix for biophysical studies of membrane proteins and their crystallization in a lipidic environment. Application of this material to a wide variety of membrane proteins, however, is hindered due to a limited number of available host lipids, mostly monoacylglycerols (MAGs). Here, we designed, synthesized, and characterized a series of chemically stable lipids resistant to hydrolysis, with properties complementary to the widely used MAGs. In order to assess their potential to serve as host lipids for crystallization, we characterized the phase properties and lattice parameters of mesophases made of two most promising lipids at a variety of different conditions by polarized light microscopy and small-angle X-ray scattering. Both lipids showed remarkable chemical stability and an extended LCP region in the phase diagram covering a wide range of temperatures down to 4 °C. One of these lipids has been used for crystallization and structure determination of a prototypical membrane protein bacteriorhodopsin at 4 and 20 °C.