59101-28-9

Usage

Uses

Used in Organic Synthesis:
16-Bromohexadecanol is used as an intermediate in the synthesis of various organic compounds, contributing to the creation of a wide range of chemical products.
Used as a Surfactant or Emulsifier in Industrial Applications:
Leveraging its chemical properties, 16-Bromohexadecanol is utilized as a surfactant or emulsifier, playing a crucial role in stabilizing mixtures of different substances in various industrial processes.
Used in Pharmaceutical Industry:
Due to its unique chemical structure, 16-Bromohexadecanol may be employed in the development of pharmaceuticals, potentially enhancing drug formulations or serving as a component in novel therapeutic agents.
Used in Cosmetics Industry:
In the cosmetics field, 16-Bromohexadecanol could be used for its emulsifying properties, helping to create stable formulations for a variety of cosmetic products.
Used in Materials Science:
16-Bromohexadecanol's potential applications in materials science could include its use in the development of new materials with specific properties, such as improved stability or reactivity.

InChI:InChI=1/C16H33BrO/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18/h18H,1-16H2

Upstream product

• 26825-89-8 methyl 16-bromohexadecanoate 
• 505-54-4 thapsic acid 
• 7735-42-4 1,16-hexadecanediol 
• 7370-44-7 5-hexadecanolide 
• 2536-35-8 16-bromohexadecanoic acid 
• 109-29-5 15-hexadecanolide 
• 21964-51-2 hexadeca-1,15-diene 
• 36575-67-4 16-hydroxyhexadecanoic acid methyl ester 

Downstream Products

• 59100-03-7 4-(16-Hydroxy-hexadecyloxy)-benzoic acid methyl ester 
• 109183-03-1 (E)-But-2-enedioic acid 16-bromo-hexadecyl ester ethyl ester 
• 651034-07-0 16-bromohexadecanal 
• 2536-35-8 16-bromohexadecanoic acid 
• 69506-08-7 17-(p-Methoxyphenyl)heptadecan-1-ol 
• 85756-62-3 dotriacontane-1,32-diol 
• 618099-74-4 1,32-bis(tetrahydropyranyloxy)dotriacontane 
• 887604-07-1 octadec-17-ynyloxymethyl-benzene 
• 887604-27-5 Q₂FA₁₈ 
• 887604-32-2 Q₃FA₁₈ 
• 887604-12-8 2-(18-Benzyloxy-octadec-1-ynyl)-1,4-dimethoxy-benzene 
• 887604-17-3 1-(18-Benzyloxy-octadec-1-ynyl)-2,4,5-trimethoxy-benzene 
• 887604-22-0 1-(18-Benzyloxy-octadec-1-ynyl)-2,3,4,5-tetramethoxy-benzene 
• 139041-97-7 thioacetic acid R,S-(16-cyanohexadecyl) ester 

Relevant academic research and scientific papers

Pachychalines A-C: Novel 3-alkylpyridinium salts from the marine sponge Pachychalina sp.

Three 3-alkylpyridinium salts, pachychalines A (1), B (2) and C (3), were isolated from the Caribbean marine sponge Pachychalina sp. (order Haplosclerida). They are the first examples of 3-(aminoalkyl)pyridinium salts. Their chemical structures were elucidated by NMR spectroscopy and detailed ESI HRMS-MS analysis. The total synthesis of 1 allowed the confirmation of the unusual C-C connection between both pyridinium moieties. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Palladium-Catalyzed Long-Range Deconjugative Isomerization of Highly Substituted α,β-Unsaturated Carbonyl Compounds

The long-range deconjugative isomerization of a broad range of α,β-unsaturated amides, esters, and ketones by an in situ generated palladium hydride catalyst is described. This redox-economical process is triggered by a hydrometalation event and is thermodynamically driven by the refunctionalization of a primary or a secondary alcohol into an aldehyde or a ketone. Di-, tri-, and tetrasubstituted carbon-carbon double bonds react with similar efficiency; the system is tolerant toward a variety of functional groups, and olefin migration can be sustained over 30 carbon atoms. The refunctionalized products are usually isolated in good to excellent yield. Mechanistic investigations are in support of a chain-walking process consisting of repeated migratory insertions and β-H eliminations. The bidirectionality of the isomerization reaction was established by isotopic labeling experiments using a substrate with a double bond isolated from both terminal functions. The palladium hydride was also found to be directly involved in the product-forming tautomerization step. The ambiphilic character of the in situ generated [Pd-H] was demonstrated using isomeric trisubstituted α,β-unsaturated esters. Finally, the high levels of enantioselectivity obtained in the isomerization of a small set of α-substituted α,β-unsaturated ketones augur well for the successful development of an enantioselective version of this unconventional isomerization.

Scalable Synthesis of Human Ultralong Chain Ceramides

Ceramides with ultralong chains (≥30 carbons), also known as acylceramides, play a critical role in the survival of mammals on dry land. An efficient and scalable synthesis of four major classes of ultralong human skin ceramides is reported. The key approach involves the use of a succinimidyl ester that acts as a protective group, helps overcome the extremely low solubility, and simultaneously activates the fatty acid for its clean and high-yielding attachment to a sphingoid base.

Conformationally-locked N -glycosides: Exploiting long-range non-glycone interactions in the design of pharmacological chaperones for Gaucher disease

Pyranoid-type glycomimetics having a cis-1,2-fused glucopyranose-2-alkylsulfanyl-1,3-oxazoline (Glc-PSO) structure exhibit an unprecedented specificity as inhibitors of mammalian β-glucosidase. Notably, their inhibitory potency against human β-glucocerebrosidase (GCase) was found to be strongly dependent on the nature of aglycone-type moieties attached at the sulfur atom. In the particular case of υ-substituted hexadecyl chains, an amazing influence of the terminal group was observed. A comparative study on a series of Glc-PSO derivatives suggests that hydrogen bond acceptor functionalities, e.g. fluoro or methyloxycarbonyl, significantly stabilize the Glc-PSO:GCase complex. The S-(16-fluorohexadecyl)-PSO glycomimetic turned out to be a more potent GCase competitive inhibitor than ambroxol, a non glycomimetic drug currently in pilot trials as a pharmacological chaperone for Gaucher disease. Moreover, the inhibition constant increased by one order of magnitude when shifting from neutral (pH 7) to acidic (pH 5) media, a favorable characteristic for a chaperone candidate. Indeed, the fluoro-PSO derivative also proved superior to ambroxol in mutant GCase activity enhancement assays in N370S/N370S Gaucher fibroblasts. The results presented here represent a proof of concept of the potential of exploiting long-range non-glycone interactions for the optimization of glycosidase inhibitors with chaperone activity.

Synthesis of new ligands for targeting the S1P1 receptor

Sphingosine-1-phosphate (S1P) influences various fundamental biological processes by interacting with a family of five G protein-coupled receptors (S1P1-5). FTY720, a sphingosine analogue, which was approved for treatment of relapsing forms of multiple sclerosis, is phosphorylated in vivo and acts as an agonist of four of the five S1P receptor subtypes. Starting from these lead structures we developed new agonists for the S1P1 receptor. The biological activity was tested in vivo and promising ligands were fluorinated at different positions to identify candidates for positron emission tomography (PET) imaging after [18F]-labelling. The radioligands shall enable the imaging of S1P1 receptor expression in vivo and thus may serve as novel imaging markers of S1P-related diseases.

ANTIMICROBIAL MONOMERS FOR USE IN DENTAL POLYMERS

Antimicrobial compounds are provided that are polymerizable. The compounds include monomers with antimicrobial properties. The compounds have cross-linking properties and are hydrolytically stable. The compounds may be utilized in dental and/or medical applications, including dental composites, dentures, bonding agents, sealants, resins and medical devices.

BASELESS NUCLEOTIDE ANALOGUES AND USES THEREOF

A method of detecting a target nucleic acid.

NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES

The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.

NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES

The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.

Maltoside and Phosphocholine Derivatives, Uses thereof and Methods of Preparing Artificial Lipid Structures Thereof

Disclosed are saccharide and phosphocholine derivatives. The derivatives include azide and alkyne derivatives which form one end of a variable length carbon chain. The opposite end of the variable length carbon chain is covalently linked to the saccharide or phosphocholine. The saccharide may be, for instance, a maltoside. The alkyne and azide derivatives of the saccharides and phosphocholine may be reacted together to form amphiphilic molecules useful in cellular membrane studies and applications. By adjusting the length of the carbon chain, the biochemical and biophysical properties of the resultant 1,4-disubstituted 1,2,3-triazole compounds may be custom tailored for the intended application. Resultant molecules may form micelles, bicelle, lipid bilayers and other like structures useful in the isolation and purification of membrane bound or membrane associated proteins and biochemical components. The saccharides and phosphocholine molecules may be alternatively substituted as desired to provide additional flexibility in designing the desired end product.