82001-53-4

Usage

Uses

Used in Nanotechnology and Molecular Engineering:
12-MERCAPTODODECANOIC ACID is used as a building block for the formation of hydrophilic self-assembled monolayers (SAMs) on gold surfaces. The resulting monolayers, terminated with carboxylic acid groups, can be further functionalized to introduce more complex end groups, allowing for the creation of tailored surfaces with specific properties and functionalities.
Used in Molecular Structure Studies:
12-MERCAPTODODECANOIC ACID has been utilized in a study investigating the effect of molecular structure on the precision of copper-bound α,ω-mercaptoalkanoic acid "molecular ruler" stacks. This research aims to understand how the molecular structure of 12-MERCAPTODODECANOIC ACID and similar compounds can influence the formation and properties of these molecular ruler stacks, which have potential applications in various fields, including electronics, sensors, and materials science.

InChI:InChI=1/C12H24O2S/c13-12(14)10-8-6-4-2-1-3-5-7-9-11-15/h15H,1-11H2,(H,13,14)

Upstream product

• 60908-53-4 12-((ethoxy(thiocarbonyl))thio)dodecanoic acid 
• 352439-40-8 12-acetylsulfanildodecanoic acid 
• 5876-87-9 1,11-dodecadiene 
• 5675-51-4 1,12-dodecandiol 
• 3344-77-2 12-bromododecanol 
• 73367-80-3 12-bromododecanoic acid 

Downstream Products

• 149183-56-2 12-{(11-Carboxy-undecylsulfanyl)-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-methylsulfanyl}-dodecanoic acid 
• 113297-35-1 12-[(11-Carboxy-undecylsulfanyl)-phenyl-methylsulfanyl]-dodecanoic acid 
• 1372802-61-3 C₃₁H₄₇F₄N₃O₄S₂ 

Relevant academic research and scientific papers

SYNTHESIS OF A BIPOLAR PHOSPHATIDYLETHANOLAMINE: A MODEL COMPOUND FOR A MEMBRANE-SPANNING PROBE

A general strategy for the synthesis of membrane-spanning bipolar phospholipids equipped with a reactive functional group probe of the mebrane environment is described.The strategy is exemplified by the synthesis of a biphosphatidylethanolamine that is co

Development of 11C-Labeled ω-sulfhydryl fatty acid tracer for myocardial imaging with PET

[11C]-S-methyl-16-thiopalmitic acid (a) was developed with excellent heart-to-background uptake ratios and higher retention in heart. Myocardial uptake and metabolism of the tracer is markedly higher CPT I dependent. When compared to [11C]-S-methyl-14-thiomyristic acid (b), [11C]-S-methyl-12-thiododecanoic acid (c) and [11C]-palmitate, a showed an early high uptake and a significantly slower late clearance in heart and a prolonged myocardial elimination half-life (30 min). Analysis of heart tissue and urine samples showed that a was metabolized via beta-oxidation in myocardium. Small animal PET images of the accumulation of a in the rat myocardium were clearly superior to [11C]-palmitate. These initial studies suggest that a could be a potentially useful clinical PET tracer to assess myocardial fatty acid metabolism.

A bola-phospholipid bearing tetrafluorophenylazido chromophore as a promising lipid probe for biomembrane photolabeling studies

A bola-phospholipid probe, carrying a tetrafluorophenylazido chromophore in the middle of the transmembrane diacyl chain, was synthesized and characterized with a view to studying biomembranes by a photolabeling approach. This probe shows the advantageous stability of bola-lipids in giant vesicle formation alongside excellent photochemical properties conferred by the tetrafluorophenylazido chromophore, and thus constitutes a promising probe for biomembrane photolabeling studies.

Multiple Electron Tunneling Paths across Self-Assembled Monolayers of Alkanethiols with Attached Ruthenium(II/III) Redox Centers

Alkanethiol monolayers with pendant redox centers are deposited on gold electrodes by selfassembly.The monolayers are composed of both an electroactive thiol, HS(CH2)nC(O)NHCH2pyRu(NH3)5(2+/3+), with 10-15 methylene groups, and a diluent thiol, HS(CH2)mCOOH, also with 10-15 methylene groups.The monolayers are classified as "matched" (n = m), "exposed" ( n = 15, m = 10-14), and "buried" (n = 10, m = 11-15) according to the relative position of the redox center.Cyclic voltammograms in aqueous Na2SO4 indicate that the monolayers are close-packed with the redox centers residing in the aqueous phase in all but the most buried cases.Measurements of electron transfer kinetics by several methods (cyclic voltammetry, ac impedance spectroscopy, chronoamperometry) yield an internally consistent set of kinetic parameters, the standard rate constant ko, and the reorganization energy λ of the redox centers.The reorganization energies are in good agreement with the theoretically predicted value of 1.0 eV for the pyRu(NH3)5 redox centers.Plots of ln(ko) vs m are linear in all three cases.The slopes of the linear regression fit provide tunneling parameters (β, where ko ca. e-βm) of 0.97 +/- 0.03 (matched cases), 0,83 +/- 0.03 (exposed cases) and 0.16 +/- 0.02 (buried cases) per methylene.This pattern of β's is interpreted in terms of electronic coupling between the redox center and the electrode via both the redox thiol and the proximate diluent thiols, with the coupling via the diluent thiols dominating in the exposed cases.

Design, synthesis, and properties of a photoactivatable membrane-spanning phospholipidic probe

We introduce here a new photochemical probe suitable for labeling deep into the hydrophobic core of membranes: bis-phosphatidylethanolamine (trifluoromethyl)phenyldiazirine 19 (DIPETPD). This is a bipolar phospholipid provided with a covalently bonded chain designed to span the membrane and equipped with a centrally defined attachment point for the photolabeling group (trifluoromethyl)phenyldiazirine (TPD). This molecule was designed to enhance the geometrical resolution of photochemical labeling of membrane proteins by locating the photoreactive functionality in the center of the bilayer. The remarkable chemical stability of the photoreactive group TPD1 allowed the design of a straightforward and convergent synthetic strategy. The key steps developed for molecules of this new general kind are (a) the mild and efficient coupling of two moieties of N-tBOC-protected lysophosphatidylethanolamine methyl ester to the photoreactive symmetric dicarboxylic fatty acid mediated by dicyclohexylcarbodiimide and (dimethylamino)pyridine and (b) the smooth deprotection of the phosphate and amino functionalities with sodium iodide and trifluoroacetic acid, respectively, to yield the final product. DIPETPD has been successfully incorporated into small and large unilamellar vesicles of different lipid composition and prepared by a variety of procedures. The bilayer location of this reagent (transmembrane vs 'U'-shaped conformations) was assayed by reaction of the amino groups at the polar heads of the bipolar phospholipid with selected membrane-impermeable reagents. Photolysis of the probe incorporated into vesicles occurs readily upon irradiation with UV light (near 360 nm). These 'loaded' vesicles show adequate stability and appear uniform and unilamellar in electron micrographs. They undergo the fusion reaction with influenza virus as efficiently as reagent-free vesicles. Evidence is presented here that DIPETPD and a reductively methylated form efficiently label the peptide ion channel form of gramicidin A (and a chemical analogue) and the influenza virus hemagglutinin. DIPETPD may help to identify transmembrane regions of integral membrane proteins and map the lipid - protein interface in a region known to be deep in the membrane. A new radioactive version of this reagent ([3H]-DIPETPD)2 has been recently used to ascertain that the HA2 subunit of influenza virus hemagglutinin inserts into the target membrane prior to fusion.