10054-29-2

Usage

Uses

Used in Metalworking Fluids:
Tetradecyl dihydrogen phosphate is used as a surfactant and corrosion inhibitor for enhancing the performance and longevity of metalworking fluids. Its properties help in reducing friction, wear, and corrosion, thus improving the efficiency of machining processes.
Used in Water Treatment Processes:
In the water treatment industry, tetradecyl dihydrogen phosphate serves as a dispersant and antiscalant. It is utilized to control scale formation and improve overall water quality by preventing the precipitation of minerals that can cause scaling and fouling in water systems.
Used in Industrial Formulations:
Due to its versatile properties, tetradecyl dihydrogen phosphate is used as an additive in a wide range of industrial formulations. It contributes to the improvement of product performance by enhancing wetting, dispersion, and reducing foam, which is beneficial in various applications such as cleaning agents, coatings, and personal care products.

InChI:InChI=1/C14H31O4P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-19(15,16)17/h2-14H2,1H3,(H2,15,16,17)

Upstream product

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Relevant academic research and scientific papers

Synthesis of Alkyl Dihydrogenphosphate by the Reaction of Alcohols and Silyl Polyphosphate

Alkyl dihydrogenphosphates were readily prepared by phosphorylation of alcohols with trimethylsilyl polyphosphate of polyphosphorylated silica-gel.

Alkyl and alkoxyethyl antineoplastic phospholipids

Two series of phosphodiester ether lipid analogs with (N- methylmorpholino)ethyl or (N-methylpiperidino)ethyl polar head groups and long aliphatic or alkoxyethyl chains in the nonpolar portion of the molecule were synthesized as potential antineoplastic agents. The cytotoxic activity of these compounds (9-19) was evaluated in vitro against a panel of six human tumor xenografts and in two biochemical, mechanism-based screens (cdc2 kinase and cdc25 phosphatase). Analogs 13, 14, 17, and 19 showed activity in the in vitro tests. Specifically, 14 and 17 were more active than the reference compound hexadecylphosphocholine (Miltefosine, He-PC) while 13 and 19 possessed activity similar to that of the control. Of the analogs tested the one with the highest potency and least toxicity (17) has an N- methylpiperidino head group and a C16 alkyl chain. In the mechanism-based tests 11 showed weak inhibitory activity in the cdc25 phosphatase screen.

Synthesis and biological activity of dialkylphosphocholines

A series of dialkylphosphocholines were prepared and evaluated for their biological activity. The antiprotozoal activity was determined against Acanthamoeba lugdunensis. Compound 15 exhibited excellent trophocidal activity. None of the tested dialkylphosphocholines exhibited better fungicidal activity against Candida albicans than miltefosine. The antineoplastic activity was determined against HeLa. The most cytotoxic was compound 10, which was more active against tumor cells as against normal cells.

Phospholipid-induced aggregation and anthracene excimer formation

(Chemical Equation) The zinc complex of anthryl bis(dipicolylamine) (1) aggregates upon binding with long-chain aliphatic phosphates and displays anthracene excimer fluorescence, which provides a new strategy toward detection of the biologically important lysophosphatidic acid in aqueous solution.

Fatty alcohol phosphates are subtype-selective agonists and antagonists of lysophosphatidic acid receptors

A more complete understanding of the physiological and pathological role of lysophosphatidic acid (LPA) requires receptor subtype-specific agonists and antagonists. Here, we report the synthesis and pharmacological characterization of fatty alcohol phosphates (FAP) containing saturated hydrocarbon chains from 4 to 22 carbons in length. Selection of FAP as the lead structure was based on computational modeling as a minimal structure that satisfies the two-point pharmacophore developed earlier for the interaction of LPA with its receptors. Decyl and dodecyl FAPs (FAP-10 and FAP-12) were specific agonists of LPA2 (EC50 = 3.7 ± 0.2 μM and 700 ± 22 nM, respectively), yet selective antagonists of LPA3 (Ki = 90 nM for FAP-12) and FAP-12 was a weak antagonist of LPA1. Neither LPA1 nor LPA3 receptors were activated by FAPs; in contrast, LPA2 was activated by FAPs with carbon chains between 10 and 14. Computational modeling was used to evaluate the interaction between individual FAPs (8 to 18) with LPA2 by docking each compound in the LPA binding site. FAP-12 displayed the lowest docked energy, consistent with its lower observed EC50. The inhibitory effect of FAP showed a strong hydrocarbon chain length dependence with C12 being optimum in the Xenopus laevis oocytes and in LPA3-expressing RH7777 cells. FAP-12 did not activate or interfere with several other G-protein-coupled receptors, including S1P-induced responses through S1P1.2,3.5 receptors. These data suggest that FAPs are ligands of LPA receptors and that FAP-10 and FAP-12 are the first receptor subtype-specific agonists for LPA2.