3539-43-3

Basic information

• Product Name: AMPHISOL A
• Synonyms: AMPHISOL A;PHOSPHORICMONOHEXADECYL ESTER;1-hexadecanol,dihydrogenphosphate;1-Hexadecanol,dihydrogenphosphate(and)diethanolaminecetylphosphate;cetylphosphate;Cetylphosphate(and)dea-cetylphosphate;hexadecylphosphate;hexadecyl dihydrogen phosphate
• CAS NO: 3539-43-3
• Molecular Formula: C₁₆H₃₅O₄P
• Molecular Weight: 322.42
• EINECS: 222-581-1
• Product Categories: Surfactant
• Mol File: 3539-43-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 71 °C
• Boiling Point: 439.8 °C at 760 mmHg
• Flash Point: 219.8 °C
• Appearance: /
• Density: 1.013 g/cm³
• Vapor Pressure: 5.8E-09mmHg at 25°C
• Refractive Index: 1.464
• PKA: 1.95±0.10(Predicted)
• Water Solubility: 1mg/L at 25℃
• CAS DataBase Reference: AMPHISOL A(CAS DataBase Reference)
• NIST Chemistry Reference: AMPHISOL A(3539-43-3)
• EPA Substance Registry System: AMPHISOL A(3539-43-3)

Safety Data

• Hazardous Substances Data: 3539-43-3(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C16H35O4P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-21(17,18)19/h2-16H2,1H3,(H2,17,18,19)

Upstream product

• 67-66-3 chloroform 
• 36653-82-4 1-Hexadecanol 
• 4697-37-4 ethyl metaphosphate 
• 107-46-0 Hexamethyldisiloxane 
• 58527-29-0 hexadecyl dichlorophosphinate 
• 10025-87-3 trichlorophosphate 
• 181762-88-9 Phosphoric acid bis-(2-cyano-ethyl) ester hexadecyl ester 
• 56827-92-0 n-hexadecyl diphenyl phosphonate 

Downstream Products

• 82300-59-2 Phosphoric acid hexadecyl ester (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 93605-01-7 P¹-(1-hexadecyl)-P²-(1-β-D-arabinofuranosylcytosin-5'-yl)pyrophosphate 
• 1448798-75-1 2-[benzyl(dimethyl)ammonio]ethyl hexadecyl phosphate 
• 1448798-76-2 2-[benzyl(dimethyl)ammonio]propyl hexadecyl phosphate 
• 736906-37-9 Phosphoric acid 4-benzyloxy-cyclohexyl ester hexadecyl ester 

Relevant articles and documents

Physicochemical studies on adsorption of monocetyl phosphate salts at the water surface

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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.

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.