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Hexadecylphosphorylcholine

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Identification
Molecular formula
C21H46NO4P
CAS number
4313-03-5
IUPAC name
hexadecyl 2-(trimethylammonio)ethyl phosphate
State
State

This compound is typically a solid at room temperature, exhibiting waxy and crystalline characteristics.

Melting point (Celsius)
93.00
Melting point (Kelvin)
366.15
Boiling point (Celsius)
460.00
Boiling point (Kelvin)
733.15
General information
Molecular weight
367.65g/mol
Molar mass
367.6460g/mol
Density
0.9570g/cm3
Appearence

Hexadecylphosphorylcholine appears as a colorless to pale yellow solid. It is often presented in a crystalline form and is waxy in nature when at room temperature.

Comment on solubility

Solubility of Hexadecyl 2-(trimethylammonio)ethyl Phosphate

Hexadecyl 2-(trimethylammonio)ethyl phosphate, with the chemical formula C21H46NO4P, is an intriguing compound in terms of its solubility. This quaternary ammonium compound exhibits unique solubility characteristics which are primarily influenced by its hydrophobic and hydrophilic regions. Here are some significant points to consider:

  • Hydrophobic Tail: The long hexadecyl chain contributes significantly to the compound's overall hydrophobicity, leading to poor solubility in water.
  • Hydrophilic Head: The presence of the trimethylammonio and phosphate functional groups enhances its solubility in polar solvents.
  • Amphiphilic Nature: As an amphiphilic molecule, it can solubilize to a certain extent in both polar and non-polar environments, making it useful in various applications.
  • Solution Behavior: When mixed with water, it can form micelles or vesicles, thus suggesting that while it may not be fully soluble, it can interact dynamically with water.
  • Temperature Influence: Solubility can also vary with temperature, as higher temperatures typically increase solubility in many cases.

In conclusion, while hexadecyl 2-(trimethylammonio)ethyl phosphate is not completely water-soluble due to its long hydrocarbon chain, its unique molecular structure allows for interesting dissolution behaviors in various solvents, especially in the formation of micelles in aqueous solutions. This dual nature highlights its potential utility across different chemical and pharmaceutical applications.

Interesting facts

Interesting Facts about Hexadecyl 2-(Trimethylammonio)ethyl Phosphate

Hexadecyl 2-(trimethylammonio)ethyl phosphate is a fascinating compound that finds various applications in both science and industry. It belongs to a class of chemicals known as phospholipids, which are vital components of cell membranes in living organisms. Here are some intriguing aspects of this compound:

  • Cationic Surfactant: This compound is classified as a cationic surfactant. It possesses a positively charged head group, which enhances its ability to interact with negatively charged surfaces, making it useful in numerous applications such as cosmetics and pharmaceuticals.
  • Emulsification Agent: Hexadecyl 2-(trimethylammonio)ethyl phosphate serves as an effective emulsifier. It helps stabilize emulsions by reducing the surface tension between oil and water phases, which is essential for products that require a consistent mixture, such as lotions and creams.
  • Biocompatibility: The product's biocompatibility makes it suitable for use in biological applications, including drug delivery systems. This property allows for safe interactions with biological tissues, enhancing the efficacy of therapeutic agents.
  • Research Applications: In research, this compound is often explored for its role in studying membrane dynamics and the interactions of lipids with proteins, contributing to our understanding of cellular functions.
  • Potential in Gene Delivery: Recent studies have shown that cationic lipids like hexadecyl 2-(trimethylammonio)ethyl phosphate can facilitate the delivery of genetic material into cells. This potential makes it interesting for developments in gene therapy and molecular biology.

In summary, hexadecyl 2-(trimethylammonio)ethyl phosphate is not just a complex chemical entity but a compound with substantial implications in various fields, especially in biochemistry and material science. Its unique properties allow it to bridge the gap between simple surfactants and advanced biological applications. As a student or scientist, understanding the multifaceted roles of such compounds can lead to innovative solutions in research and industry.

Synonyms
Miltefosine
58066-85-6
Hexadecylphosphocholine
Miltex
Impavido
HDPC
Hexadecylphosphorylcholine
Miltefosina
Miltefosinum
n-Hexadecylphosphorylcholine
n-hexadecylphosphocholine
1-Hexadecylphosphorylcholine
Miltefos
hexadecyl 2-(trimethylazaniumyl)ethyl phosphate
miltefosin
D-18506
hexadecyl 2-(trimethylammonio)ethyl phosphate
Miltefosin C
Fos-choline 16
Miltefosinum [INN-Latin]
Miltefosina [INN-Spanish]
hexadecyl (2-(trimethylAmmonio)ethyl) phosphate
monohexadecylphosphocholine
D 18506
monohexadecylphosphorylcholine
UNII-53EY29W7EC
NSC605583
Miltefosine (INN)
NSC-605583
NSC-758968
BRN 3690495
53EY29W7EC
DTXSID7045942
CHEBI:75283
D18506
MFCD00133396
CHEMBL125
NSC 605583
HePC;Hexadecyl phosphocholine
2-(((Hexadecyloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethylethanaminium hydroxide, inner salt
Choline phosphate, hexadecyl ester, hydroxide, inner salt
DTXCID5025942
4-04-00-01460 (Beilstein Handbook Reference)
MMV688990
Ethanaminium, 2-(((hexadecyloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethyl-, hydroxide, inner salt
NCGC00095169-01
MILTEFOSINE [INN]
Miltefosinum (INN-Latin)
Miltefosina (INN-Spanish)
MILTEFOSINE (MART.)
MILTEFOSINE [MART.]
C21H46NO4P
Miltefosine [INN:BAN]
CAS-58066-85-6
Choline hexadecyl phosphate
Miltefosine?
Miltextrade mark
Miltefosine API
HePC Hydrate
Impavidotrade mark
Impavido (TN)
Choline, inner salt
TF-002
Ethanaminium, 2-(((hexadecyloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethyl-, hydroxide, innner salt
Choline hydroxide, hexadecyl hydrogen phosphate, inner salt
MILTEFOSINE [MI]
Hexadecyl Phosphorylcholine
SCHEMBL26215
MILTEFOSINE [WHO-DD]
SPECTRUM1505329
Miltefosine (Impavido; HePC)
choline phosphate hexadecyl ester, hydroxide, inner salt
GTPL11355
MILTEFOSINE [ORANGE BOOK]
P01CX04
Miltefosine;Hexadecylphosphocholine
Hexadecyl Phosphorylcholine Hydrate
HMS1922D16
HMS2089J15
HMS3649I09
Pharmakon1600-01505329
hexadecylphosphocholine, miltefosine
BCP04506
miltefosine (hexadecylphosphocholine)
Tox21_111466
BDBM50034220
CCG-35584
CCG-36097
CCG-40025
DL-131
HB0412
Hexadecyl 2-(trimethyl-.lambda.~5~-azanyl)ethyl hydrogen phosphate
NSC758968
s3056
1-N-HEXADECYLPHOSPHORYLCHOLINE
AKOS015914886
Tox21_111466_1
BCP9000927
DB09031
FH10347
NCGC00095169-02
NCGC00095169-03
NCGC00095169-05
NCGC00095169-07
HY-13685
BCP0726000071
M2445
NS00004313
hexadecyloxy-2-trimethylammonioethylphosphorate
D02494
AB00642217-03
AB00642217_04
EN300-7397728
Miltefosine, >=98% (perchloric acid titration)
Hexadecyl 2-(N,N,N-trimethylamino)ethyl Phosphate
Q411787
Hexadecyl 2-(Trimethylammonio)ethyl Phosphate Hydrate
2-[hexadecoxy(hydroxy)phosphoryl]oxyethyl-trimethyl-ammonium
Phosphoric Acid Hexadecyl 2-(Trimethylammonio)ethyl Ester
[2-(Hexadecyloxy-hydroxy-phosphoryloxy)-ethyl]-trimethyl-ammonium
3, 4-hydroxy-N,N,N-trimethyl-, hydroxide, inner salt, 4-oxide
hexadecyl 2-(trimethyl-lambda~5~-azanyl)ethyl hydrogen phosphate
Phosphoric Acid Hexadecyl 2-(Trimethylammonio)ethyl Ester Hydrate
2-(((Hexadecycloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethylethanaminium Inner Salt
2-(((Hexadecyloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethylethanaminium hydroxide