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58066-85-6

Basic Information
CAS No.: 58066-85-6
Name: Miltefosine
Article Data: 14
Molecular Structure:
Molecular Structure of 58066-85-6 (Miltefosine)
Formula: C21H46NO4P
Molecular Weight: 407.574
Synonyms: D 18506;FOS-Choline16;Hexadecylphosphocholine;Hexadecylphosphorylcholine;Miltex;NSC 605583;N-Hexadecylphosphocholine;Ethanaminium,2-[[(hexadecyloxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-, inner salt;
EINECS: 622-572-6
Melting Point: 232-234oC
Appearance: white to off-white solid
Hazard Symbols: Xn
Risk Codes: 22-43
Safety: 36/37
PSA: 68.40000
LogP: 6.74570
Synthetic route
36653-82-4

1-Hexadecanol

2-(((2-cyanoethoxy)(diisopropylamino)phosphaneyl)oxy)-N,N,N-trimethylethan-1-aminium tetraphenylborate

58066-85-6

hexadecylphosphocholine

Conditions
ConditionsYield
Stage #1: 1-Hexadecanol; 2-(((2-cyanoethoxy)(diisopropylamino)phosphaneyl)oxy)-N,N,N-trimethylethan-1-aminium tetraphenylborate With 1H-tetrazole In acetonitrile at 25℃; for 0.5h; Inert atmosphere;
Stage #2: With tert.-butylhydroperoxide In acetonitrile
Stage #3: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 25℃; Reagent/catalyst; Inert atmosphere;
91%
72358-41-9

2-bromoethyl hexadecyl hydrogen phosphate

75-50-3

trimethylamine

58066-85-6

hexadecylphosphocholine

Conditions
ConditionsYield
In chloroform; water; isopropyl alcohol; acetonitrile at 70℃;81%
In dichloromethane; chloroform; water; isopropyl alcohol; acetonitrile for 3h;54%
With toluene at 60℃; Behandeln einer Loesung des Reaktionsprodukts in Methanol mit Silbercarbonat;
In ethanol; chloroform; acetonitrile for 3h; Ambient temperature; Yield given;

hexadecyl methyl 2-bromoethylphosphate

75-50-3

trimethylamine

58066-85-6

hexadecylphosphocholine

Conditions
ConditionsYield
In dichloromethane; acetonitrile at 20℃;80%
36653-82-4

1-Hexadecanol

55357-38-5

choline tosylate

58066-85-6

hexadecylphosphocholine

Conditions
ConditionsYield
Stage #1: 1-Hexadecanol With triethylamine; trichlorophosphate In chloroform at 0 - 20℃;
Stage #2: choline tosylate With pyridine In chloroform at 0 - 20℃;
Stage #3: With water In chloroform at 20℃; for 1h;
17.2%

Phosphorobromidic acid 2-bromo-ethyl ester hexadecyl ester

75-50-3

trimethylamine

58066-85-6

hexadecylphosphocholine

Conditions
ConditionsYield
In chloroform; water; isopropyl alcohol; acetonitrile Yield given;
146556-18-5

2-hexadecyloxy-[1,3,2]dioxaphospholane 2-oxide

75-50-3

trimethylamine

58066-85-6

hexadecylphosphocholine

Conditions
ConditionsYield
In acetonitrile at 70℃; for 12h;
36653-82-4

1-Hexadecanol

58066-85-6

hexadecylphosphocholine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diisopropylamine / tetrahydrofuran / 2 h / 0 - 20 °C
2: acetonitrile / 12 h / 70 °C
View Scheme
Multi-step reaction with 2 steps
1.1: I2 / CH2Cl2
1.2: pyridine / CH2Cl2 / 0.75 h
2.1: 80 percent / CH2Cl2; acetonitrile; various solvent(s) / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: N(C2H5)3 / CHCl3
2: CHCl3; acetonitrile; ethanol / 3 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: tetrachloromethane / und Erhitzen des Reaktionsprodukts mit Wasser
2: toluene / 60 °C / Behandeln einer Loesung des Reaktionsprodukts in Methanol mit Silbercarbonat
View Scheme
Multi-step reaction with 2 steps
1.1: trichlorophosphate; triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
1.2: 0 - 20 °C / Inert atmosphere
1.3: 40 °C
2.1: chloroform; acetonitrile; isopropyl alcohol; water / 70 °C
View Scheme
36653-82-4

1-Hexadecanol

potassium hydroxide

potassium hydroxide

58066-85-6

hexadecylphosphocholine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diisopropylethylamine / CH2Cl2 / 0.67 h / -20 °C
2: Br2 / CH2Cl2 / -20 --> 0 deg C, then 0 deg C, 10 min
3: propan-2-ol; acetonitrile; CHCl3; H2O
View Scheme
216437-33-1

2-octyloxy-1,3,2-dioxaphospholane

58066-85-6

hexadecylphosphocholine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Br2 / CH2Cl2 / -20 --> 0 deg C, then 0 deg C, 10 min
2: propan-2-ol; acetonitrile; CHCl3; H2O
View Scheme

C18H37BrO4P(1-)

75-50-3

trimethylamine

58066-85-6

hexadecylphosphocholine

Conditions
ConditionsYield
In methanol; ethanol at 50℃; for 72h;136 mg
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Chemistry


IUPAC Name: Hexadecyl 2-(trimethylazaniumyl)ethyl phosphate 
Empirical Formula: C21H46NO4P
Molecular Weight: 407.568
Product Categories: Miscellaneous Natural Products 
Appearance: white to off-white powder
Melting Point: 232-234 °C
Classification Code of N-Hexadecylphosphorylcholine (CAS NO.58066-85-6): Anti-Infective Agents; Antifungal Agents; Antineoplastic agents; Antiparasitic Agents; Antiprotozoal agents; Drug / Therapeutic Agent

Uses

 N-Hexadecylphosphorylcholine (CAS NO.58066-85-6) is used to treat breast cancer.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 246mg/kg (246mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Lipids. Vol. 22, Pg. 930, 1987.

Safety Profile

A poison by ingestion. When heated to decomposition it emits toxic vapors of NOx and POx.

Specification

  N-Hexadecylphosphorylcholine (CAS NO.58066-85-6), its Synonyms are 2-(((Hexadecyloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethylethanaminium hydroxide, inner salt ; Miltefosine ; Choline phosphate, hexadecyl ester, hydroxide, inner salt (6CI) ; Hexadecylphosphocholine ; Hexadecylphosphorylcholine ; Miltefosina ; Choline hydroxide, hexadecyl hydrogen phosphate, inner salt ; Ethanaminium, 2-(((hexadecyloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethyl-, hydroxide, inner salt .