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CAS No.: | 58066-85-6 |
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Name: | Miltefosine |
Article Data: | 14 |
Molecular Structure: | |
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 |
Conditions | Yield |
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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% |
2-bromoethyl hexadecyl hydrogen phosphate
trimethylamine
hexadecylphosphocholine
Conditions | Yield |
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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; |
Conditions | Yield |
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In dichloromethane; acetonitrile at 20℃; | 80% |
Conditions | Yield |
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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% |
trimethylamine
hexadecylphosphocholine
Conditions | Yield |
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In chloroform; water; isopropyl alcohol; acetonitrile Yield given; |
2-hexadecyloxy-[1,3,2]dioxaphospholane 2-oxide
trimethylamine
hexadecylphosphocholine
Conditions | Yield |
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In acetonitrile at 70℃; for 12h; |
1-Hexadecanol
hexadecylphosphocholine
Conditions | Yield |
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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 |
Conditions | Yield |
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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 |
2-octyloxy-1,3,2-dioxaphospholane
hexadecylphosphocholine
Conditions | Yield |
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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 |
Conditions | Yield |
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In methanol; ethanol at 50℃; for 72h; | 136 mg |
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
N-Hexadecylphosphorylcholine (CAS NO.58066-85-6) is used to treat breast cancer.
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. |
A poison by ingestion. When heated to decomposition it emits toxic vapors of NOx and POx.
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 .