(2R)-3-chloro-1,2-propanediol
phosphorylcholine chloride
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
Stage #1: phosphorylcholine chloride With potassium hydroxide In methanol for 1h; Stage #2: (2R)-3-chloro-1,2-propanediol In methanol at 65℃; for 16h; Temperature; | 99% |
Stage #1: phosphorylcholine chloride With potassium hydroxide In ethanol for 0.5h; Stage #2: (2R)-3-chloro-1,2-propanediol In ethanol at 75 - 85℃; for 6h; | 79.6% |
Conditions | Yield |
---|---|
In ethanol at 20℃; for 5h; | 92.11% |
(R)-1,2-diacetoxy glycerylphosphoryl choline
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; for 0.0833333h; | 91% |
(2R)-3-chloro-1,2-propanediol
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
at 60 - 65℃; for 48h; Temperature; | 78.6% |
(2R)-3-chloro-1,2-propanediol
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
at 80 - 85℃; for 50h; | 77.8% |
In ethanol Reflux; | 7.8 g |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
With 717 type ion exchange resin In ethanol; water at 0℃; for 4h; | 77% |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
In methanol; water Solvent; Reflux; | 72.3% |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
Stage #1: (R)-4-bromomethyl-2-methyl-2-ethyl-1,3-dioxolane With sodium hydroxide In isopropyl alcohol at 82℃; for 30h; Stage #2: With sulfuric acid In ethanol; water; isopropyl alcohol | 67.9% |
phosphorylcholine chloride
(R)-oxiranemethanol
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
In ethanol at 75 - 85℃; for 12h; | 67.5% |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
Stage #1: C9H15IO2 With potassium hydroxide In ethanol at 85℃; for 15h; Stage #2: With hydrogenchloride In methanol; ethanol; water | 66.5% |
(R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
Stage #1: (R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane With potassium carbonate In methanol at 65℃; for 18h; Stage #2: phosphorylcholine chloride potassium salt With hydrogenchloride In methanol; water | 65.1% |
all cis-5,8,11,14,17-eicosapentaenoic acid
L-dipalmitoylphosphatidylcholine
A
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
With Rhizomucor miehei lipase Product distribution; Substitution; hydrolysis; Enzymatic reaction; |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
With water at 20 - 25℃; Behandlung des Reaktionsprodukts mit BaCO3; |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
With water; potassium carbonate for 5h; Reflux; | 0.13 g |
Conditions | Yield |
---|---|
Stage #1: siladenoserinol A With sodium hydroxide In methanol for 2h; Reflux; Stage #2: With hydrogenchloride In water |
phosphorylcholine chloride, calcium salt
(R)-oxiranemethanol
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
Stage #1: phosphorylcholine chloride, calcium salt With sodium carbonate In water at 20℃; for 1h; Stage #2: (R)-oxiranemethanol Reagent/catalyst; Concentration; Reflux; | 289 g |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; for 5h; pH=1 - 2; | 45.2 g |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; for 5h; pH=1 - 2; | 45.3 g |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: oxygen / dichloromethane / 20 °C 2: ethanol / 8 h / 0 °C / Reflux 3: 717 type ion exchange resin / ethanol; water / 4 h / 0 °C View Scheme |
L-glycero-3-phosphorylcholine
n-hexadecanoyl chloride
1-palmitoyl-sn-glycero-3-phosphocholine
Conditions | Yield |
---|---|
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol for 1h; Heating; Stage #2: n-hexadecanoyl chloride With TEA In isopropyl alcohol at 25℃; for 0.25h; Further stages.; | 97% |
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol for 1h; Reflux; Stage #2: n-hexadecanoyl chloride With triethylamine at 20℃; for 1h; | 90% |
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol for 1h; Heating; Stage #2: n-hexadecanoyl chloride With TEA In isopropyl alcohol at 25℃; for 0.25h; Further stages.; | 80% |
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol for 1h; Reflux; Stage #2: n-hexadecanoyl chloride With triethylamine In isopropyl alcohol at 25℃; for 0.25h; | 80% |
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol at 100℃; for 1h; Stage #2: n-hexadecanoyl chloride With triethylamine In isopropyl alcohol at 20℃; | 31% |
L-glycero-3-phosphorylcholine
Stearoyl chloride
1-stearoyl-sn-glycero-3-phosphocholine
Conditions | Yield |
---|---|
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol for 1h; Heating; Stage #2: Stearoyl chloride With TEA In isopropyl alcohol at 20℃; for 0.583333h; Further stages.; | 97% |
With di(n-butyl)tin oxide; triethylamine | 70% |
(Z)-9-octadecenoyl chloride
L-glycero-3-phosphorylcholine
1-oleoyl-L-lysophosphatidylcholine
Conditions | Yield |
---|---|
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol for 1h; Heating; Stage #2: (Z)-9-octadecenoyl chloride With TEA In isopropyl alcohol at 20℃; for 0.583333h; Further stages.; | 97% |
Conditions | Yield |
---|---|
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol for 1h; Heating; Stage #2: n-dodecanoyl chloride With TEA In isopropyl alcohol at 20℃; for 0.583333h; Further stages.; | 97% |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
In methanol; water at 0℃; for 4h; | 91% |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
In methanol; water | 91% |
cis-Octadecenoic acid
L-glycero-3-phosphorylcholine
dioleoylphosphatidylcholine
Conditions | Yield |
---|---|
With dmap; Hyflo Super-Cel; dicyclohexyl-carbodiimide In chloroform at 30℃; | 90.3% |
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 12h; Reagent/catalyst; Solvent; Darkness; | 82.33% |
triisopropylsilyl trifluoromethanesulfonate
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere; regioselective reaction; | 87% |
L-glycero-3-phosphorylcholine
Stearoyl chloride
1-stearoyl-2-lyso-sn-glycero-3-phosphocholine
Conditions | Yield |
---|---|
Stage #1: L-glycero-3-phosphorylcholine; Stearoyl chloride With di(n-butyl)tin oxide In ethanol for 0.5h; Reflux; Stage #2: Stearoyl chloride With triethylamine In tetrahydrofuran at 50℃; for 3h; | 83.3% |
L-glycero-3-phosphorylcholine
2-[[[(carboxymethyl)oxy]hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium
Conditions | Yield |
---|---|
With ruthenium trichloride; sodium periodate; water In acetonitrile at 0℃; | 82% |
With ruthenium trichloride; sodium periodate In water at 20℃; for 2h; Product distribution / selectivity; Cooling in ice-water bath; |
Conditions | Yield |
---|---|
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol for 1h; Heating; Stage #2: butyryl chloride With dmap In isopropyl alcohol at 25℃; for 48h; Further stages.; | 82% |
L-glycero-3-phosphorylcholine
1-hexadecylcarboxylic acid
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With dmap; Hyflo Supre-Cel; dicyclohexyl-carbodiimide In chloroform at 30℃; | 80% |
Stage #1: L-glycero-3-phosphorylcholine; 1-hexadecylcarboxylic acid With dmap In dichloromethane for 0.333333h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane for 8h; | 80.3% |
Stage #1: 1-hexadecylcarboxylic acid With 1,1'-carbonyldiimidazole In chloroform-d1 at 20℃; for 0.75h; Condensation; Stage #2: L-glycero-3-phosphorylcholine With 1,8-diazabicyclo[5.4.0]undec-7-ene In chloroform-d1 at 20℃; for 24h; Acylation; |
Conditions | Yield |
---|---|
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol for 1h; Heating; Stage #2: n-valeryl chloride With dmap In isopropyl alcohol at 25℃; for 48h; Further stages.; | 80% |
3-(tritylthio) propanoic acid
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
Stage #1: 3-(tritylthio) propanoic acid With 1,1'-carbonyldiimidazole In dimethyl sulfoxide for 2h; Stage #2: L-glycero-3-phosphorylcholine With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 20℃; | 80% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole In dimethyl sulfoxide at 20℃; for 6h; Time; |
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In chloroform for 20h; | 77% |
L-glycero-3-phosphorylcholine
Hexanoyl chloride
L-alpha-caproyl lysophosphatidylcholine
Conditions | Yield |
---|---|
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol for 1h; Heating; Stage #2: Hexanoyl chloride With dmap In isopropyl alcohol at 25℃; for 48h; Further stages.; | 75% |
L-glycero-3-phosphorylcholine
6-((1,1-dimethylethyl)diphenylsilyloxy)hexanoic acid
Conditions | Yield |
---|---|
Stage #1: 6-((1,1-dimethylethyl)diphenylsilyloxy)hexanoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 35℃; for 4h; Stage #2: L-glycero-3-phosphorylcholine With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; dimethyl sulfoxide at 20 - 40℃; for 20h; | 71% |
tetradecylthioacetic Acid
L-glycero-3-phosphorylcholine
1,2-di-[2-(tetradecylthio)acetyl]-sn-glycero-3-phosphocholine
Conditions | Yield |
---|---|
Stage #1: tetradecylthioacetic Acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 2.75h; Inert atmosphere; Stage #2: L-glycero-3-phosphorylcholine With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; dimethyl sulfoxide at 20℃; for 16h; Inert atmosphere; | 70% |
L-glycero-3-phosphorylcholine
3-O-acetylbetulinic acid chloride
Conditions | Yield |
---|---|
Stage #1: L-glycero-3-phosphorylcholine With di(n-butyl)tin oxide In isopropyl alcohol for 1h; Reflux; Stage #2: 3-O-acetylbetulinic acid chloride With triethylamine In isopropyl alcohol at 20℃; for 5h; | 69% |
L-glycero-3-phosphorylcholine
trityl chloride
1-O-trityl-sn-glycero-3-phosphocholine
Conditions | Yield |
---|---|
With zinc(II) chloride In N,N-dimethyl-formamide at 5℃; for 10h; | 67% |
With zinc(II) chloride In N,N-dimethyl-formamide at 5℃; | 51.2% |
Stage #1: L-glycero-3-phosphorylcholine With zinc(II) chloride In N,N-dimethyl-formamide at 4℃; for 0.5h; Stage #2: trityl chloride In N,N-dimethyl-formamide at 4℃; | 50% |
1.Introduction of Choline glycerophosphate
The CAS register number of Choline glycerophosphate is 28319-77-9. It also can be called as 2-(((2,3-Dihydroxypropoxy)hydroxyphosphinyl)oxy)-N,N,N-trimethylethanaminium inner salt and the IUPAC name about this chemical is [(2R)-2,3-dihydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate. The molecular formula about this chemical is C8H20NO6P and the molecular weight is 257.22. It belongs to the following product categories, such as Activity Other; Activity; Enzyme Substrates and so on. This chemical can be used as a putative cognition enhancer and a putative growth hormone secretagogue.
2.Physical properties of Choline glycerophosphate
(1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 7; (6)#H bond donors: 3; (7)#Freely Rotating Bonds: 10; (8)Polar Surface Area: 86.86Å2.
3.Structure descriptors of Choline glycerophosphate
(1)SMILES: [O-]P(=O)(OC[C@H](O)CO)OCC[N+](C)(C)C
(2)InChI: InChI=1/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/t8-/m1/s1
(3)InChIKey: SUHOQUVVVLNYQR-MRVPVSSYBR
(4)Std. InChI: InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/t8-/m1/s1
(5)Std. InChIKey: SUHOQUVVVLNYQR-MRVPVSSYSA-N
4.Safety information of Choline glycerophosphate
This chemical is toxic by inhalation, in contact with skin and if swallowed, it is danger of very serious irreversible effects and it is highly flammable. When you are using it, wear suitable protective clothing and gloves, you need keep away from sources of ignition. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
5.The toxicity data of Choline glycerophosphate
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | > 650mg/kg (650mg/kg) | Japanese Kokai Tokyo Koho Patents. Vol. #93-32553, | |
mouse | LD50 | oral | > 13gm/kg (13000mg/kg) | Japanese Kokai Tokyo Koho Patents. Vol. #93-32553, |
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