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28319-77-9

Basic Information
CAS No.: 28319-77-9
Name: Ethanaminium,2-[[[(2R)-2,3-dihydroxypropoxy]hydroxyphosphinyl]oxy]-N,N,N-trimethyl-, innersalt
Molecular Structure:
Molecular Structure of 28319-77-9 (Ethanaminium,2-[[[(2R)-2,3-dihydroxypropoxy]hydroxyphosphinyl]oxy]-N,N,N-trimethyl-, innersalt)
Formula: C8H20NO6P
Molecular Weight: 257.22
Synonyms: Alfoscerate de choline;BRN 6062450;Calcium (glycerophosphate de);Choline alfoscerate;Choline alphoscerate;Cholini alfosceras;Cholini glycerophosphas;Colina glicerofosfato;Glycerophosphate de choline;L-a-Glycerophosphorylcholine (choline alfoscerate) (GPC);L-alpha-Glycerylphosphoryl choline,GPC;Choline glycerophosphate;
EINECS: 248-962-2
Density:
Melting Point: -98oC
Boiling Point:
Flash Point: 11 °C
Solubility:
Appearance: White waxy solid
Hazard Symbols: FlammableF,ToxicT
Risk Codes: 11-23/24/25-39/23/24/25
Safety: 16-36/37-45
Transport Information:
PSA: 108.86000
LogP: -0.38240
Synthetic route
57090-45-6

(2R)-3-chloro-1,2-propanediol

107-73-3

phosphorylcholine chloride

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
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%

(R)-3-glycerylcycloethyl phosphate

75-50-3

trimethylamine

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
In ethanol at 20℃; for 5h;92.11%
54672-38-7

(R)-1,2-diacetoxy glycerylphosphoryl choline

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; for 0.0833333h;91%
57090-45-6

(2R)-3-chloro-1,2-propanediol

phosphorylcholine chloride potassium salt

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
at 60 - 65℃; for 48h; Temperature;78.6%
57090-45-6

(2R)-3-chloro-1,2-propanediol

C5H13NO4P(1-)*Cl(1-)*2Na(1+)

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
at 80 - 85℃; for 50h;77.8%
In ethanol Reflux;7.8 g

C8H21NO6P(1+)*Cl(1-)

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
With 717 type ion exchange resin In ethanol; water at 0℃; for 4h;77%

phosphorylcholine chloride potassium salt

(2S)-3,4-dimethoxybenzylglycidol

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
In methanol; water Solvent; Reflux;72.3%

(R)-4-bromomethyl-2-methyl-2-ethyl-1,3-dioxolane

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
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%
107-73-3

phosphorylcholine chloride

57044-25-4

(R)-oxiranemethanol

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
In ethanol at 75 - 85℃; for 12h;67.5%

C9H15IO2

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
Stage #1: C9H15IO2 With potassium hydroxide In ethanol at 85℃; for 15h;
Stage #2: With hydrogenchloride In methanol; ethanol; water
66.5%

phosphorylcholine chloride potassium salt

57044-24-3

(R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
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%
10417-94-4

all cis-5,8,11,14,17-eicosapentaenoic acid

63-89-8

L-dipalmitoylphosphatidylcholine

A

28319-77-9

L-glycero-3-phosphorylcholine

B

1-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-sn-glycero-3-phosphocholine

C

PC(36:5)

Conditions
ConditionsYield
With Rhizomucor miehei lipase Product distribution; Substitution; hydrolysis; Enzymatic reaction;
(-)(R)-glycerol-1.2-isopropylidene ether-3--sulfate

(-)(R)-glycerol-1.2-isopropylidene ether-3--sulfate

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
With water at 20 - 25℃; Behandlung des Reaktionsprodukts mit BaCO3;

(S)-glycidyl phosphorylcholine

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
With water; potassium carbonate for 5h; Reflux;0.13 g
1417365-52-6

siladenoserinol A

A

1426535-84-3

C31H57NO7

B

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
Stage #1: siladenoserinol A With sodium hydroxide In methanol for 2h; Reflux;
Stage #2: With hydrogenchloride In water
4826-71-5

phosphorylcholine chloride, calcium salt

57044-25-4

(R)-oxiranemethanol

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
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

C10H22NO7P

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; for 5h; pH=1 - 2;45.2 g

C11H24NO7P

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; for 5h; pH=1 - 2;45.3 g

(R)-2-(oxiran-2-ylmethoxy)-1,3,2-dioxaphospholane

28319-77-9

L-glycero-3-phosphorylcholine

Conditions
ConditionsYield
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
28319-77-9

L-glycero-3-phosphorylcholine

112-67-4

n-hexadecanoyl chloride

17364-16-8, 17364-17-9, 17364-18-0, 14863-27-5

1-palmitoyl-sn-glycero-3-phosphocholine

Conditions
ConditionsYield
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%
28319-77-9

L-glycero-3-phosphorylcholine

112-76-5

Stearoyl chloride

19420-57-6

1-stearoyl-sn-glycero-3-phosphocholine

Conditions
ConditionsYield
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; triethylamine70%
112-77-6

(Z)-9-octadecenoyl chloride

28319-77-9

L-glycero-3-phosphorylcholine

19420-56-5

1-oleoyl-L-lysophosphatidylcholine

Conditions
ConditionsYield
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%
112-16-3

n-dodecanoyl chloride

28319-77-9

L-glycero-3-phosphorylcholine

20559-18-6

LPC (12:0)

Conditions
ConditionsYield
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%

aqueous cadmium chloride

28319-77-9

L-glycero-3-phosphorylcholine

sn-glycero-3-phosphocholine cadmium chloride complex

Conditions
ConditionsYield
In methanol; water at 0℃; for 4h;91%

aqueous cadmium chloride

28319-77-9

L-glycero-3-phosphorylcholine

1-α-glycerophosphocholine cadmium chloride salt

Conditions
ConditionsYield
In methanol; water91%
112-80-1

cis-Octadecenoic acid

28319-77-9

L-glycero-3-phosphorylcholine

4235-95-4

dioleoylphosphatidylcholine

Conditions
ConditionsYield
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%
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

28319-77-9

L-glycero-3-phosphorylcholine

C17H40NO6PSi

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere; regioselective reaction;87%
28319-77-9

L-glycero-3-phosphorylcholine

112-76-5

Stearoyl chloride

19420-57-6

1-stearoyl-2-lyso-sn-glycero-3-phosphocholine

Conditions
ConditionsYield
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%
28319-77-9

L-glycero-3-phosphorylcholine

853798-56-8

2-[[[(carboxymethyl)oxy]hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium

Conditions
ConditionsYield
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;
28319-77-9

L-glycero-3-phosphorylcholine

141-75-3

butyryl chloride

C12H26NO7P

Conditions
ConditionsYield
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%
28319-77-9

L-glycero-3-phosphorylcholine

57-10-3

1-hexadecylcarboxylic acid

63-89-8

L-dipalmitoylphosphatidylcholine

Conditions
ConditionsYield
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;
28319-77-9

L-glycero-3-phosphorylcholine

638-29-9

n-valeryl chloride

C13H28NO7P

Conditions
ConditionsYield
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%
27144-18-9

3-(tritylthio) propanoic acid

28319-77-9

L-glycero-3-phosphorylcholine

bis(tritylmercaptopropionate)glycerophosphorylcholine

Conditions
ConditionsYield
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;
28319-77-9

L-glycero-3-phosphorylcholine

1,2-α-eleostearoyl-sn-glycero-3-phosphocholine

Conditions
ConditionsYield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In chloroform for 20h;77%
28319-77-9

L-glycero-3-phosphorylcholine

142-61-0

Hexanoyl chloride

58445-96-8

L-alpha-caproyl lysophosphatidylcholine

Conditions
ConditionsYield
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%
28319-77-9

L-glycero-3-phosphorylcholine

122846-05-3

6-((1,1-dimethylethyl)diphenylsilyloxy)hexanoic acid

C52H76NO10PSi2

Conditions
ConditionsYield
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%
2921-20-2

tetradecylthioacetic Acid

28319-77-9

L-glycero-3-phosphorylcholine

636589-28-1

1,2-di-[2-(tetradecylthio)acetyl]-sn-glycero-3-phosphocholine

Conditions
ConditionsYield
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%
28319-77-9

L-glycero-3-phosphorylcholine

59868-82-5

3-O-acetylbetulinic acid chloride

1-acetylbetulinyl-Sn-glycero-3-phosphocholine

Conditions
ConditionsYield
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%
28319-77-9

L-glycero-3-phosphorylcholine

76-83-5

trityl chloride

103675-56-5

1-O-trityl-sn-glycero-3-phosphocholine

Conditions
ConditionsYield
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%
Raw Materials
54672-38-7
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Specification

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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