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28319-77-9
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???(??):
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Choline glycerophosphate
???(??):
Alpha GPC;GPC;CHOLINE ALFOSCERATE;glycerophosphocholine;SN-GLYCERO-3-PHOSPHOCHOLINE;GLYCEROPHOSPHORYLCHOLINE;L-ALPHA-GLYCERYLPHOSPHORYLCHOLINE;Alpha GPC powder;L-α-glycerylphosphorylcholine;L-A-glycerophosphorylcholine
CBNumber:
CB5309777
???:
C8H20NO6P
??? ??:
257.22
MOL ??:
28319-77-9.mol

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142.5-143°
??
D25 -2.7° (c = 2.7 in water, pH 2.5); D25 -2.8° (c = 2.6 in water, pH 5.8)
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480℃[at 101 325 Pa]
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0Pa at 25℃
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11 °C
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-20°C
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DMSO(?? ??, ??? ??), ???(?? ???), ?(?? ???)
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soybean
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1000g/L at 25℃
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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-/s3
InChIKey
SUHOQUVVVLNYQR-SBYBRXNCNA-N
SMILES
P([O-])(=O)(OCC[N+](C)(C)C)OC[C@H](O)CO |&1:12,r|
LogP
-5.15 at 25℃
CAS ??????
28319-77-9(CAS DataBase Reference)
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  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? F,T
?? ???? ?? 11-23/24/25-39/23/24/25
????? 16-36/37-45-24/25
????(UN No.) UN 1230 3/PG 2
WGK ?? 2
RTECS ?? KH2775000
HS ?? 29239000
???? ?? KE-05955
????(GHS): GHS hazard pictograms
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 ?? ???? ??? ? ?? ?? ???? ?? - 1? ??;???? ?? ?? 3 ?? GHS hazard pictograms
H412 ??? ??? ?? ????? ??? ?? ????? ?? - ?? ?? 3 P273, P501
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P261 ??·?·??·???·??·...·????? ??? ????.
P273 ???? ???? ???.
P305+P351+P338 ?? ??? ? ?? ?? ???? ????. ???? ?????? ?????. ?? ????.

????????? MSDS


Choline glycerophosphate

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Choline alfoscerate is a nootropic reportedly effective in the treatment of age-associated memory impairment. In man, it decreased and prevented scopolamine-induced amnesia. In vitro studies suggest that choline alfoscerate acts indirectly on cholinergic transmission by elevating the synthesis of acetylcholine.

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Choline glycerophosphate (GPC) is a white waxy solid that is miscible with water, soluble in methanol and ethanol, and insoluble in chloroform, ether, oil, etc. It has no characteristic absorption under UV visible light. The methods for determining GPC content include high-performance liquid chromatography (equipped with an evaporative light scattering detector or refractive index differential detector) and the digestion phosphorus determination method.

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sn-Glycero-3-phosphocholine (Choline Alfoscerate) is a phospholipid; precursor in choline biosynthesis. sn-Glycero-3-phosphocholine is an intermediate in catabolic pathway of phosphatidylcholine. sn-Glycero-3-phosphocholine is used as an Nootropic.

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ChEBI: Choline alfoscerate is a member of the class of phosphocholines that is the choline ester of sn-glycero-3-phosphate. It is one of the major osmolyte in the renal medullary cells. It has a role as a parasympatholytic, a neuroprotective agent, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a member of sn-glycerol 3-phosphates and a member of phosphocholines.

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L-α-Glycerophosphorylcholine is a phospholipid, which is a derivative of phosphatidylcholine.

Synthesis

10 g of phosphorylcholine chloride (1 equivalent, 228 mmol) was dissolved in 200 ml of methanol in a 500 ml three-necked round bottom flask equipped with a thermometer, a reflux condenser and a stirrer. Then, 5.1 g of potassium hydroxide (2 equivalents, 455 mmol) Lt; / RTI & gt; stirred for 1 hour. After warming the reaction to 65 ° C, 10 g of (R) -3-chloro-1,2-propanediol (2 eq, 452 mmol) was added slowly and refluxed for 16 hours to carry out the substitution reaction. After completion of the reaction, 10 ml of water was added to the concentrate obtained by concentration under reduced pressure, and the reaction product was diluted with acetone twice. The aqueous layer was concentrated under reduced pressure to obtain 11.60 g of L-α-glycerophosphorylcholine (sn-Glycero-3-phosphocholine; yield: 99%).

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