O-PHOSPHORYLETHANOLAMINE

O-PHOSPHORYLETHANOLAMINE Basic information
Product Name:O-PHOSPHORYLETHANOLAMINE
Synonyms:ETHANOLAMINE PHOSPHATE;2-HYDROXYETHYLAMMONIUM DIHYDROGEN PHOSPHATE;2-HYDROXYETHYLAMINE ACID PHOSPHATE;2-AMINOETHANOL DIHYDROGEN PHOSPHATE;2-AMINOETHYL DIHYDROGEN PHOSPHATE;O-PHOSPHOETHANOLAMINE;O-PHOSPHORYLETHANOLAMINE;O-PHOSPHOCOLAMINE
CAS:1071-23-4
MF:C2H8NO4P
MW:141.06
EINECS:213-988-5
Product Categories:Pharmaceutical Intermediates
Mol File:1071-23-4.mol
O-PHOSPHORYLETHANOLAMINE Structure
O-PHOSPHORYLETHANOLAMINE Chemical Properties
Melting point 241-243 °C(lit.)
Boiling point 335.8±44.0 °C(Predicted)
density 1.554±0.06 g/cm3(Predicted)
storage temp. Store below +30°C.
Water Solubility Soluble in water
solubility PBS (pH 7.2): 10 mg/ml
pkapK1:5.838(+1);pK2:10.638(0) (25°C)
form powder to crystal
color White to Light yellow
BRN 1758916
InChIKeySUHOOTKUPISOBE-UHFFFAOYSA-N
CAS DataBase Reference1071-23-4(CAS DataBase Reference)
EPA Substance Registry SystemEthanol, 2-amino-, dihydrogen phosphate (ester) (1071-23-4)
Safety Information
Hazard Codes T,C
Risk Statements 25-34
Safety Statements 26-36/37/39-45-27
RIDADR UN 3261 8/PG 2
WGK Germany 3
RTECS KJ5830000
HazardClass 8
PackingGroup III
HS Code 29221990
ToxicityLD50 orally in Rabbit: 5820 mg/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
O-PHOSPHORYLETHANOLAMINE Usage And Synthesis
Chemical PropertiesO-PHOSPHORYLETHANOLAMINE is white powder
UsesO-PHOSPHORYLETHANOLAMINEe is used in the synthesis of Sphingomyelin, a type of sphingolipid found in animal cell membrane.
UsesO-Phosphorylethanolamine has been used:
  • in LHC-8 medium as a supplement in culturing the transformed human liver epithelial (THLE)-2 and THLE-3 cells
  • in C-reactive protein (CRP) binding sucrose flotation experiment
  • to incubate phosphomonoesters with anion-exchange chromatography (AEC) fractions for the detection of phosphatase activity
  • to add in the washed beads for the preparation of phosphorylethanolamine (Pet) -conjugated sepharose column for chromatographic purification of mutant CRP

DefinitionChEBI: The ethanolamine mono-ester of phosphoric acid, and a metabolite of phospholipid metabolism. This phosphomonoester shows strong structural similarity to the inhibitory neurotransmitter GABA, and is decreased in post-mortem Alzheimer's disease brain.
Biochem/physiol ActionsPhosphorylethanolamine participates in phospholipid metabolism. Its release can be stimulated occasionally by depolarizing stimuli. Reduction of phosphorylethanolamine levels has been observed in Alzheimer′s and Huntington′s disease.
Purification MethodsPurification by recrystallisation from aqueous EtOH gives a hydrate (m 140-141o). Its solubility in H2O is 17% and 0.003% in MeOH or EtOH at 22o. [F.lisch & .sterberg J Biol Chem 234 2298 1959, Baer & Staucer Can J Chem 34 434 1956, Christensen J Biol Chem 135 399 1940.] It is a potent inhibitor of ornithine decarboxylase [Gilad & Gilad Biochem Biophys Res Commun 122 277 1984]. [Beilstein 4 IV 1415.]
O-PHOSPHORYLETHANOLAMINE Preparation Products And Raw materials
Citicoline sodium 1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHORYLETHANOLAMINE 1-MYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE O-PHOSPHORYLETHANOLAMINE L-ALPHA-PHOSPHATIDYLCHOLINE, DISTEAROYL ADENOSINE-2':3'-CYCLIC MONOPHOSPHATE, SODIUM SALT 1,2-DILAUROYL-SN-GLYCERO-3-PHOSPHORYLETHANOLAMINE 1,3-DIPALMITOYL-GLYCERO-2-PHOSPHOETHANOLAMINE Calcium phosphorylcholine chloride ADENOSINE 2' -& 3'-MONOPHOSPHATE FREE 1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE BETA-NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE SODIUM SALT DL-O-Phosphoserine NADPH, Tetrasodium Salt 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine CYTIDINE 2'-MONOPHOSPHATE 1-PALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE 1,2-DISTEAROYL-SN-GLYCERO-3-PHOSPHORYLETHANOLAMINE

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