EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

laevo-alpha-glyceryl phosphoryl choline
L-alpha-glycerylphosphorylcholine

Supplier Sponsors

CAS Number: 28319-77-9Picture of molecule3D/inchi
Other(deleted CASRN):103709-68-8
ECHA EINECS - REACH Pre-Reg:248-962-2
FDA UNII: 60M22SGW66
Beilstein Number:6062450
MDL:MFCD00063544
XlogP3-AA:-2.30 (est)
Molecular Weight:257.22336200
Formula:C8 H20 N O6 P
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:cosmetic ingredient for skin conditioning
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 FDA/DG SANTE Petitions, Reviews, Notices:
GRN 419 L-alpha-glycerylphosphorylcholine View - notice PDF
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 142.50 °C. @ 760.00 mm Hg
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w): -5.398 (est)
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
AIDP
Alpha GPC Glycerylphosphorylcholine 50%
BOC Sciences
For experimental / research use only.
sn-Glycero-3-phosphocholine >98%
Odor: characteristic
Use: 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.
Indis NV
For experimental / research use only.
Glyceryl Phosphoryl Choline
Jiangyin Healthway
Alpha GPC
New functional food ingredients
Santa Cruz Biotechnology
For experimental / research use only.
sn-Glycero-3-phosphocholine
Sigma-Aldrich: Sigma
For experimental / research use only.
sn-Glycero-?3-?phosphocholine inner salt from egg yolk, 5 mg/mL in methanol, ∼98%
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50 > 13000 mg/kg
Japanese Kokai Tokyo Koho Patents. Vol. #93-32553

intravenous-mouse LD50 > 650 mg/kg
Japanese Kokai Tokyo Koho Patents. Vol. #93-32553

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
cosmetic ingredient for skin conditioning
Recommendation for laevo-alpha-glyceryl phosphoryl choline usage levels up to:
 not for fragrance use.
 
Recommendation for laevo-alpha-glyceryl phosphoryl choline flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Dietary Reference Values for choline
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :657272
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
[(2R)-2,3-dihydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
Chemidplus:0028319779
 
References:
 [(2R)-2,3-dihydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):657272
Pubchem (sid):135030234
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C00670
HMDB (The Human Metabolome Database):HMDB00086
FooDB:FDB021802
YMDB (Yeast Metabolome Database):YMDB00309
FDA Listing of Food Additive Status:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 alpha-GPC
 choline alfoscerate
[(2R)-2,3-dihydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
L-alpha-glycerophosphocholine
L-alpha-glycerophosphorylcholine
L-alpha-glyceryl phosphoryl choline
L-alpha-glycerylphosphorylcholine
laevo-alpha-glycerylphosphorylcholine
 

Articles:

PubMed:Excessive alcohol consumption induces methane production in humans and rats.
PubMed:[Detection of effective treatment of amnestic mild cognitive impairement with cereton by testing of lipids markers].
PubMed:Unexpected effects of acetylcholine precursors on pilocarpine seizure-induced neuronal death.
PubMed:[A comparative chemoreactome analysis of mexidol].
PubMed:[Combined therapy of cerebrovascular disorders with neuroprotectors].
PubMed:Targeting Mitochondrial Dysfunction with L-Alpha Glycerylphosphorylcholine.
PubMed:Late treatment with choline alfoscerate (l-alpha glycerylphosphorylcholine, α-GPC) increases hippocampal neurogenesis and provides protection against seizure-induced neuronal death and cognitive impairment.
PubMed:l-Alpha Glycerylphosphorylcholine as a Potential Radioprotective Agent in Zebrafish Embryo Model.
PubMed:[Analysis of choline alfoscerate effectiveness in chronic ocular ischemic syndrome].
PubMed:[Pathogenetic approaches to treatment of cognitive disorders in patients with diabetes mellitus].
PubMed:Phospholipase A1-catalyzed hydrolysis of soy phosphatidylcholine to prepare l-α-glycerylphosphorylcholine in organic-aqueous media.
PubMed:Direct targeted quantitative molecular imaging of neurotransmitters in brain tissue sections.
PubMed:Radio-neuroprotective effect of L-alpha-glycerylphosphorylcholine (GPC) in an experimental rat model.
PubMed:Protective effects of L-alpha-glycerylphosphorylcholine on ischaemia-reperfusion-induced inflammatory reactions.
PubMed:L-α-glycerylphosphorylcholine reduces the microcirculatory dysfunction and nicotinamide adenine dinucleotide phosphate-oxidase type 4 induction after partial hepatic ischemia in rats.
PubMed:Peripheral inflammatory activation after hippocampus irradiation in the rat.
PubMed:[The use of choline alfoscerate (gliatiline) in patients with ischemic stroke].
PubMed:[Approaches to the treatment of tympanophonia taking into consideration specific psychological features of the patient].
PubMed:Modulation of monoaminergic transporters by choline-containing phospholipids in rat brain.
PubMed:Methane biogenesis during sodium azide-induced chemical hypoxia in rats.
PubMed:[Influence of neuroprotectors with choline-positive action on the level of brain-injury markers during acute ischemic stroke].
PubMed:[The use of cerepro (choline alfoscerate) in the treatment of outpatients with chronic progressive cerebrovascular disease].
PubMed:Purification of L-alpha glycerylphosphorylcholine by column chromatography.
PubMed:Effects of cholinergic agonists and antagonists under conditions of spleen denervation in rats with endotoxic shock.
PubMed:[Anti-inflammatory role of cholinergic and serotonergic systems in shock].
PubMed:[Efficacy of cereton in the acute period of ischemic stroke].
PubMed:[Use of cholinomimetics in the treatment of endogenous autism in children].
PubMed:L-alpha-glycerylphosphorylcholine inhibits the transfer function of phosphatidylinositol transfer protein alpha.
PubMed:Treatment of dementia with neurotransmission modulation.
PubMed:Cognitive improvement in mild to moderate Alzheimer's dementia after treatment with the acetylcholine precursor choline alfoscerate: a multicenter, double-blind, randomized, placebo-controlled trial.
PubMed:L-alpha-glycerylphosphorylcholine enhances the amplitude of the pattern electroretinogram in rhesus monkeys. A pilot study.
PubMed:Effect of L-alpha glycerylphosphorylcholine on muscarinic receptors and membrane microviscosity of aged rat brain.
PubMed:Long term choline alfoscerate treatment counters age-dependent microanatomical changes in rat brain.
PubMed:Choline acetyltransferase and acetylcholinesterase in the hippocampus of aged rats: sensitivity to choline alphoscerate treatment.
PubMed:Effect of ipsilateral lesioning of the nucleus basalis magnocellularis and of L-alpha-glyceryl phosphorylcholine treatment on choline acetyltransferase and acetylcholinesterase in the rat fronto-parietal cortex.
PubMed:Cholinergic neurotransmission in the hippocampus of aged rats: influence of L-alpha-glycerylphosphorylcholine treatment.
PubMed:Effect of acute and short-term administration of cholinomimetic drugs on corticosterone secretion in the rat.
PubMed:Nerve growth factor receptor immunoreactivity in the cerebellar cortex of aged rats: effect of choline alfoscerate treatment.
PubMed:Absorption, tissue distribution and excretion of radiolabelled compounds in rats after administration of [14C]-L-alpha-glycerylphosphorylcholine.
PubMed:A comparative study of free plasma choline levels following intramuscular administration of L-alpha-glycerylphosphorylcholine and citicoline in normal volunteers.
PubMed:Molecular mechanisms mediating the effects of L-alpha-glycerylphosphorylcholine, a new cognition-enhancing drug, on behavioral and biochemical parameters in young and aged rats.
PubMed:Effect of choline alfoscerate treatment on changes in rat hippocampus mossy fibres induced by monolateral lesioning of the nucleus basalis magnocellularis.
PubMed:L-alpha-glycerylphosphorylcholine antagonizes scopolamine-induced amnesia and enhances hippocampal cholinergic transmission in the rat.
PubMed:Behavioral effects of L-alpha-glycerylphosphorylcholine: influence on cognitive mechanisms in the rat.
PubMed:Oral choline alfoscerate counteracts age-dependent loss of mossy fibres in the rat hippocampus.
PubMed:Age-related structural changes in the rat cerebellar cortex: effect of choline alfoscerate treatment.
PubMed:Age-related anatomical changes in the rat hippocampus: retardation by choline alfoscerate treatment.
PubMed:Effect of L-alpha-glyceryl-phosphorylcholine on amnesia caused by scopolamine.
PubMed:Changes in the interaction between CNS cholinergic and dopaminergic neurons induced by L-alpha-glycerylphosphorylcholine, a cholinomimetic drug.
PubMed:[STUDIES ON THE HYDROLYSIS OF LECITHINE WITH HYDROXIDES OF ALKALINE EARTH METALS AND THE PREPARATION OF L-ALPHA-GLYCERYLPHOSPHORYLCHOLINE].
PubMed:Synthesis of saturated and unsaturated L-alpha-lecithins; acylation of the cadmium chloride compound of L-alpha-glycerylphosphorylcholine.
PubMed:The preparation of lecithin from L-alpha-glycerylphosphorylcholine.
PubMed:An enzymatic route to L-alpha-glycerylphosphorylcholine.
PubMed:The preparation of L-alpha-glycerylphosphorylcholine from lecithins.
PubMed:L-alpha-glycerylphosphorylcholine.
 
Notes:
Glycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also one of the four major organic osmolytes in renal medullary cells, changing their intracellular osmolyte concentration in parallel with extracellular tonicity during cellular osmoadaptation. As an osmolyte, Glycerophosphorylcholine counteracts the effects of urea on enzymes and other macromolecules. Kidneys (especially medullar cells), which are exposed under normal physiological conditions to widely fluctuating extracellular solute concentrations, respond to hypertonic stress by accumulating the organic osmolytes glycerophosphorylcholine (GPC), betaine, myo-inositol, sorbitol and free amino acids. Increased intracellular contents of these osmolytes are achieved by a combination of increased uptake (myo-inositol and betaine) and synthesis (sorbitol, GPC), decreased degradation (GPC) and reduced osmolyte release. [HMDB]
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