Choline
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Choline
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CAS No:
62-49-7
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Formula:
C5H14NO
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Chemical Name:
Choline
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Synonyms:
Ethanaminium,2-hydroxy-N,N,N-trimethyl-;Choline;2-Hydroxy-N,N,N-trimethylethanaminium;Bilineurine;(2-Hydroxyethyl)trimethylammonium;Choline ion;Choline cation;Nanoveson C;Vitamin J;139741-81-4;2087491-45-8
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CAS No:
Description
Viscous, alkaline liquid. Soluble in water and alcohol. Amounts are expressed in milligrams of choline.
Solid
Choline is a choline that is the parent compound of the cholines class, consisting of ethanolamine having three methyl substituents attached to the amino function. It has a role as a neurotransmitter, a nutrient, a human metabolite, a plant metabolite, a Daphnia magna metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite and an allergen.|A basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism.|Vitamin B refers to several water soluble vitamins often found together in foods, all of which are necessary for normal growth and metabolism, but none of which are synthesized in adequate amounts by humans. The common forms of vitamin B include vitamin B1 (thiamine), B2 (riboflavin), B3 (niacin), B6 (pyridoxine) and B12 (cyanocobalamin). Except for niacin (when given in high doses), there is no evidence that the other B vitamins, in physiologic or even super-physiologic high doses cause liver injury or jaundice. The major forms of vitamin B and selected other water soluble vitamins (biotin, pantothenic acid, choline) are discussed briefly in this record.
Characteristics
20.2
-3.70
Solid
1.09 g/mL at 20 °C
232-233 °C (decomp)
155-230 °C
n20/D 1.418
H2O: soluble
2-8°C
117.8 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|119 Ų [M]+ [CCS Type: DT, Method: stepped-field]|117 Ų [M]+ [CCS Type: TW, Method: calibrated with polyalanine]|117.6 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|118.7 Ų [M*]+
Safety Information
II
8
UN 3286 3/PG 2
1
34
26-36/37/39-45
C
|Danger|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 44 companies from 4 notifications to the ECHA C&L Inventory.
Drug Information
For nutritional supplementation, also for treating dietary shortage or imbalance
Vitamin B refers to several water soluble vitamins often found together in foods, all of which are necessary for normal growth and metabolism, but none of which are synthesized in adequate amounts by humans. The common forms of vitamin B include vitamin B1 (thiamine), B2 (riboflavin), B3 (niacin), B6 (pyridoxine) and B12 (cyanocobalamin). Except for niacin (when given in high doses), there is no evidence that the other B vitamins, in physiologic or even super-physiologic high doses cause liver injury or jaundice. The major forms of vitamin B and selected other water soluble vitamins (biotin, pantothenic acid, choline) are discussed briefly in this record.
Vitamins
This compound is needed for good nerve conduction throughout the CNS (central nervous system) as it is a precursor to acetylcholine (ACh). Choline is also needed for gallbladder regulation, liver function and lecithin (a key lipid) formation. Choline also aids in fat and cholesterol metabolism and prevents excessive fat build up in the liver. Choline has been used to mitigate the effects of Parkinsonism and tardive dyskinesia. Choline deficiencies may result in excessive build-up of fat in the liver, high blood pressure, gastric ulcers, kidney and liver dysfunction and stunted growth.
Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)|Endogenous factors or drugs that increase the transport and metabolism of LIPIDS including the synthesis of LIPOPROTEINS by the LIVER and their uptake by extrahepatic tissues. (See all compounds classified as Lipotropic Agents.)
Choline has known human metabolites that include Trimethylazanium and acetaldehyde.
Choline is a major part of the polar head group of phosphatidylcholine. Phosphatidylcholine's role in the maintenance of cell membrane integrity is vital to all of the basic biological processes: information flow, intracellular communication and bioenergetics. Inadequate choline intake would negatively affect all these processes. Choline is also a major part of another membrane phospholipid, sphingomyelin, also important for the maintenance of cell structure and function. It is noteworthy and not surprising that choline deficiency in cell culture causes apoptosis or programmed cell death. This appears to be due to abnormalities in cell membrane phosphatidylcholine content and an increase in ceramide, a precursor, as well as a metabolite, of sphingomyelin. Ceramide accumulation, which is caused by choline deficiency, appears to activate Caspase, a type of enzyme that mediates apoptosis. Betaine or trimethylglycine is derived from choline via an oxidation reaction. Betaine is one of the factors that maintains low levels of homocysteine by resynthesizing L-methionine from homocysteine. Elevated homocysteine levels are a significant risk factor for atherosclerosis, as well as other cardiovascular and neurological disorders. Acetylcholine is one of the major neurotransmitters and requires choline for its synthesis. Adequate acetylcholine levels in the brain are believed to be protective against certain types of dementia, including Alzheimer's disease.
2-Hydroxy-N,N,N-trimethylethanaminium
Choline Use and Manufacturing
Choline is a substance grouped as a member of the vitamin b complex, although not a vitamin by definition. it is water soluble and is important in nerve function and fat metabolism. it occurs in egg yolk, beef liver, and grains.
Ethanaminium, 2-hydroxy-N,N,N-trimethyl-: ACTIVE
Computed Properties
Molecular Weight:104.17
XLogP3:-0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:104.107539070
Monoisotopic Mass:104.107539070
Topological Polar Surface Area:20.2
Heavy Atom Count:7
Formal Charge:1
Complexity:46.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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