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{{BioPsy}}
 
{{BioPsy}}
[[Image:Choline-skeletal.png|thumb|200px|right|Choline]]
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| ImageFile = Choline-skeletal.png
'''Choline''' is a [[nutrient]], essential for [[cardiovascular]] and [[brain]] function, and for [[cellular membrane]] composition and repair.
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| IUPACName =
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| OtherNames =
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| Section1 = {{Chembox Identifiers
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| CASNo = 62-49-7
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| PubChem = 305
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| SMILES =
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| MeSHName = Choline
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}}
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| Section2 = {{Chembox Properties
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| Formula = C5H14NO+
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| MolarMass = 104.171
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| Appearance =
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| Density =
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| MeltingPt =
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| BoilingPt =
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}}
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| Section3 = {{Chembox Hazards
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| Solubility =
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| Autoignition =
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'''Choline''' is an [[organic compound]], classified as an [[essential nutrient]]<ref>{{pauling|id=othernuts/choline/|title=Choline|author=Jane Higdon}}</ref><ref>"[http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/cho_0283.shtml Choline], ''PDRHealth''</ref><ref>"[http://www.abc.net.au/rn/talks/8.30/helthrpt/stories/s119524.htm Choline]" (An interview with Steven Zeisel, Editor-in-Chief of the Journal of Nutritional Biochemistry), ''Radio National Health Report with Norman Swan'', Monday 17 April 2000</ref> and usually grouped within the [[Vitamin B]] complex. This natural [[amine]] is found in the lipids that make up cell membranes and in the [[neurotransmitter]] [[acetylcholine]]. Adequate intakes (AI) for this [[micronutrient]] of between 425 to 550 milligrams daily, for adults, have been established by the Food and Nutrition Board of the [[Institute of Medicine]] of the [[United States National Academy of Sciences|National Academy of Sciences]].
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==History==
 
==History==
Choline was discovered by Andreas Strecker in [[1862]] and [[chemical synthesis|chemically synthesized]] in [[1866]]. In [[1998]] choline was classified as an [[essential nutrient]] by the [[Food and Nutrition Board]] of the [[Institute of Medicine]] (U.S.A.) and [[Dietary Reference Intake|Adequate Intakes]] (AI) have been established.
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Choline was discovered by Andreas Strecker in [[1864]] and [[chemical synthesis|chemically synthesized]] in [[1866]]. In [[1998]] choline was classified as an [[essential nutrient]] by the [[Food and Nutrition Board]] of the [[Institute of Medicine]] ([[United States|U.S.A.]]).
   
 
==Chemistry==
 
==Chemistry==
'''Choline''' is a [[quaternary ammonium cation|quaternary]] [[saturation (chemistry)|saturated]] [[amine]] with the [[chemical formula]]
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'''Choline''' is a [[quaternary ammonium cation|quaternary]] [[saturation (chemistry)|saturated]] [[amine]] with the [[chemical formula]]: ([[methyl|CH<sub>3</sub>]])<sub>3</sub>[[Nitrogen|N]]<sup>+</sup>[[methylene|CH<sub>2</sub>]][[methylene|CH<sub>2</sub>]][[hydroxyl|OH]]X<sup>−</sup>.
:([[methyl|CH<sub>3</sub>]])<sub>3</sub>[[Nitrogen|N]]<sup>+</sup>[[methylene|CH<sub>2</sub>]][[methylene|CH<sub>2</sub>]][[hydroxyl|OH]]X<sup>−</sup>.
 
 
 
where X<sup>−</sup> is a [[counterion]] such as [[chloride]] (see [[choline chloride]]), [[hydroxyl|hydroxide]] or [[Tartaric acid|tartrate]].
 
where X<sup>−</sup> is a [[counterion]] such as [[chloride]] (see [[choline chloride]]), [[hydroxyl|hydroxide]] or [[Tartaric acid|tartrate]].
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[[Choline chloride]], in mixture with [[urea]] is used as a solvent ( [[deep eutectic solvent|DES]] ) .
   
 
==Physiology==
 
==Physiology==
Choline and its [[metabolites]] are needed for 3 main physiological purposes: structural integrity and signaling roles for cell membranes, cholinergic [[neurotransmission]] ([[acetylcholine]] [[protein biosynthesis|synthesis]]), and as a major source for [[methyl groups]] via its metabolite, [[trimethylglycine]] (betaine) that participates in the [[S-adenosylmethionine]] synthesis [[metabolic pathway|pathways]].
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[[Image:Choline_metabolism.png|thumb|300px|right|Choline metabolism. (Choline is green box at left, second from the bottom.)]]
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Choline and its [[metabolites]] are needed for three main [[physiology|physiological]] purposes: structural integrity and [[cell signaling|signaling]] roles for cell membranes, cholinergic [[neurotransmission]] ([[acetylcholine]] [[protein biosynthesis|synthesis]]), and as a major source for [[methyl group]]s via its metabolite, [[trimethylglycine]] (betaine) that participates in the [[S-adenosylmethionine]] synthesis [[metabolic pathway|pathways]].
   
When choline is metabolized by the body, it may form [[trimethylamine]], a compound with a fishy odor. Hence, when large amounts of choline are taken (such as 10-16 grams/day as a [[dietary supplement]]), the person may suffer from a fishy [[body odor]].
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When choline is [[metabolism|metabolized]] by the [[body]], it may form [[trimethylamine]], a compound with a fishy odor. Hence, when large amounts of choline are taken the person may suffer from a fishy [[body odor]].
   
==Choline as a Supplement==
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==Choline as a supplement==
The [[Food and Drug Administration]] (FDA) requires[http://www.fda.gov/fdac/features/596_baby.html] that infant formula be made from cow's milk containing choline.
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It is well established that supplements of methyl group transfer vitamins [[vitamin B6|B6]], [[vitamin B12|B12]], [[folic acid]] reduce the [[blood]] [[titer]] of [[homocysteine]] and prevent [[cardiovascular disease|heart disease]]. Choline is a necessary source of methyl groups for methyl group transfer. Supplements of [[lecithin]]/choline by Central Soya scientists reduced heart disease in [[clinical trial|laboratory studies]]. The reduction in heart disease with lecithin supplements may however relate more to the [[cholesterol]] carrying capacity of lecithin than to the methyl group transfer role of choline.{{Specify|date=December 2006}}
   
Choline has also found its way into nutritional supplements which claim to reduce [[adipose tissue|body fat]]; but there is little or no evidence to prove that it has any effect on body fat whatsoever.
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Choline supplements are often taken as a form of 'smart drug' or [[nootropic]], due to the role that the neurotransmitter [[acetylcholine]] plays in various [[cognition]] systems within the brain. Choline is a chemical precursor or "building block" needed to produce the neurotransmitter acetylcholine, and research suggests that memory, intelligence and mood are mediated at least in part by acetylcholine metabolism in the brain. The compound's [[quaternary amine]] renders it lipid insoluble and theoretically unable to cross the [[blood-brain barrier]]. However, despite choline's lipid insolubility, a choline transporter exists that allows transport across the blood-brain barrier. The efficacy of these supplements in enhancing cognitive abilities is a topic of continuing debate.
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Some people who practice lucid dreaming use Galantamine with Choline to increase their odds of having a Lucid dream.
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The [[Food and Drug Administration]] (FDA) requires that [[infant formula]] be made from cow's [[milk]] containing choline.<ref>Isadora B. Stehlin, "[http://www.fda.gov/fdac/features/596_baby.html Infant Formula: Second Best but Good Enough]", ''U.S. Food and Drug Administration''.</ref>
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Due to its role in [[lipid metabolism]], choline has also found its way into nutritional supplements which claim to reduce [[adipose tissue|body fat]]; but there is little or no [[scientific evidence|evidence]] to prove that it has any effect on reducing excess body fat or that taking high amounts of choline will increase the rate at which fat is metabolised.
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==Fish Odor Syndrome==
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:''Main article: [[Trimethylaminuria]]''
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Choline is a precurser to [[trimethylamine]], which some persons are not able to break down due to a genetic disorder. Persons suffering from this disorder, called [[Trimethylaminuria]], may suffer from a strong fishy or otherwise unpleasant body odor due to the body's release of odorous trimethylamine. A body odor will occur even on a normal diet - ''i.e.'', one that is not particularly high in choline. Persons with Trimethylaminuria are advised to restrict the intake of foods high in choline; this may help to reduce the sufferer's body odor.
   
 
==Sources==
 
==Sources==
The foods richest in [[lecithin|phosphatidylcholine]] -- the major delivery form of choline -- are beef liver, egg yolks and [[soybean|soy]]. Beef liver, iceberg lettuce, peanut butter, peanuts, sunflower seeds, and cauliflower are some foods that contain free choline. In 2004 USDA has released its first database of the choline content in common foods [http://www.nal.usda.gov/fnic/foodcomp/Data/Choline/Choline.html].
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The foods richest in [[phosphatidylcholine]] the major delivery form of choline are [[egg yolks]], [[soybean|soy]] and cooked [[beef]], [[chicken]], [[veal]] and [[turkey]] livers. Many foods contain trace amounts of free choline, even iceberg [[lettuce]]. To what extent these trace forms are usable by [[absorption (digestive)|human digestion]] is still debated. In [[2004]], the [[United States Department of Agriculture|USDA]] released its first database of the choline content in common foods.<ref>"[http://www.nal.usda.gov/fnic/foodcomp/Data/Choline/Choline.html USDA Database for the Choline Content of Common Foods - 2004]", ''USDA Nutrient Data Laboratory''</ref>
   
The best absorbed choline supplement is lecithin from soy or egg yolk. When scientists at Central Soya Corporation added lecithin/choline supplement to rat chow during the first trimester of pregnancy the supplemented offspring had genius memory compared to rats who did not receive the choline supplement. The effect was lifelong. The effect was traced to enhancement of a part of the brain called the hippocampus.
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The most often available choline [[dietary supplement]] is [[lecithin]], derived from soy or egg yolks, often used as a [[food additive]]. [[Phosphatidylcholine]] is also available as a supplement, in pill or powder form. Supplementary Choline is also available as Choline Chloride, which comes as a liquid due to its hydrophilic properties. Choline chloride is sometimes preferred as a supplement because [[phosphatidylcholine]] can have gastrointestinal side effects.
   
It is well established that supplements of methyl group transfer vitamins B6, B12, folic acid reduce the blood titer of homocystine and prevent heart disease. Choline is a necessary source of methyl groups for methyl group transfer. Supplements of lecithin/choline by Central Soya scientists reduced heart disease in laboratory studies. The reduction in heart disease with lecithin supplements may however relate more to the cholesterol carrying capacity of lecithin than to the methyl group transfer role of choline.
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==Additional images==
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<gallery>
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Image:Choline_Molecule.png|Choline (C5H14NO+)
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Image:Choline chloride.png|[[Choline chloride]]
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Image:Choline hydroxide.png|Choline hydroxide
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Image:Cholina.png|Synthesis
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</gallery>
   
==External links==
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==See also==
*[http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/cho_0283.shtml PDRhealth Choline Description]
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*[[Cholinesterase]]
*[http://www.abc.net.au/rn/talks/8.30/helthrpt/stories/s119524.htm An interview about Choline with Steven Zeisel, Editor-in-Chief of the Journal of Nutritional Biochemistry]
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*[[Succinylcholine]]
*[http://www.nal.usda.gov/fnic/foodcomp/Data/Choline/Choline.html USDA Database for the Choline Content of Common Foods]
 
   
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==References==
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<references/>
   
{{ChemicalSources}}
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{{Vitamin}}
   
[[Category:Amines]]
 
 
[[Category:Alcohols]]
 
[[Category:Alcohols]]
[[Category:Nutrition]]
 
 
[[Category:Dietary supplements]]
 
[[Category:Dietary supplements]]
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[[Category:Nutrition]]
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[[Category:Vitamins]]
   
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Revision as of 23:24, January 28, 2008

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style="background: #F8EABA; text-align: center;" colspan="2" Choline
Choline-skeletal
Identifiers
CAS number 62-49-7
PubChem 305
MeSH Choline
Properties
Molecular formula C5H14NO+
Molar mass 104.171
Hazards
style="background: #F8EABA; text-align: center;" colspan="2" Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references


Choline is an organic compound, classified as an essential nutrient[1][2][3] and usually grouped within the Vitamin B complex. This natural amine is found in the lipids that make up cell membranes and in the neurotransmitter acetylcholine. Adequate intakes (AI) for this micronutrient of between 425 to 550 milligrams daily, for adults, have been established by the Food and Nutrition Board of the Institute of Medicine of the National Academy of Sciences.

History

Choline was discovered by Andreas Strecker in 1864 and chemically synthesized in 1866. In 1998 choline was classified as an essential nutrient by the Food and Nutrition Board of the Institute of Medicine (U.S.A.).

Chemistry

Choline is a quaternary saturated amine with the chemical formula: (CH3)3N+CH2CH2OHX. where X is a counterion such as chloride (see choline chloride), hydroxide or tartrate. Choline chloride, in mixture with urea is used as a solvent ( DES ) .

Physiology

File:Choline metabolism.png

Choline and its metabolites are needed for three main physiological purposes: structural integrity and signaling roles for cell membranes, cholinergic neurotransmission (acetylcholine synthesis), and as a major source for methyl groups via its metabolite, trimethylglycine (betaine) that participates in the S-adenosylmethionine synthesis pathways.

When choline is metabolized by the body, it may form trimethylamine, a compound with a fishy odor. Hence, when large amounts of choline are taken the person may suffer from a fishy body odor.

Choline as a supplement

It is well established that supplements of methyl group transfer vitamins B6, B12, folic acid reduce the blood titer of homocysteine and prevent heart disease. Choline is a necessary source of methyl groups for methyl group transfer. Supplements of lecithin/choline by Central Soya scientists reduced heart disease in laboratory studies. The reduction in heart disease with lecithin supplements may however relate more to the cholesterol carrying capacity of lecithin than to the methyl group transfer role of choline.[specify]


Choline supplements are often taken as a form of 'smart drug' or nootropic, due to the role that the neurotransmitter acetylcholine plays in various cognition systems within the brain. Choline is a chemical precursor or "building block" needed to produce the neurotransmitter acetylcholine, and research suggests that memory, intelligence and mood are mediated at least in part by acetylcholine metabolism in the brain. The compound's quaternary amine renders it lipid insoluble and theoretically unable to cross the blood-brain barrier. However, despite choline's lipid insolubility, a choline transporter exists that allows transport across the blood-brain barrier. The efficacy of these supplements in enhancing cognitive abilities is a topic of continuing debate.

Some people who practice lucid dreaming use Galantamine with Choline to increase their odds of having a Lucid dream.

The Food and Drug Administration (FDA) requires that infant formula be made from cow's milk containing choline.[4]

Due to its role in lipid metabolism, choline has also found its way into nutritional supplements which claim to reduce body fat; but there is little or no evidence to prove that it has any effect on reducing excess body fat or that taking high amounts of choline will increase the rate at which fat is metabolised.

Fish Odor Syndrome

Main article: Trimethylaminuria

Choline is a precurser to trimethylamine, which some persons are not able to break down due to a genetic disorder. Persons suffering from this disorder, called Trimethylaminuria, may suffer from a strong fishy or otherwise unpleasant body odor due to the body's release of odorous trimethylamine. A body odor will occur even on a normal diet - i.e., one that is not particularly high in choline. Persons with Trimethylaminuria are advised to restrict the intake of foods high in choline; this may help to reduce the sufferer's body odor.

Sources

The foods richest in phosphatidylcholine — the major delivery form of choline — are egg yolks, soy and cooked beef, chicken, veal and turkey livers. Many foods contain trace amounts of free choline, even iceberg lettuce. To what extent these trace forms are usable by human digestion is still debated. In 2004, the USDA released its first database of the choline content in common foods.[5]

The most often available choline dietary supplement is lecithin, derived from soy or egg yolks, often used as a food additive. Phosphatidylcholine is also available as a supplement, in pill or powder form. Supplementary Choline is also available as Choline Chloride, which comes as a liquid due to its hydrophilic properties. Choline chloride is sometimes preferred as a supplement because phosphatidylcholine can have gastrointestinal side effects.

Additional images

See also

References

  1. Jane Higdon, "Choline", Micronutrient Information Center, Linus Pauling Institute
  2. "Choline, PDRHealth
  3. "Choline" (An interview with Steven Zeisel, Editor-in-Chief of the Journal of Nutritional Biochemistry), Radio National Health Report with Norman Swan, Monday 17 April 2000
  4. Isadora B. Stehlin, "Infant Formula: Second Best but Good Enough", U.S. Food and Drug Administration.
  5. "USDA Database for the Choline Content of Common Foods - 2004", USDA Nutrient Data Laboratory


Vitamins
All B vitamins | All D vitamins
Retinol (A) | Thiamine (B1) | Riboflavin (B2) | Niacin (B3) | Pantothenic acid (B5) | Pyridoxine (B6) | Biotin (B7) | Folic acid (B9) | Cyanocobalamin (B12) | Ascorbic acid (C) | Ergocalciferol (D2) | Cholecalciferol (D3) | Tocopherol (E) | Naphthoquinone (K)
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