Choline

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Choline

Choline is an organic compound

Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
, classified as a water-soluble essential nutrient

Essential nutrient

An essential nutrient is a nutrient required for normal body functioning that cannot be synthesized by the body and thus must be obtained from a Diet source....
and usually grouped within the Vitamin B complex. This natural amine

Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
is found in the lipids that make up cell membranes and in the neurotransmitter

Neurotransmitter

Neurotransmitters are chemistry which relay, amplify and modulate signals between a neuron and another cell . Neurotransmitters are packaged into vesicles that cluster beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to receptors in the membrane on the postsynaptic side of...
acetylcholine

Acetylcholine

The chemical compound acetylcholine is a neurotransmitter in both the peripheral nervous system and central nervous system in many organisms including homo sapiens....
. Adequate intakes (AI) for this micronutrient

Micronutrient

Micronutrients are nutrients needed for life in small quantities. The Microminerals or trace elements include at least iron, cobalt, chromium, copper, iodine, manganese, selenium, zinc and molybdenum....
of between 425 to 550 milligrams daily, for adults, have been established by the Food and Nutrition Board of the Institute of Medicine

Institute of Medicine

The Institute of Medicine , one of the United States National Academies, is a Non-profit organization, non-governmental United States organization chartered in 1970 as a part of the United States National Academy of Sciences....
of the National Academy of Sciences

United States National Academy of Sciences

The National Academy of Sciences is a corporation in the United States whose members serve pro bono as "advisers to the nation on science, engineering, and medicine."...
.

ine was discovered by Andreas Strecker in 1864 and chemically synthesized

Chemical synthesis

In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product , or several products. This happens by physics and chemical manipulations usually involving one or more reactions....
in 1866.

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Encyclopedia

Choline is an organic compound

Organic compound

Essential nutrient

Amine

Neurotransmitter

Acetylcholine

Micronutrient

Institute of Medicine

United States National Academy of Sciences

The National Academy of Sciences is a corporation in the United States whose members serve pro bono as "advisers to the nation on science, engineering, and medicine."...
.

History

Choline was discovered by Andreas Strecker in 1864 and chemically synthesized

Chemical synthesis

Essential nutrient

An essential nutrient is a nutrient required for normal body functioning that cannot be synthesized by the body and thus must be obtained from a Diet source....
by the Food and Nutrition Board of the Institute of Medicine

Institute of Medicine

United States

The United States of America is a Federal government constitutional republic comprising U.S. state and a federal district. The country is situated mostly in central North America, where its Contiguous United States and Washington, D.C., the Capital districts and territories, lie between the Pacific Ocean and Atlantic Oceans, Borders of the U...
).

Chemistry

Choline is a quaternary

Quaternary ammonium cation

Quaternary ammonium cations, also known as quats, are positively electric charge polyatomic ions of the structure NR4+ with R being alkyl groups....
saturated

Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
amine

Amine

Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
(CH₃)₃N

Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
⁺CH₂

Methylene

Methylene is the chemical species, R2C:, named after methane, in which two of the carbon atom's valence electrons form no bonds. The word is applicable to:...
CH₂

Methylene

Methylene is the chemical species, R2C:, named after methane, in which two of the carbon atom's valence electrons form no bonds. The word is applicable to:...
OH

Hydroxyl

Hydroxyl in chemistry stands for a molecule consisting of an oxygen atom and a hydrogen atom connected by a covalent bond. The neutral form is a hydroxyl Radical and the hydroxyl anion is called a hydroxide....
X^-, where X^- is a counterion

Counterion

A counterion is the ion that accompanies an ionic species in order to maintain electric neutrality. In table salt the sodium cation is the counterion for the chlorine anion and vice versa....
such as chloride

Chloride

The chloride ion is formed when the chemical element chlorine picks up one electron to form an anion Cl−....
(see choline chloride

Choline chloride

Choline chloride or 2-hydroxy-N,N,N-trimethylethanaminium chloride is an organic compound and a quaternary ammonium salt. It has a choline cation with chloride anion....
), hydroxide

Hydroxyl

Tartaric acid

Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes, bananas, and tamarinds, and is one of the main acids found in wine....
. Choline chloride

Choline chloride

Choline chloride or 2-hydroxy-N,N,N-trimethylethanaminium chloride is an organic compound and a quaternary ammonium salt. It has a choline cation with chloride anion....
, in mixture with urea

Urea

Urea is an organic compound with the chemical formula 2carbonoxygen.Urea is also known by the International Nonproprietary Name carbamide, as established by the World Health Organization....
is used as a solvent ( DES

Deep eutectic solvent

A deep eutectic solvent or DES is a type of Ion solvent with special properties composed of a mixture which forms a eutectic with a melting point much lower than either of the individual components....
) and the salicylate salt is used topically for pain relief of aphthous ulcer

Aphthous ulcer

An aphthous ulcer, also known as canker sore, is a type of oral ulcer, which presents as a painful open sore inside the mouth or upper throat, caused by a break in the mucous membrane....
s.

Physiology

Choline and its metabolites are needed for three main physiological

Physiology

Physiology is the study of the mechanical, physical, and biochemical functions of living organisms. Physiology has traditionally been divided between plant physiology and animal and all living things physiology but the principles of physiology are universal, no matter what particular organism is being studied....
purposes: structural integrity and signaling

Cell signaling

Cell signaling is part of a complex system of communication that governs basic cellular activities and coordinates cell actions. The ability of cells to perceive and correctly respond to their microenvironment is the basis of development, tissue repair, and immunity as well as normal tissue homeostasis....
roles for cell membranes, cholinergic neurotransmission

Neurotransmission

Neurotransmission , also called synaptic transmission, is an electrical movement within synapses caused by a propagation of nerve impulses....
(acetylcholine

Acetylcholine

The chemical compound acetylcholine is a neurotransmitter in both the peripheral nervous system and central nervous system in many organisms including homo sapiens....
synthesis

Protein biosynthesis

Protein synthesis is the process in which cell build proteins. The term is sometimes used to refer only to protein translation but more often it refers to a multi-step process, beginning with amino acid synthesis and transcription which are then used for translation ....
), and as a major source for methyl group

Methyl group

In chemistry, a methyl group is a hydrophobic alkyl functional group named after methane . It has the chemical formula -3 and is often abbreviated -Me....
s via its metabolite, trimethylglycine

Trimethylglycine

Trimethylglycine , is an organic compound described by the chemical formula 3N+CH2CO2H. Trimethylglycine was originally named betaine after its discovery in sugar beets in the 19th century....
(betaine) that participates in the S-adenosylmethionine synthesis pathways

Metabolic pathway

In biochemistry, a metabolic pathway is a series of chemistry reactions occurring within a cell . In each pathway, a principal chemical is modified by chemical reactions....
.

When choline is metabolized

Metabolism

Metabolism is the set of chemical reactions that occur in living organisms in order to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments....
by the body

Body

With regard to organism, a body is the integral physical material of an individual. "Body" often is used in connection with appearance, health issues and death....
, it may form trimethylamine

Trimethylamine

Trimethylamine is an organic compound with the formula N3. This colorless, hygroscopic, and flammable tertiary amine has a strong "fishy" odor in low concentrations and an ammonia-like odor at higher concentrations....
, a compound with a fishy odor. Hence, when large amounts of choline are taken the person may suffer from a fishy body odor

Body odor

Body odor , often abbreviated as B.O., or bromhidrosis is the odor of bacterium growing on the body. These bacteria multiply rapidly in the presence of sweat, but sweat itself is almost completely odorless....
.

Choline as a supplement

It is well established that supplements of methyl group transfer vitamins B6

Vitamin B6

Vitamin B6 is a water-soluble vitamin and is part of the vitamin B complex group. Pyridoxal phosphate is the active form and is a cofactor in many reactions of amino acid metabolism, including transamination, deamination, and decarboxylation....
, B12

Vitamin B12

Vitamin B12 is a water soluble vitamin with a key role in the normal functioning of the brain and nervous system, and for the formation of blood....
, folic acid

Folic acid

Folic acid and Folate are forms of the water-soluble B vitamins. Vitamin B9 is essential to numerous bodily functions ranging from nucleotide synthesis to the remethylation of homocysteine....
reduce the blood

Blood

Blood is a specialized bodily fluid that delivers necessary substances to the body's Cell s ? such as nutrients and oxygen ? and transports waste products away from those same cells....
titer

Titer

A titer is a measure of concentration. Titer testing employs Serial_dilution to obtain approximate quantitative information from an analytical procedure that inherently only evaluates as positive or negative....
of homocysteine

Homocysteine

Homocysteine is an amino acid with the formula HSCH2CH2CHCO2H. It is a homologous series of the amino acid cysteine, differing by an additional methylene group....
and prevent heart disease

Cardiovascular disease

Cardiovascular disease or cardiovascular diseases refers to the class of diseases that involve the heart or blood vessels . While the term technically refers to any disease that affects the Circulatory system , it is usually used to refer to those related to atherosclerosis ....
. Choline is a necessary source of methyl groups for methyl group transfer. Supplements of lecithin

Lecithin

Lecithin is any of a group of yellow-brownish fatty substances occurring in animal and plant tissues, and in egg yolk, composed of phosphoric acid, choline, fatty acids, glycerol, glycolipids, triglycerides, and phospholipids ....
/choline by Central Soya scientists reduced heart disease in laboratory studies

Clinical trial

In health care, clinical trials are conducted to allow safety and efficacy data to be collected for new drugs or devices. These trials can only take place once satisfactory information has been gathered on the quality of the product and its non-clinical safety, and Institutional review board approval is granted in the country where the trial...
. The reduction in heart disease with lecithin supplements may however relate more to the cholesterol

Cholesterol

Cholesterol is a lipidic, waxy alcohol found in the cell membranes and transported in the blood plasma of all animals. It is an essential component of mammalian cell membranes where it is required to establish proper membrane permeability and membrane fluidity....
carrying capacity of lecithin than to the methyl group transfer role of choline.

Choline supplements are often taken as a form of 'smart drug' or nootropic

Nootropic

Memory enhancers are often referred to as "smart drugs", "study drugs", "smart nutrients", "cognitive enhancers", "brain enhancers" or in the scientific literature as nootropics....
, due to the role that the neurotransmitter acetylcholine

Acetylcholine

The chemical compound acetylcholine is a neurotransmitter in both the peripheral nervous system and central nervous system in many organisms including homo sapiens....
plays in various cognition

Cognition

Cognition is the science term for "the process of thought."Its usage varies in different ways in accord with different disciplines: For example, in psychology and cognitive science it refers to an information processing view of an individual's psychological Functionalism s....
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 which might suggest it would be unable to cross the blood-brain barrier

Blood-brain barrier

The blood-brain barrier is a metabolic or cellular structure in the central nervous system that restricts the passage of various chemical substances and microscopic objects between the bloodstream and the neural tissue itself, while still allowing the passage of substances essential to metabolism function ....
. 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

Lucid dreaming

A lucid dream is a dream in which the person is aware that they are dreaming while the dream is in progress, also known as a conscious dream....
use Galantamine

Galantamine

'Galantamine' is a drug used for the treatment of mild to moderate Alzheimer?s disease and various memory impairments. It is an alkaloid that is obtained synthetically or from the bulbs and flowers of the Caucasian snowdrop , Galanthus woronowii and related genera like Narcissus , Leucojum and Lycoris including Lycoris radi...
with choline bitartrate or Alpha-GPC in the belief it may increase their odds of having a lucid dream. Acetylcholine precursors such as choline work synergistically with Galantamine to help improve memory and fight the symptoms of Alzheimer's Disease (AD).

The Food and Drug Administration

Food and Drug Administration

The U.S. Food and Drug Administration is an Government agency of the United States Department of Health and Human Services and is responsible for regulating and supervising the safety of foods, dietary supplements, Medications, vaccines, Biopharmaceutical, blood transfusion, medical devices, Electromagnetic radiation-emitting devices, veteri...
(FDA) requires that infant formula

Infant formula

Infant formula is an artificial substitute for human breast milk, intended for infant consumption. The first preparations for the feeding of infants were produced commercially in 1867 by Justus von Liebig....
not made from cow's milk

Milk

Milk is an opaque white liquid produced by the mammary glands of female mammals . It provides the primary source of nutrition for newborn mammals before they are able to digestion other types of food....
be supplemented with choline.

Due to its role in lipid metabolism

Lipid metabolism

Lipid metabolism refers to the processes that involve the creation and degradation of lipids.The types of lipids involved include:* bile salts...
, choline has also found its way into nutritional supplements which claim to reduce body fat

Adipose tissue

In histology, adipose tissue or fat is loose connective tissue composed of adipocytes. Adipose tissue is derived from lipoblasts. Its main role is to store energy in the form of fat, although it also cushions and Thermal insulation the body....
; but there is little or no evidence

Scientific evidence

Scientific evidence is evidence which serves to either support or counter a scientific theory or hypothesis . Such evidence is expected to be empirical and properly documented in accordance with scientific method such as is applicable to the particular field of inquiry ....
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

Choline is a precursor to trimethylamine

Trimethylamine

Trimethylamine is an organic compound with the formula N3. This colorless, hygroscopic, and flammable tertiary amine has a strong "fishy" odor in low concentrations and an ammonia-like odor at higher concentrations....
, which some persons are not able to break down due to a genetic disorder. Persons suffering from this disorder, called trimethylaminuria

Trimethylaminuria

Trimethylaminuria , also known as fish odor syndrome or fish malodor syndrome, is a rare inborn error of metabolism that causes a defect in the normal production of the enzyme Flavin containing monooxygenase 3 ....
, 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.

Choline hydroxide

Choline hydroxide is one of the class of phase transfer catalyst

Phase transfer catalyst

A phase transfer catalyst or PTC in chemistry is a catalyst which facilitates the migration of a reactant in a heterogeneous system from one phase into another phase where reaction can take place....
s which are used to carry the hydroxide

Hydroxide

In chemistry, hydroxide is the name for the Diatomic molecule anion OH-, consisting of oxygen and hydrogen atoms, usually derived from the Dissociation of a base ....
ion into organic systems. It is far and away the least costly phase transfer catalyst, and gets a lot of use in stripping photoresists in printed circuit board production. Choline hydroxide is not completely stable and it spontaneously, slowly breaks down to release trimethylamine

Trimethylamine

Sources

The foods richest in phosphatidylcholine

Phosphatidylcholine

Phosphatidylcholines are a class of phospholipids which incorporate choline as a headgroup.They are a major component of biological membranes and can be isolated from either egg yolk or soy beans from which they are mechanically extracted or chemically extracted using hexane....
— the major delivery form of choline — are egg yolks, soy

Soybean

The soybean or soya bean is a species of legume native to East Asia. The plant is classed as an oilseed rather than a Pulse . It is an annual plant that has been used in China for 5,000 years as a food and a component of drugs....
and cooked beef

Beef

Beef is the culinary name for meat from bovines, especially domestic cattle . Beef is one of the principal meats used in the cuisine of Australia, European cuisine and the Americas, and is also important in Africa, East Asia, and Southeast Asia....
, chicken

Chicken

The chicken is a Domestication fowl. Recent evidence suggests that domestication of the chicken was under way in Vietnam over 10,000 years ago....
, veal

Veal

Veal is the meat of calves . Though veal can be produced from any calf, most veal comes from male calves of dairy cattle breeds. Compared to other meats, veal has a delicate taste and tender texture....
and turkey

Turkey

Turkey , known officially as the Republic of Turkey , is a Eurasian country that stretches across the Anatolian peninsula in southwest Asia and Thrace in the Balkans region of Southern Europe....
livers. Many foods contain trace amounts of free choline, even iceberg lettuce

Lettuce

Lettuce is a temperate annual plant or biennial plant of the daisy family Asteraceae. It is most often grown as a leaf vegetable. In many countries, it is typically eaten cold, raw, in salads, hamburgers, tacos, and in many other dishes....
. To what extent these trace forms are usable by human digestion is still debated. In 2004, the USDA

United States Department of Agriculture

The United States Department of Agriculture is the United States federal executive departments responsible for developing and executing Federal government of the United States policy on farming, agriculture, and food....
released its first database of the choline content in common foods.

The most often available choline dietary supplement

Dietary supplement

A dietary supplement, also known as food supplement or nutritional supplement, is a preparation intended to provide nutrients, such as vitamins, Dietary minerals, fatty acids or amino acids, that are missing or are not consumed in sufficient quantity in a person's diet ....
is lecithin

Lecithin

Lecithin is any of a group of yellow-brownish fatty substances occurring in animal and plant tissues, and in egg yolk, composed of phosphoric acid, choline, fatty acids, glycerol, glycolipids, triglycerides, and phospholipids ....
, derived from soy or egg yolks, often used as a food additive

Food additive

Food additives are substances added to food to preserve flavour or improve its taste and appearance.Some additives have been used for centuries; for example, preserving food by pickling , edible salting, as with bacon, preserving sweets or using sulfur dioxide as in some wines....
. 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.
Although the human body can make some choline it is generally recognized that it is important to get dietary choline as well. Although most foods have at least a little choline, some people may have to pay more close attention to get enough in their diets, particularly if they do not eat many whole eggs.

Choline

History

Chemistry

Physiology

Choline as a supplement

Fish odor syndrome

Choline hydroxide

Sources

Additional images