| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:28:45 UTC |
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| Update date | 2017-01-19 02:36:13 UTC |
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| FoodComEx ID | PC000134 |
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| FoodDB Record | FDB000710 |
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| Chemical Information |
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| Name | Choline |
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| Description | Choline, also known as bilineurine, is an organic compound containing a N, N, N-trimethylethanolammonium cation. Choline is an extremely weak basic (essentially neutral) compound (based on its pKa). Choline is 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. In plants, the first step in de novo biosynthesis of choline involves the decarboxylation of serine into ethanolamine, which is catalyzed by a serine decarboxylase. The synthesis of choline from ethanolamine involves three consecutive N-methylation steps catalyzed by a methyl transferase. In terms of human health, choline is now considered to be an essential vitamin. While humans can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must be consumed in the diet to maintain health. Required levels are between 425 mg/day (female) and 550 mg/day (male). Milk, eggs, liver, and peanuts are especially rich in choline. Most choline is found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (i.e. conversion of homocysteine into methionine). Lack of sufficient amounts of choline in the diet can lead to fatty liver disease and general liver damage. This arises from the lack of VLDL , which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine amino transferase and is associated with increased incidence of liver cancer. |
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| CAS Number | 62-49-7 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| (2-Hydroxyethyl)trimethyl ammonium | biospider | | (2-Hydroxyethyl)trimethylammonium | HMDB | | (beta-Hydroxyethyl)trimethylammonium | biospider | | 2-Hydroxy-N,N,N-trimethyl-ethanaminium | HMDB | | 2-Hydroxy-N,N,N-trimethylethanaminium | HMDB | | 2-Hydroxy-N,N,N-trimethylethanaminium(1+), 9CI | db_source | | 2-Hydroxyethyl-trimethylazanium | biospider | | Amanitin? | db_source | | Arachine | db_source | | Araquine | db_source | | Bilineurine | db_source | | Choline (8CI) | biospider | | Choline cation | HMDB | | Choline ion | biospider | | Cholinum | HMDB | | Ethanaminium, 2-hydroxy-N,N,N-trimethyl- (9CI) | biospider | | Hormocline | HMDB | | N-Trimethylethanolamine | ChEBI | | N,N,N-Trimethylethanol-ammonium | biospider | | N,N,N-Trimethylethanolammonium | HMDB | | Neocolina | HMDB | | Sincalin | db_source | | Sinkalin | db_source | | Trimethylethanolamine | ChEBI |
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| Chemical Formula | C5H14NO |
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| IUPAC name | (2-hydroxyethyl)trimethylazanium |
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| InChI Identifier | InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 |
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| InChI Key | OEYIOHPDSNJKLS-UHFFFAOYSA-N |
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| Isomeric SMILES | C[N+](C)(C)CCO |
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| Average Molecular Weight | 104.1708 |
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| Monoisotopic Molecular Weight | 104.107539075 |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation. |
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| Kingdom | Organic compounds |
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| Super Class | Organic nitrogen compounds |
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| Class | Organonitrogen compounds |
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| Sub Class | Quaternary ammonium salts |
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| Direct Parent | Cholines |
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| Alternative Parents | |
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| Substituents | - Choline
- Tetraalkylammonium salt
- 1,2-aminoalcohol
- Alkanolamine
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organic salt
- Primary alcohol
- Organooxygen compound
- Amine
- Alcohol
- Organic cation
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | 302-303 oC (Chloride salt) | |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 300 mg |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| Not Available |
