| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:33:40 UTC |
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| Update date | 2017-01-19 02:36:43 UTC |
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| FoodComEx ID | PC000979 |
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| FoodDB Record | FDB021910 |
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| Chemical Information |
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| Name | L-Palmitoylcarnitine |
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| Description | L-Palmitoylcarnitine is a long-chain acyl fatty acid derivative ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids. L-palmitoylcarnitine, due to its amphipatic character is, like detergents, a surface-active molecule and by changing the membrane fluidity and surface charge can change activity of several enzymes and transporters localized in the membrane. L-palmitoylcarnitine has been also reported to change the activity of certain proteins. On the contrary to carnitine, palmitoylcarnitine was shown to stimulate the activity of caspases 3, 7 and 8 and the level of this long-chain acylcarnitine increased during apoptosis. Palmitoylcarnitine was also reported to diminish completely binding of phorbol esters, the protein kinase C activators and to decrease the autophosphorylation of the enzyme. Apart from these isoform nonspecific phenomena, palmitoylcarnitine was also shown to be responsible for retardation in cytoplasm of protein kinase C isoforms β and δ and, in the case of the latter one, to decrease its interaction with GAP-43.
Some of the physico-chemical properties of palmitoylcarnitine may help to explain the need for coenzyme A-carnitine-coenzyme A acyl exchange during mitochondrial fatty acid import. The amphiphilic character of palmitoylcarnitine may also explain its proposed involvement in the pathogenesis of myocardial ischemia.
L-Palmitoylcarnitine accumulates in ischemic myocardium and potentially contribute to myocardial damage through alterations in membrane molecular dynamics , one mechanism through which could play an important role in ischemic injury. Palmitoylcarnitine is characteristically elevated in carnitine palmitoyltransferase II deficiency, late-onset (OMIM 255110). (PMID 2540838, 15363641, 8706815) [HMDB] |
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| CAS Number | 2364-67-2 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| (+)-palmitoylcarnitine | hmdb | | (3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoate | ChEBI | | (3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid | Generator | | (3S)-3-hexadecanoyloxy-4-(trimethylammonio)butanoate | hmdb | | (3S)-3-hexadecanoyloxy-4-(trimethylammonio)butanoic acid | hmdb | | (3S)-3-palmitoyloxy-4-(trimethylammonio)butanoate | hmdb | | (3S)-3-palmitoyloxy-4-(trimethylammonio)butanoic acid | hmdb | | 3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-Propanaminium | hmdb | | D-palmitylcarnitine | hmdb | | Hexadecanoyl-L-carnitine | hmdb | | Hexadecanoylcarnitine | ChEBI | | Hexadecenoyl carnitine | hmdb | | L-carnitine palmitoyl ester | hmdb | | L-palmitoyl-L-carnitine | hmdb | | L(-)-Palmitylcarnitine | hmdb | | O-Hexadecanoyl-(R)-carnitine | ChEBI | | O-Hexadecanoyl-R-carnitine | ChEBI | | Palmitoyl d-carnitine | hmdb | | Palmitoyl-(-)-carnitine | hmdb | | Palmitoyl-L-carnitine | hmdb | | Palmitoylcarnitine | ChEBI | | Palmityl-L-carnitine | hmdb |
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| Chemical Formula | C23H45NO4 |
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| IUPAC name | (3R)-3-(hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate |
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| InChI Identifier | InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1 |
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| InChI Key | XOMRRQXKHMYMOC-OAQYLSRUSA-N |
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| Isomeric SMILES | CCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C |
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| Average Molecular Weight | 399.6077 |
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| Monoisotopic Molecular Weight | 399.334858933 |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Fatty acid esters |
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| Direct Parent | Acyl carnitines |
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| Alternative Parents | |
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| Substituents | - Acyl-carnitine
- Dicarboxylic acid or derivatives
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Carboxylic acid ester
- Carboxylic acid salt
- Carboxylic acid derivative
- Carboxylic acid
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic salt
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Amine
- 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 | Not Available | |
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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 50 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 |
