Palmitoylcarnitine

Palmitoylcarnitine
Names
	IUPAC name 3-(palmitoyloxy)-4-(trimethylammonio)butanoate
Identifiers
CAS Number	1935-18-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL301722 ;
ChemSpider	448 ;
MeSH	Palmitoylcarnitine
PubChem CID	461;
UNII	U8K6DKA8V2 ;
CompTox Dashboard (EPA)	DTXSID90895028 ;
	InChI 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 Key: XOMRRQXKHMYMOC-UHFFFAOYSA-N ; InChI=1/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 Key: XOMRRQXKHMYMOC-UHFFFAOYAU;
	SMILES [O-]C(=O)CC(OC(=O)CCCCCCCCCCCCCCC)C[N+](C)(C)C;
Properties
Chemical formula	C23H45NO4
Molar mass	399.608 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Palmitoylcarnitine is an ester derivative of carnitine involved in the metabolism of fatty acids. During the tricarboxylic acid cycle (TCA), fatty acids undergo a process known as β-oxidation to produce energy in the form of ATP. β-oxidation occurs primarily within mitochondria, however the mitochondrial membrane prevents the entry of long chain fatty acids (>C10), so the conversion of fatty acids such as palmitic acid is key.^[1] Palmitic acid is brought to the cell and once inside the cytoplasm is first converted to Palmitoyl-CoA. Palmitoyl-CoA has the ability to freely pass the outer mitochondrial membrane, but the inner membrane is impermeable to the Acyl-CoA and thioester forms of various long-chain fatty acids such as palmitic acid. The palmitoyl-CoA is then enzymatically transformed into palmitoylcarnitine via the Carnitine O-palmitoyltransferase family. The palmitoylcarnitine is then actively transferred into the inner membrane of the mitochondria via the carnitine-acylcarnitine translocase.^[2] Once inside the inner mitochondrial membrane, the same Carnitine O-palmitoyltransferase family is then responsible for transforming the palmitoylcarnitine back to the palmitoyl-CoA form.

^ Tein, Ingrid (2015-01-01), Darras, Basil T.; Jones, H. Royden; Ryan, Monique M.; De Vivo, Darryl C. (eds.), "Chapter 40 - Lipid Storage Myopathies Due to Fatty Acid Oxidation Defects", Neuromuscular Disorders of Infancy, Childhood, and Adolescence (Second Edition), San Diego: Academic Press, pp. 761–795, doi:10.1016/b978-0-12-417044-5.00040-8, ISBN 978-0-12-417044-5
^ Pande, S. V. (1975-03-01). "A mitochondrial carnitine acylcarnitine translocase system". Proceedings of the National Academy of Sciences. 72 (3): 883–887. Bibcode:1975PNAS...72..883P. doi:10.1073/pnas.72.3.883. ISSN 0027-8424. PMC 432425. PMID 1055387.

[1] Tein, Ingrid (2015-01-01), Darras, Basil T.; Jones, H. Royden; Ryan, Monique M.; De Vivo, Darryl C. (eds.), "Chapter 40 - Lipid Storage Myopathies Due to Fatty Acid Oxidation Defects", Neuromuscular Disorders of Infancy, Childhood, and Adolescence (Second Edition), San Diego: Academic Press, pp. 761–795, doi:10.1016/b978-0-12-417044-5.00040-8, ISBN 978-0-12-417044-5

[2] Pande, S. V. (1975-03-01). "A mitochondrial carnitine acylcarnitine translocase system". Proceedings of the National Academy of Sciences. 72 (3): 883–887. Bibcode:1975PNAS...72..883P. doi:10.1073/pnas.72.3.883. ISSN 0027-8424. PMC 432425. PMID 1055387.

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