Nisinic acid

Nisinic acid
Names
	Preferred IUPAC name (6Z,9Z,12Z,15Z,18Z,21Z)-Tetracosa-6,9,12,15,18,21-hexaenoic acid
	Other names all-cis-6,9,12,15,18,21-tetracosahexaenoic acid
Identifiers
CAS Number	68378-49-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	9967286;
PubChem CID	11792612;
UNII	L8L6GYZ1ZX ;
CompTox Dashboard (EPA)	DTXSID801318739 ;
	InChI InChI=1S/C24H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-23H2,1H3,(H,25,26)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18- Key: YHGJECVSSKXFCJ-KUBAVDMBSA-N;
	SMILES CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O;
Properties
Chemical formula	C24H36O2
Molar mass	356.550 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Nisinic acid is a very long chain polyunsaturated omega-3 fatty acid, similar to docosahexaenoic acid (DHA). The lipid name is 24:6 (n-3) and the chemical name is all-cis-6,9,12,15,18,21-tetracosahexaenoic acid. It is not well studied, but polyunsaturated fatty acids even longer than DHA, nisinic acid included, may hold scientific promise.^[1]^[vague] It has biological activity and is involved in the formation of DHA, but the mechanisms are still under research.^[2]^[3]^[4]^[5]

References

↑ Vyssotski, M. (2011). "Nisinic acid, 24: 6n-3, and other methylene-interrupted very long chain polyunsaturated fatty acids". In Paige L. Gilmore (ed.). Lipids: Categories, Biological Functions and Metabolism, Nutrition and Health. Nova Science Publishers. pp. 199–216. ISBN 978-1-61668-464-8. Archived from the original on 2023-06-18. Retrieved 2017-03-22.
↑ Gotoh, Naohiro; Nagao, Koji; Ishida, Hiroki; Nakamitsu, Kazusa; Yoshinaga, Kazuaki; Nagai, Toshiharu; Beppu, Fumiaki; Yoshinaga-Kiriake, Aya; Watanabe, Hiroyuki; Yanagita, Teruyoshi (2018). "Metabolism of Natural Highly Unsaturated Fatty Acid, Tetracosahexaenoic Acid (24:6n-3), in C57BL/KsJ-db/db Mice". Journal of Oleo Science. 67 (12): 1597–1607. doi:10.5650/jos.ess18167.
↑ Metherel, Adam H.; Bazinet, Richard P. (2019-10-01). "Updates to the n-3 polyunsaturated fatty acid biosynthesis pathway: DHA synthesis rates, tetracosahexaenoic acid and (minimal) retroconversion". Progress in Lipid Research. 76 101008. doi:10.1016/j.plipres.2019.101008. ISSN 0163-7827.
↑ Metherel, Adam H.; Domenichiello, Anthony F.; Kitson, Alex P.; Lin, Yu-Hong; Bazinet, Richard P. (2017-02-01). "Serum n-3 Tetracosapentaenoic Acid and Tetracosahexaenoic Acid Increase Following Higher Dietary α-Linolenic Acid but not Docosahexaenoic Acid". Lipids. 52 (2): 167–172. doi:10.1007/s11745-016-4223-0. ISSN 1558-9307.
↑ Rotarescu, Ruxandra D.; Rezaei, Kimia; Mutch, David M.; Metherel, Adam H. (2022-10-01). "Increases in plasma n-3 tetracosapentaenoic acid and tetracosahexaenoic acid following 12 weeks of EPA, but not DHA, supplementation in women and men". Prostaglandins, Leukotrienes and Essential Fatty Acids. 185 102494. doi:10.1016/j.plefa.2022.102494. ISSN 0952-3278.

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[1] Vyssotski, M. (2011). "Nisinic acid, 24: 6n-3, and other methylene-interrupted very long chain polyunsaturated fatty acids". In Paige L. Gilmore (ed.). Lipids: Categories, Biological Functions and Metabolism, Nutrition and Health. Nova Science Publishers. pp. 199–216. ISBN 978-1-61668-464-8. Archived from the original on 2023-06-18. Retrieved 2017-03-22.

[2] Gotoh, Naohiro; Nagao, Koji; Ishida, Hiroki; Nakamitsu, Kazusa; Yoshinaga, Kazuaki; Nagai, Toshiharu; Beppu, Fumiaki; Yoshinaga-Kiriake, Aya; Watanabe, Hiroyuki; Yanagita, Teruyoshi (2018). "Metabolism of Natural Highly Unsaturated Fatty Acid, Tetracosahexaenoic Acid (24:6n-3), in C57BL/KsJ-db/db Mice". Journal of Oleo Science. 67 (12): 1597–1607. doi:10.5650/jos.ess18167.

[3] Metherel, Adam H.; Bazinet, Richard P. (2019-10-01). "Updates to the n-3 polyunsaturated fatty acid biosynthesis pathway: DHA synthesis rates, tetracosahexaenoic acid and (minimal) retroconversion". Progress in Lipid Research. 76 101008. doi:10.1016/j.plipres.2019.101008. ISSN 0163-7827.

[4] Metherel, Adam H.; Domenichiello, Anthony F.; Kitson, Alex P.; Lin, Yu-Hong; Bazinet, Richard P. (2017-02-01). "Serum n-3 Tetracosapentaenoic Acid and Tetracosahexaenoic Acid Increase Following Higher Dietary α-Linolenic Acid but not Docosahexaenoic Acid". Lipids. 52 (2): 167–172. doi:10.1007/s11745-016-4223-0. ISSN 1558-9307.

[5] Rotarescu, Ruxandra D.; Rezaei, Kimia; Mutch, David M.; Metherel, Adam H. (2022-10-01). "Increases in plasma n-3 tetracosapentaenoic acid and tetracosahexaenoic acid following 12 weeks of EPA, but not DHA, supplementation in women and men". Prostaglandins, Leukotrienes and Essential Fatty Acids. 185 102494. doi:10.1016/j.plefa.2022.102494. ISSN 0952-3278.

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References