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Nisinic acid

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(Redirected fromTetracosahexaenoic 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^Y
3D model (JSmol)	Interactive image
ChemSpider	9967286
PubChem CID	11792612
UNII	L8L6GYZ1ZX^Y
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 theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Nisinic acid is a very long chainpolyunsaturated omega-3 fatty acid, similar todocosahexaenoic acid (DHA). The lipid name is 24:6 (n-3) and the chemical name isall-cis-6,9,12,15,18,21-tetracosahexaenoic acid. It is not well studied, butpolyunsaturated 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

[edit]

^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 9781616684648.
^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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