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Structure Database (LMSD)

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Common Name

THA

Systematic Name

6Z,9Z,12Z,15Z,18Z,21Z-tetracosahexaenoic acid

Synonyms

Nisinic acid
C24:6n-3,6,9,12,15,18
24:6n3

LM ID

LMFA01030822

Formula

C₂₄H₃₆O₂

Exact Mass

Calculate m/z

356.27153

Sum Composition

FA 24:6

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

6(Z),9(Z),12(Z),15(Z),18(Z),21(Z)-Tetracosahexaenoic acid is a very long chain polyunsaturated fatty acid (VLCPUFA) that has been found in tunny, herring, cod-liver, pilot whale, sardine, and squalus-suclii-liver oils, bovine retina, and as a component of triglycerides and cholesterol esters in mouse and rat testis.^1,2,3 It is produced from dietary linolenic acid via a series of elongation and Δ6-desaturation reactions in fish and rat brain and undergoes β-oxidation to form docosahexaenoic acid (DHA).^4,5

This information has been provided by Cayman Chemical

References

1. Mourente, G., and Tocher, D.R. In vivo metabolism of [1-14C]linolenic acid (18:3(n-3)) and [1-14C]eicosapentaenoic acid (20:5(n-3)) in a marine fish: Time-course of the desaturation/elongation pathway. Biochim. Biophys. Acta 1212(1), 109-118 (1994).

2. Williard, D.E., Harmon, S.D., Kaduce, T.L., et al. Docosahexaenoic acid synthesis from n-3 polyunsaturated fatty acids in differentiated rat brain astrocytes. J. Lipid Res. 42(9), 1368-1376 (2001).

3. Furland, N.E., Maldonado, E.N., and Aveldaño, M.I. Very long chain PUFA in murine testicular triglycerides and cholesterol esters. Lipids 38(1), 73-80 (2003).

4. Rotstein, N.P., and Aveldaño, M.I. Synthesis of very long chain (up to 36 carbon) tetra, penta and hexaenoic fatty acids in retina. Biochem. J. 249(1), 191-200 (1988).

5. Ueno, S.-I., and Yonese, C. On the occurrence of new highly unsaturated fatty acids, C26H40O2 and C26H42O2, in tunny oil. J. Soc. Chem. Ind. 11(7), 437-442 (1936).

Reactions

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

unclassified Aurelia (#2623399)

Scyphozoa (#6142)

Occurrence of high levels of tetracosahexaenoic acid in the jellyfish Aurelia sp.,
Lipids, 2003

Pubmed ID: 14733367

String Representations

InChiKey (Click to copy)

YHGJECVSSKXFCJ-KUBAVDMBSA-N

InChi (Click to copy)

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-

SMILES (Click to copy)

C(CCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)(=O)O