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Chemical Compound Review:

Gaidic acid (E)-hexadec-2-enoic acid

Synonyms: CHEBI:37252, HMDB10735, LMFA01030054, AKOS015839097, FT-0632664, ...

Poe, N.D. et al., van der Wall, E.E. et al., Käkelä, R. et al., Takigawa, H. et al., Henderson, R.J. et al., et al.

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Disease relevance of Hexadecenoic acid

In acute and chronic infarction, similar distribution patterns are found for hexadecenoic acid and 43K, which indicates that hexadecenoic acid is a suitable substitute for the potassium analogs now in use for myocardial imaging [1].
The hexadecenoic acid of B. pertussis was in the cis-9 form [2].
Besides confirming our earlier observations, the present study tests the potential of 123I-FFA, hexadecenoic acid (123I-16-ha), and heptadecanoic acid (123I-17-H degree A), in assessing regional myocardial metabolism in 30 patients within a week of proven myocardial infarction [3].
Effect of growth temperature on the positional distribution of eicosapentaenoic acid and trans hexadecenoic acid in the phospholipids of a Vibrio species of bacterium [4].
Deficient production of hexadecenoic acid in the skin is associated in part with the vulnerability of atopic dermatitis patients to colonization by Staphylococcus aureus [5].

High impact information on Hexadecenoic acid

delta 6 Hexadecenoic acid (16:1 delta 6) composes more than 80% of the seed oil of Thunbergia alata [6].
Conversion of hexadecanoic acid to hexadecenoic acid by rat Delta 6-desaturase [7].
After intravenous injection in experimental animals, the clearance half-times of hexadecenoic acid for blood and myocardium are 1.7 and 20 min, respectively [1].
However, it has an unusually high content of hexadecenoic acid, a fatty acid not common in the major erythrocyte phospholipids [8].
Hexadecenoic acid, terminally labeled with 123I, partially overcomes these limitations by providing a compound that concentrates in the myocardium in proportion to relative regional blood flow and carries a gamma-emitter with desirable detection and imaging qualities [1].

Anatomical context of Hexadecenoic acid

1. Adipose tissues associated with the mystacial and superciliary vibrissae of the Saimaa seal (Phoca hispida saimensis) contained 31% of hexadecenoic acid (16:1 omega 7), which was almost twice the already high amount in blubber [9].

References

Experimental basis of myocardial imaging with 123I-labeled hexadecenoic acid. Poe, N.D., Robinson, G.D., Graham, L.S., MacDonald, N.S. J. Nucl. Med. (1976) [Pubmed]
Characteristic lipids of Bordetella pertussis: simple fatty acid composition, hydroxy fatty acids, and an ornithine-containing lipid. Kawai, Y., Moribayashi, A. J. Bacteriol. (1982) [Pubmed]
Dynamic myocardial scintigraphy with 123I-labeled free fatty acids in patients with myocardial infarction. van der Wall, E.E., den Hollander, W., Heidendal, G.A., Westera, G., Majid, P.A., Roos, J.P. European journal of nuclear medicine. (1981) [Pubmed]
Effect of growth temperature on the positional distribution of eicosapentaenoic acid and trans hexadecenoic acid in the phospholipids of a Vibrio species of bacterium. Henderson, R.J., Millar, R.M., Sargent, J.R. Lipids (1995) [Pubmed]
Deficient production of hexadecenoic acid in the skin is associated in part with the vulnerability of atopic dermatitis patients to colonization by Staphylococcus aureus. Takigawa, H., Nakagawa, H., Kuzukawa, M., Mori, H., Imokawa, G. Dermatology (Basel) (2005) [Pubmed]
delta 6 Hexadecenoic acid is synthesized by the activity of a soluble delta 6 palmitoyl-acyl carrier protein desaturase in Thunbergia alata endosperm. Cahoon, E.B., Cranmer, A.M., Shanklin, J., Ohlrogge, J.B. J. Biol. Chem. (1994) [Pubmed]
Conversion of hexadecanoic acid to hexadecenoic acid by rat Delta 6-desaturase. Guillou, H., Rioux, V., Catheline, D., Thibault, J.N., Bouriel, M., Jan, S., D'Andrea, S., Legrand, P. J. Lipid Res. (2003) [Pubmed]
Production of 1,2-diacylglycerol and phosphatidate in human erythrocytes treated with calcium ions and ionophore A23187. Allan, D., Watts, R., Michell, R.H. Biochem. J. (1976) [Pubmed]
Fatty acid composition of fats around the mystacial and superciliary vibrissae differs from that of blubber in the Saimaa ringed seal (Phoca hispida saimensis). Käkelä, R., Hyvärinen, H. Comp. Biochem. Physiol., B (1993) [Pubmed]

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