6,9,12,15,18,21-Tetracosahexaenoic acid
IUPAC 名称
(6E,9E,12E,15E,18E,21E)-tetracosa-6,9,12,15,18,21-hexaenoate
描述
6,9,12,15,18,21-Tetracosahexaenoic acid (24:6n-3) is one of the n-3 PUFA and is a very long chain fatty acid. Distribution of 24:6n-3 in marine organisms was investigated by several researchers. Takagi et al. reported relatively high
contents of 24:6n-3 in sea lilies and brittle stars (4?10% of total fatty acids). High 24:6n-3 content was also found in marine coelenterates. In some edible fishes, 24:6n-3 was detected at significant levels (0?10% of total fatty acids).The existence of 24:6n-3 in mammalian tissues was reported with other very long chain fatty acids in the spermatozoa,the retina, and the brain. Voss et al.reported that 24:6n-3 is formed as an intermediate in the metabolic pathway from 20:5n-3 to 22:6n-3 in rat liver.Even though 24:6n-3 is a PUFA existing in fish and mammalian species, physiological functions of 24:6n-3 have not been studied. As functions to be studied, anti-inflammatory and antiallergic
effects of 24:6n-3 are noteworthy because these events are known to be closely related to the unsaturated fatty acid metabolism such as in the arachidonic acid cascade, and 20:5n-3 and 22:6n-3 were reported to suppress inflammatory actions by influencing arachidonic acid metabolism
24:6n-3 could inhibit the antigen-stimulated production of LT-related compounds as well as other n-3 polyunsaturated fatty acids (PUFA) such as eicosapentaenoic
acid (20:5n-3) and docosahexaenoic acid (22:6n-3), which are major n-3 PUFA in fish oils; 24:6n-3 was also shown to reduce the histamine content in MC/9 cells at 25 uM (27% reduction from the control), and the effect was diminished with increase of the fatty acid concentration (up to 100 uM). These two n-3 PUFA, 20:5n-3 and 22:6n-3, also reduced the histamine content (16 and 20% reduction at 25 μM, respectively), whereas arachidonic acid (20:4n-6) increased it (18% increase at 25 μM). [HMDB]
异构
CC\C=C\C\C=C\C\C=C\C\C=C\C\C=C\C\C=C\CCCCC([O-])=O
InChI标识符
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)/p-1/b4-3+,7-6+,10-9+,13-12+,16-15+,19-18+
键
YHGJECVSSKXFCJ-SFGLVEFQSA-M