2012-14-8 Usage
Biological Activity
ki: 0.6 μm for ram seminal vesicle cox9,12-octadecadiynoic acid is a cox and lipoxygenase inhibitor.cyclooxygenase (cox) is an enzyme responsible for the formation of prostanoids, such as thromboxane and prostaglandins. pharmaceutical inhibition of cox can lead to relief from the symptoms of inflammation and pain. nonsteroidal anti-inflammatory drugs, including aspirin and ibuprofen, display their effects via inhibition of cox.
Biochem/physiol Actions
Potent cyclooxygenase and lipoxygenase inhibitor.
in vitro
9,12-octadecadiynoic acid was identified as an inhibitor of both cox and lipoxygenase, which could inhibit ram seminal vesicle cox. 9,12-octadecadiynoic acid was found to be a more effective inhibitor of cox-1 than of 15-lo when used at a concentration of 48 μm [1,2]. in another study, fatty acids from natural sources including 9,12-octadecadiynoic acid were isolated and assayed for their effect on the bioconversion of arachidonic acid into prostaglandin e2. two very active cyclooxygenase inhibitors were discovered, namely jacarandic acid and the synthetic 8z, 10e, 12e-octadecatrienoic acid. earlier described potent inhibitors showed the following ic50 values: 1.3 μm for indomethacin; 1.3 μm for 9,12-octadecadiynoic acid, 2.7 μm for 8z, 12e, 14z-eicosatrienoic acid; 4.4 μm for 5,8,11,14-eicosatetraynoic acid [3].
references
[1] vanderhoek, j. y. and lands, w.e.m. acetylenic inhibitors of sheep vesicular gland oxygenase. biochimica et biophysica acta 296, 374-381 (1973).[2] downing, d. t.,barve, j.a.,gunstone, f.d., et al. structural requirements of acetylenic fatty acids for inhibition of soybean lipoxygenase and prostaglandin synthase. biochimica et biophysica acta 280, 343-347 (1972).[3] nugteren dh, christ-hazelhof e. naturally occurring conjugated octadecatrienoic acids are strong inhibitors of prostaglandin biosynthesis. prostaglandins. 1987 mar;33(3):403-17.
Check Digit Verification of cas no
The CAS Registry Mumber 2012-14-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,1 and 2 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2012-14:
(6*2)+(5*0)+(4*1)+(3*2)+(2*1)+(1*4)=28
28 % 10 = 8
So 2012-14-8 is a valid CAS Registry Number.
InChI:InChI=1/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-5,8,11-17H2,1H3,(H,19,20)
2012-14-8Relevant articles and documents
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Raphael,Sondheimer
, p. 2100 (1950)
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The Biosynthesis of Calendic Acid, Octadeca-(8E,10E,12Z)-trienoic Acid, by Developing Marigold Seeds: Origins of (E,E,Z) and (Z,E,Z) conjugated Triene Acids in Higher Plants
Crombie, Leslie,Holloway, Stephen J.
, p. 2425 - 2434 (2007/10/02)
Using an homogenate of marigold seeds, gathered 15 days after flower-drop, linoleic acid and oleic acid were incorporated into calendic acid with little randomisation of the label. Linolenic acid was not incorporated.Despite requiring 12,13-dehydrogenation to form linoleic acid, the putative precursor, oleic acid was better incorporated than administered linoleic acid.Stearic acid, requiring both 12,13- and 9,10-dehydrogenation, was a poor precursor.The results of a series of doublelabelling experiments support and supplement these conclusions. Octadec-9-enoic acid was synthesised and employed in a mass-spectral experiment to show that conversion into calendic acid involves loss of two deuterium and two hydrogen atoms (deuterium at C-16 and C-17 was introduced for loading purposes only, in order to increase the sensitivity of the experiment).Taken with -labelling work, the experiment indicates that during conversion of linoleic acid into calendic acid, there is no loss of the labelled hydrogens at C-9, -10, -12, or -13, but loss of hydrogen from each of C-8 and C-11. (9S)-Hydroxyoctadeca-(10E,12Z)-dienoic acid (α-dimorphecolic acid) was isolated and converted into (R/S)-hydroxy- and hydroperoxy-octadeca-(10E,12Z)-dienoic acids.Neither labelled specimen was converted into calendic acid by marigold seed homogenate.Abstraction of a hydrogen atom from C-11 of linoleic acid is viewed as giving an (E)-allylic radical which, as in lipoxygenase reactions, can be trapped by oxygen at C-9, thus providing a source of α-dimorphecolic acid, a minor component of marigold seed oil.However, this hydroxyacid is apparently a terminus rather than an intermediate for calendic acid.Formation of the latter seems best accounted for by formal loss of a hydrogen atom from C-8 of the (E)-allylic redical.The general position relating to the formation of (E,E,Z) and (Z,E,Z)-trienes is summarised.
