9,12-OCTADECADIYNOIC ACID Property

Melting point:

42-43 °C(Solv: ligroine (8032-32-4))

Boiling point:

143-154 °C(Press: 0.005-0.01 Torr)

Density 

0.963±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

≤10mg/ml in ethanol;10mg/ml in DMSO;10mg/ml in methanol;10mg/ml in acetone;10mg/ml in acetonitrile

form 

crystalline solid

pka

4.77±0.10(Predicted)

color 

White to off-white

Safety

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

9,12-OCTADECADIYNOIC ACID Chemical Properties,Usage,Production

Definition

ChEBI: Octadeca-9,12-diynoic acid is an octadecadiynoic acid having its triple bonds at positions 9 and 12.

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.