9,12-OCTADECADIYNOIC ACID
Synonym(s):ODYA;Ro 3-1314
- CAS NO.:2012-14-8
- Empirical Formula: C18H28O2
- Molecular Weight: 276.41
- MDL number: MFCD00797685
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-07-02 08:55:16
What is 9,12-OCTADECADIYNOIC ACID?
What are the applications of Application
9,12-Octadecadiynoic Acid is an inhibitor of Cox and LO
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.
Properties of 9,12-OCTADECADIYNOIC ACID
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 information for 9,12-OCTADECADIYNOIC ACID
Computed Descriptors for 9,12-OCTADECADIYNOIC ACID
New Products
4-Aminotetrahydropyran-4-carbonitrile Hydrochloride (R)-3-Aminobutanenitrile Hydrochloride 4-AMINO-TETRAHYDRO-PYRAN-4-CARBOXYLIC ACID HCL 4-(Dimethylamino)tetrahydro-2H-pyran-4-carbonitrile 3-((Dimethylamino)methyl)-5-methylhexan-2-one oxalate 1,4-Dioxa-8-azaspiro[4.5]decane 5-Bromo-2-nitropyridine Nimesulide BP Aceclofenac IP/BP/EP Mefenamic Acid IP/BP/EP/USP Diclofenac Sodium IP/BP/EP/USP Ornidazole IP Diclofenac Potassium SODIUM AAS SOLUTION ZINC AAS SOLUTION BUFFER SOLUTION PH 10.0(BORATE) GOOCH CRUCIBLE SINTERED AQUANIL 5 BERYLLIUM AAS SOLUTION 2-Bromo-1-(bromomethyl)-3-chloro-5-nitrobenzene 2-Bromo-3-nitroaniline N-(3-Hydroxypropyl)-N-methylacetamide 3-Bromo-6-chloropyridazine 4-ethyl-3-nitrobenzoic acidRelated products of tetrahydrofuran
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