D2154
5,6-Dehydroarachidonic acid
≥98%, ethanol solution
Synonym(s):
5,6-dehydro AA, cis-8,11,14-Eicosatrien-5-ynoic acid
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About This Item
Empirical Formula (Hill Notation):
C20H30O2
CAS Number:
Molecular Weight:
302.45
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
EC Number:
200-578-6
MDL number:
InChI key
GIOQWSLKUVKKAO-QNEBEIHSSA-N
InChI
1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
SMILES string
CCCCC\C=C/C\C=C/C\C=C/CC#CCCCC(O)=O
assay
≥98%
form
ethanol solution
shipped in
wet ice
storage temp.
−20°C
Quality Level
Related Categories
General description
An analog of arachidonic acid in which the 5,6 double bond has been replaced with an acetylene group.
Biochem/physiol Actions
Inhibits 5-lipoxygenase of guinea pig leukocytes with an IC50 of 10 μM. In extracts of rat basophilic leukemia cells preincubated with 5,6-dehydro AA, the Ki for the conversion of arachidonic acid to 5-HPETE is 15 μM.
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2
Storage Class
3 - Flammable liquids
wgk
WGK 2
flash_point_f
62.6 °F - closed cup
flash_point_c
17 °C - closed cup
Regulatory Information
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G I Miagkova et al.
Bioorganicheskaia khimiia, 13(3), 415-419 (1987-03-01)
8Z,11Z,14Z-Eicosatriene-5-ynoic acid and its tritium-labelled analogue, [5,6-3H]arachidonic acid, have been synthesized on the basis of acetylenic compounds. [5,6-3H]Arachidonic acid has been used as substrate for the enzymatic synthesis of [5,6-3H]PGE2 and [5,6-3H]PGF2 alpha.
E Razin et al.
Journal of immunology (Baltimore, Md. : 1950), 133(2), 938-945 (1984-08-01)
The quantitative relationships between the secretion of a granule-associated mediator, beta-hexosaminidase, and the oxidative metabolism of arachidonic acid by the 5-lipoxygenase pathway were analyzed for a homogeneous population of T cell-dependent, bone marrow-derived, murine mast cells. The mast cells were
H H Tai et al.
Biochemistry, 19(9), 1989-1993 (1980-04-29)
[5,6-3H]arachidonic acid has been prepared by catalytic reduction of eicosa-cis-8,11,14-trien-5-ynoic acid (IV) over Lindlar catalyst. When either [5,6-3H]arachidonic acid or [5,6-3H]PGH2 is converted into PGI2 by swine aortic microsomes, the tritium at C-6 is lost to the medium. Thus, the
Strong suppression by mononuclear leukocytes from human newborns on maternal leukocytes: mediation by prostaglandins.
S A Johnsen et al.
Clinical immunology and immunopathology, 23(3), 606-615 (1982-06-01)
DeWayne Townsend et al.
European journal of pharmacology, 519(3), 285-289 (2005-09-02)
Enteric neural activity modulates active transepithelial ion transport in the intestine. We investigated the neural circuits mediating neurogenic secretion in mucosal explants from porcine ileum. Transmural electrical stimulation increased short-circuit current, a measure of active ion transport, by 35+/-2 microA/cm2.
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