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D2154

Sigma-Aldrich

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:
58688-54-3
Molecular Weight:
302.45
EC Number:
200-578-6
MDL number:
MFCD00065715
UNSPSC Code:
12352211
PubChem Substance ID:
24893642
NACRES:
NA.77

Quality Level

200

assay

≥98%

form

ethanol solution

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCCCC\C=C/C\C=C/C\C=C/CC#CCCCC(O)=O

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-

InChI key

GIOQWSLKUVKKAO-QNEBEIHSSA-N

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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

62.6 °F - closed cup

flash_point_c

17 °C - closed cup

Certificates of Analysis (COA)

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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
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
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)
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.
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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