D2154

5,6-Dehydroarachidonic acid

Name: 5,6-Dehydroarachidonic acid
Brand: SIGMA
Price: 369 EUR

≥98%, ethanol solution

Synonym(e):

5,6-dehydro AA, cis-8,11,14-Eicosatrien-5-ynoic acid

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100 μG

€ 369,00

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Über diesen Artikel

Empirische Formel (Hill-System):

C₂₀H₃₀O₂

CAS-Nummer:

58688-54-3

Molekulargewicht:

302.45

NACRES:

NA.77

PubChem Substance ID:

24893642

UNSPSC Code:

12352211

EC Number:

200-578-6

MDL number:

MFCD00065715

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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

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Dieser Artikel	900411E	181198	735000
Sigma-Aldrich D2154 5,6-Dehydroarachidonic acid	Avanti 900411E arachidonic acid-alkyne	Sigma-Aldrich 181198 Arachidonic Acid	Sigma-Aldrich 735000 Arachidonic-5,6,8,9,11,12,14,15-d₈ acid
assay ≥98%	assay -	assay ≥99% (TLC and GC)	assay ≥98% (CP)
storage temp. −20°C	storage temp. −20°C	storage temp. −70°C	storage temp. −20°C
form ethanol solution	form ethanol solution	form oil	form liquid
shipped in wet ice	shipped in dry ice	shipped in dry ice	shipped in dry ice
Quality Level 200	Quality Level -	Quality Level 100	Quality Level 200

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 K_i for the conversion of arachidonic acid to 5-HPETE is 15 μM.

pictograms

GHS02,GHS07

signalword

Danger

hcodes

H225,H319

pcodes

P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Lagerklasse

3 - Flammable liquids

wgk

WGK 2

flash_point_f

62.6 °F - closed cup

flash_point_c

17 °C - closed cup

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Synthesis of [5,6-3H]arachidonic acid and its use in development of a sensitive assay for prostacyclin synthetase.

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)

Mediation of neurogenic ion transport by acetylcholine, prostanoids and 5-hydroxytryptamine in porcine ileum.

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.

An analysis of the relationship between 5-lipoxygenase product generation and the secretion of preformed mediators from mouse bone marrow-derived mast cells.

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

[Synthesis of (8Z,11Z,14Z)-eicosatrien-5-ynoic (5,6-dehydroarachidonic) acid and its transformation into [5,6-3H]arachidonic acid and [5,6-3H]prostaglandins E2 and F2 alpha].

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.

Global Trade Item Number

SKU	GTIN
D2154-25UG	04061838070678
D2154-100UG	04061837896828

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