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D2154

5,6-Dehydroarachidonic acid

Name: 5,6-Dehydroarachidonic acid
Brand: SIGMA

≥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

NACRES:

NA.77

PubChem Substance ID:

24893642

UNSPSC Code:

12352211

EC Number:

200-578-6

MDL number:

MFCD00065715

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Properties

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

Description

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

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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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)

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

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Global Trade Item Number

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