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Merck

L0521

Lipoxin A4

ethanol solution

Synonym(s):

(5S,6R,15S)-Trihydroxy-(7E,9E,11Z,13E)-Eicosatetraenoic acid

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About This Item

Empirical Formula (Hill Notation):
C20H32O5
CAS Number:
89663-86-5
Molecular Weight:
352.47
NACRES:
NA.77
PubChem Substance ID:
24896257
UNSPSC Code:
12352211
EC Number:
200-578-6
MDL number:
MFCD00065845

Key Documents

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Product Name

Lipoxin A4, ethanol solution

InChI key

IXAQOQZEOGMIQS-SSQFXEBMSA-N

InChI

1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1

SMILES string

CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O

form

ethanol solution

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

Biochem/physiol Actions

Lipoxin A4 (LXA4) is synthesized from arachidonic acid and is an endogenous lipoxygenase-derived eicosanoid mediator. It is a potent human protein kinase C activator. It inhibits cytotoxicity of natural killer cells. LXA4 regulates the immune system and inflammation. In the brain, it modulates neuronal signaling and slow wave sleep. LXA4 binds to cannabinoid receptors. LXA4 plays a key role in the maintenance of endometrium and reproductive function. Depletion of LXA4 contributes to the pathophysiology of cystic fibrosis (CF).

Packaging

Packaged under argon.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

55.4 °F

flash_point_c

13 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SLCQ7104
SLCN6184
SLBT7048
SLBS9136
SLBR3625V

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Ioannis Kourtzelis et al.
Nature immunology, 20(1), 40-49 (2018-11-21)
Resolution of inflammation is essential for tissue homeostasis and represents a promising approach to inflammatory disorders. Here we found that developmental endothelial locus-1 (DEL-1), a secreted protein that inhibits leukocyte-endothelial adhesion and inflammation initiation, also functions as a non-redundant downstream
The lipoxin receptor ALX: potent ligand-specific and stereoselective actions in vivo.
Chiang N, et al.
Pharmacological Reviews, 58(3), 463-487 (2006)
Romain A Colas et al.
Infection and immunity, 86(4) (2018-01-24)
Trypanosoma cruzi is a protozoan parasite that causes Chagas disease (CD). CD is a persistent, lifelong infection affecting many organs, most notably the heart, where it may result in acute myocarditis and chronic cardiomyopathy. The pathological features include myocardial inflammation
Lipoxin A4 and its analog suppress inflammation by modulating HMGB1 translocation and expression in psoriasis.
Liu X, et al.
Scientific Reports, 7(1), 7100-7100 (2017)
Stephanie G Dakin et al.
Scientific reports, 7(1), 11009-11009 (2017-09-10)
The mechanisms underpinning the failure of inflammation to resolve in diseased musculoskeletal soft tissues are unknown. Herein, we studied bioactive lipid mediator (LM) profiles of tendon-derived stromal cells isolated from healthy donors and patients with chronic tendinopathy. Interleukin(IL)-1β treatment markedly
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