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H6643

(+)-5(S)-Hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acid

Name: (+)-5(S)-Hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acid
Brand: SIGMA

~75 μg/mL in ethanol, ~98%

Synonyme(s) :

(+)-5-HETE, 5(S)-HETE

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About This Item

Formule empirique (notation de Hill):

C₂₀H₃₂O₃

Numéro CAS:

70608-72-9

Poids moléculaire :

320.47

Numéro MDL:

MFCD00065820

Code UNSPSC :

12352211

ID de substance PubChem :

24895753

Pureté

~98%

Concentration

~75 μg/mL in ethanol

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES

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

Actions biochimiques/physiologiques

A substrate for hydroxyeicosanoid dehydrogenase in polymorphonuclear (PMN) leucocytes, where it is converted to 5-oxo-ETE. Both compounds are reported to increase the intracellular mobilization of calcium in PMN leucocytes.

Pictogrammes

GHS02,GHS07

Mention d'avertissement

Danger

Mentions de danger

H225,H319

Conseils de prudence

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

Classification des risques

Eye Irrit. 2 - Flam. Liq. 2

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

57.2 °F

Point d'éclair (°C)

14 °C

Équipement de protection individuelle

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

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Consulter la Bibliothèque de documents

Esterified eicosanoids are acutely generated by 5-lipoxygenase in primary human neutrophils and in human and murine infection.

Stephen R Clark et al.

Blood, 117(6), 2033-2043 (2010-12-24)

5-Lipoxygenase (5-LOX) plays key roles in infection and allergic responses. Herein, four 5-LOX-derived lipids comprising 5-hydroxyeicosatetraenoic acid (HETE) attached to phospholipids (PLs), either phosphatidylethanolamine (PE) or phosphatidylcholine (18:0p/5-HETE-PE, 18:1p/5-HETE-PE, 16:0p/5-HETE-PE, and 16:0a/5-HETE-PC), were identified in primary human neutrophils. They formed

Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes.

W S Powell et al.

The Journal of biological chemistry, 267(27), 19233-19241 (1992-09-25)

Human polymorphonuclear leukocytes (PMNL) convert 6-trans isomers of leukotriene B4 (LTB4) to dihydro metabolites (Powell, W.S., and Gravelle, F. (1988) J. Biol. Chem. 263, 2170-2177). In the present study we investigated the mechanism for the initial step in the formation

Substrate selectivity of 5-hydroxyeicosanoid dehydrogenase and its inhibition by 5-hydroxy-Delta6-long-chain fatty acids.

Pranav Patel et al.

The Journal of pharmacology and experimental therapeutics, 329(1), 335-341 (2009-01-24)

5-Oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-oxo-ETE) is a metabolite of the 5-lipoxygenase (5-LO) product 5S-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-HETE), formed by the microsomal enzyme 5-hydroxyeicosanoid dehydrogenase (5-HEDH). 5-oxo-ETE is a chemoattractant for neutrophils and eosinophils, both in vitro and in vivo. To examine the substrate

Vitamin E modulates the lipoxygenation of arachidonic acid in leukocytes.

E J Goetzl

Nature, 288(5787), 183-185 (1980-11-13)

The arachidonic acid released from cellular phospholipids of specifically stimulated platelets and leukocytes is oxygenated enzymatically by two major pathways. A complex cycloxygenase converts some of the free arachidonic acid to labile endoperoxides that are transformed to prostaglandins, thromboxanes and

Celecoxib inhibits 5-lipoxygenase.

Thorsten J Maier et al.

Biochemical pharmacology, 76(7), 862-872 (2008-08-12)

Celecoxib is a selective cyclooxygenase-2 (COX-2) inhibitor used in the therapy of inflammatory and painful conditions. Various COX-2-independent pharmacological effects, such as a chemo-preventive and tumor-regressive activity have been suggested, but the respective non-COX-2 targets of celecoxib are still a

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