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H1142

Sigma-Aldrich

15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid

~150 μg/mL in ethanol, ≥97.0% (HPLC)

Synonyme(s) :

(15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoic acid, (S)-15-HETE, 15(S)-HETE

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About This Item

Formule empirique (notation de Hill):
C20H32O3
Numéro CAS:
54845-95-3
Poids moléculaire :
320.47
Numéro Beilstein :
2470466
Numéro MDL:
MFCD00063590
Code UNSPSC :
12352200
ID de substance PubChem :
24895431

Pureté

≥97.0% (HPLC)

Concentration

~150 μg/mL in ethanol

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

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

InChI

1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1

Clé InChI

JSFATNQSLKRBCI-VAEKSGALSA-N

Actions biochimiques/physiologiques

Metabolite of arachidonic acid via the 15-lipoxygenase pathway that may be involved in pulmonary anti-inflammatory responses through the inhibition of 5-lipoxygenase. 15(S)-HETE suppresses the incorporation of thymidine and biosynthesis of prostaglandin E2 in tumor cell cultures. Treatment of colon cancer cells with 15(S)-HETE inhibited cell proliferation and induced apoptosis, which was preceded by an increase in TGF-beta-inducible early gene (TIEG) and a decrease in Bcl-2.

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Danger

Mentions de danger

H225,H315,H319,H335

Classification des risques

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

57.2 °F - closed cup

Point d'éclair (°C)

14 °C - closed cup

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

M Profita et al.
American journal of physiology. Cell physiology, 279(4), C1249-C1258 (2000-09-26)
We evaluated the levels of 15(S)-hydroxyeicosatetraenoic acid [15(S)-HETE] and the expression of 15-lipoxygenase (15-LO) mRNA in induced sputum obtained from 10 control and 15 chronic bronchitis subjects. 15(S)-HETE was evaluated by reverse phase high-performance liquid chromatography separation followed by specific
M Profita et al.
American journal of respiratory cell and molecular biology, 20(1), 61-68 (1998-12-31)
15(S)-Hydroxyeicosatetraenoic acid (15[S]-HETE) is a 15-lipoxygenase (15-LO) metabolite that may play an important role in different pulmonary diseases. 15-HETE is synthesized by different epithelial cells and may be subsequently incorporated into cellular phospholipids. We studied the role of interleukin-4 (IL-4)
Eicosanoids in inflammatory skin diseases.
K Fogh et al.
Prostaglandins & other lipid mediators, 63(1-2), 43-54 (2000-12-05)
Li-Xing Tian et al.
Cellular immunology, 349, 104047-104047 (2020-02-06)
The polarization of macrophages is critical to inflammation and tissue repair, with unbalanced macrophage polarization associated with critical dysfunctions of the immune system. Cytochrome P450 1A1 (CYP1A1) is a hydroxylase mainly controlled by the inflammation-limiting aryl hydrocarbon receptor (AhR), which
Cui Ma et al.
Hypertension (Dallas, Tex. : 1979), 58(4), 679-688 (2011-08-24)
We have found that 15-hydroxyeicosatetraenoic acid (15-HETE) induced by hypoxia was an important mediator in the regulation of hypoxic pulmonary hypertension, including the pulmonary vasoconstriction and remodeling. However, the underlying mechanisms of the remodeling induced by 15-HETE are poorly understood.
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