H1142
15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid
~150 μg/mL in ethanol, ≥97.0% (HPLC)
Synonym(s):
(15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoic acid, (S)-15-HETE, 15(S)-HETE
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About This Item
Empirical Formula (Hill Notation):
C20H32O3
CAS Number:
Molecular Weight:
320.47
PubChem Substance ID:
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
2470466
MDL number:
assay
≥97.0% (HPLC)
concentration
~150 μg/mL in ethanol
shipped in
dry ice
storage temp.
−20°C
SMILES string
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
InChI key
JSFATNQSLKRBCI-VAEKSGALSA-N
Biochem/physiol Actions
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.
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
57.2 °F - closed cup
flash_point_c
14 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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Eicosanoids in inflammatory skin diseases.
K Fogh et al.
Prostaglandins & other lipid mediators, 63(1-2), 43-54 (2000-12-05)
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)