| Identification | Back Directory | [Name]
(+/-)-18-HYDROXY-5Z,8Z,11Z,14Z,16E-EICOSAPENTAENOIC ACID | [CAS]
141110-17-0 | [Synonyms]
(+/-)18-HEPE
LRWYBGFSVUBWMO-UXNZXXPISA-N
Eicosapentaenoic Acid Impurity 11
(+/-)-18-HYDROXY-5Z,8Z,11Z,14Z,16E-EICOSAPENTAENOIC ACID
(+/-)-18-HYDROXY-5Z,8Z,11Z,14Z,16E-EICOSAPENTAENOIC ACID
(5Z,8Z,11Z,14Z,16E)-18-Hydroxyicosa-5,8,11,14,16-pentaenoic acid
5,8,11,14,16-Eicosapentaenoic acid, 18-hydroxy-, (5Z,8Z,11Z,14Z,16E)- | [Molecular Formula]
C20H30O3 | [MDL Number]
MFCD03412012 | [MOL File]
141110-17-0.mol | [Molecular Weight]
318.45 |
| Chemical Properties | Back Directory | [Boiling point ]
488.0±45.0 °C(Predicted) | [density ]
0.997±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
0.1 M Na2CO3: 2 mg/ml; DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS (pH 7.2): 0.8 mg/ml | [form ]
Liquid | [pka]
4.75±0.10(Predicted) | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [Description]
(±)18-HEPE is produced by non-enzymatic oxidation of eicosapentaenoic acid (EPA; Item Nos. 90110 | 90110.1 | 21908). 18-HEPE levels are increased in the plasma and heart, as well as in the supernatant of cultured peritoneal macrophages isolated from fat-1 transgenic mice that are capable of endogenously producing ω-3 fatty acids from ω-6 fatty acids. It reduces increases in cardiac fibrosis and the expression of Nppa, Col1a1, Tgfb1, Cx3cl1, and Adgre1 induced by transverse aortic constriction in a mouse model of cardiac hypertrophy when administered at doses of 1 and 5 μg. | [Uses]
18-Hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoic Acid is produced by non-enzymatic oxidation of Eicosapentaenoic Acid (E477800). | [Definition]
ChEBI: 18-HEPE is a hydroxyicosapentaenoic acid that consists of 5Z,8Z,11Z,14Z,16E-icosapentaenoic acid with the hydroxy group located at position 18. It has a role as a human xenobiotic metabolite. It is a conjugate acid of a 18-HEPE(1-). | [References]
[1] TOSHIHARU ONODERA. Eicosapentaenoic acid and 5-HEPE enhance macrophage-mediated Treg induction in mice.[J]. Scientific Reports, 2017: 4560. DOI: 10.1038/s41598-017-04474-2
[2] JIEPING LI. An omega-3 polyunsaturated fatty acid derivative, 18-HEPE, protects against CXCR4-associated melanoma metastasis.[J]. Carcinogenesis, 2018, 39 11: 1380-1388. DOI: 10.1093/carcin/bgy117
[3] JIN ENDO. 18-HEPE, an n-3 fatty acid metabolite released by macrophages, prevents pressure overload-induced maladaptive cardiac remodeling.[J]. Journal of Experimental Medicine, 2014: 1673-1687. DOI: 10.1084/jem.20132011
[4] KANG J X. Fat-1 transgenic mice: A new model for omega-3 research[J]. Prostaglandins, leukotrienes, and essential fatty acids, 2007, 77 5: Pages 263-267. DOI: 10.1016/j.plefa.2007.10.010 |
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