88852-33-9
Chemical Structure
(±)15-HEPE
Synonym(s): (±)15-hydroxyeicosapentaenoic acid; 15-OHEPA
- CAS No.: 88852-33-9
- Formula:C20H30O3
- Molecular Weight:318.45
IUPAC Name: (5Z,8Z,11Z,13E,17Z)-15-hydroxyicosa-5,8,11,13,17-pentaenoic acid
InChIKey: WLKCSMCLEKGITB-XWJJKCKWSA-N
SMILES: CC/C=C\CC(O)/C=C/C=C\C/C=C\C/C=C\CCCC(O)=O
Biological Activity: (±)15-HEPE ((±)15-hydroxyeicosapentaenoic acid; 15-OHEPA) is a racemic mixture of monohydroxy fatty acids, including 15(R)-HEPE and 15(S)-HEPE (HY-130675A). (±)15-HEPE exhibits anti-inflammatory, anti-allergic, and antibacterial activities. (±)15-HEPE rapidly kills S. aureus and inhibits the growth of P. acnes, but has no bactericidal effect. (±)15-HEPE is a PPARγ agonist that inhibits mast cell degranulation. (±)15-HEPE is also a 5-lipoxygenase inhibitor with an IC50 of 28 μM, reducing the production of pro-inflammatory leukotrienes. (±)15-HEPE can be used for research on acne vulgaris, allergic rhinitis, and psoriasis[1][2][3][4][5].
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(±)15-HEPE | (±)15-HEPE ((±)15-hydroxyeicosapentaenoic acid; 15-OHEPA) is a racemic mixture of monohydroxy fatty acids, including 15(R)-HEPE and 15(S)-HEPE (HY-130675A). (±)15-HEPE exhibits anti-inflammatory, anti-allergic, and antibacterial activities. (±)15-HEPE rapidly kills S. aureus and inhibits the growth of P. acnes, but has no bactericidal effect. (±)15-HEPE is a PPARγ agonist that inhibits mast cell degranulation. (±)15-HEPE is also a 5-lipoxygenase inhibitor with an IC50 of 28 μM, reducing the production of pro-inflammatory leukotrienes. (±)15-HEPE can be used for research on acne vulgaris, allergic rhinitis, and psoriasis. | |||||||||||||||||||||
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References
- [1]. Desbois AP, et al. Antibacterial activity of long-chain polyunsaturated fatty acids against Propionibacterium acnes and Staphylococcus aureus. Marine drugs. 2013 Nov 13;11(11):4544-57. [Content Brief]
- [2]. Sawane K, et al. Dietary Omega-3 Fatty Acid Dampens Allergic Rhinitis via Eosinophilic Production of the Anti-Allergic Lipid Mediator 15-Hydroxyeicosapentaenoic Acid in Mice. Nutrients. 2019 Nov 22;11(12):2868. [Content Brief]
- [3]. Ziboh VA, et al. Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites. Am J Clin Nutr. 2000 Jan;71(1 Suppl):361S-6S. [Content Brief]
- [4]. Miller C, et al. Guinea pig epidermis generates putative anti-inflammatory metabolites from fish oil polyunsaturated fatty acids. Lipids. 1989 Dec;24(12):998-1003. [Content Brief]
- [5]. Wang D, et al. Quantitative profiling of differentially produced oxylipins in human adipose derived mesenchymal stem cells under proinflammatory stimulation [Preprint]. Research Square. 2021 Jan 19.
