(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID
- CAS NO.:88852-33-9
- Empirical Formula: C20H30O3
- Molecular Weight: 318.45
- MDL number: MFCD00216118
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 23:02:33
What is (+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID?
Description
(±)15-HEPE is a racemic mixture of the monohydroxy fatty acids 15(R)-HEPE and 15(S)-HEPE . 15(S)-HEPE is formed from EPA via a 15(S)-HpEPE intermediate, which is produced by 15-lipoxygenase (15-LO) and reduced by glutathione peroxidase (GPX).1,2 (±)15-HEPE is active against P. acnes and S. aureus (MICs = 128 and 512 mg/L, respectively).3 It inhibits aggregation of isolated rat neutrophils induced by the formyl peptide receptor agonist fMLP (IC50 = 4.7 μM).4 Bronchoalveolar lavage fluid (BALF) levels of (±)15-HEPE are increased in patients with allergic asthma or COVID-19.5,6
What are the applications of Application
(±)15-HEPE is a compound produced by non-enzymatic oxidation of EPA with equal amounts of 15(S) and 15(R)-HEPE
Definition
ChEBI: 15-HEPE is a hydroxyicosapentaenoic acid that consists of 5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid bearing an additional 15-hydroxy substituent. It has a role as a mouse metabolite. It is a HEPE and a hydroxy polyunsaturated fatty acid.
References
1. Miller, C., Yamaguchi, R.Y., and Ziboh, V.A. Guinea pig epidermis generates putative anti-
2. Tan, L., Xin, X., Zhai, L., et al. Drosophila fed ARA and EPA yields eicosanoids, 15S-
3. Desbois, A.P., and Lawlor, K.C. Antibacterial activity of long-
4. Lam, B., Marcinkiewicz, E., and Wong, P.Y.-K. Transformation of 15-
5. Lundstr?m, S.L., Yang, J., K?llberg, H.J., et al. Allergic asthmatics show divergent lipid mediator profiles from healthy controls both at baseline and following birch pollen provocation PLoS One 7(3),e33780(2012).
6. Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-
Properties of (+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID
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 |
pka | 4.75±0.10(Predicted) |
Safety information for (+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID
Computed Descriptors for (+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID
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