(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID Property

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

(+/-)-15-HYDROXY-5Z,8Z,11Z,13E,17Z-EICOSAPENTAENOIC ACID Chemical Properties,Usage,Production

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

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-inflammatory metabolites from fish oil polyunsaturated fatty acids Lipids 24(12),998-1003(1989).
2. Tan, L., Xin, X., Zhai, L., et al. Drosophila fed ARA and EPA yields eicosanoids, 15S-hydroxy-5Z,8Z, 11Z, 13E-eicosatetraenoic acid, and 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid Lipids 51(4),435-449(2016).
3. Desbois, A.P., and Lawlor, K.C. Antibacterial activity of long-chain polyunsaturated fatty acids against Propionibacterium acnes and Staphylococcus aureus Mar. Drugs 11(11),4544-4557(2013).
4. Lam, B., Marcinkiewicz, E., and Wong, P.Y.-K. Transformation of 15-hydroperoxyeicosapentaenoic acid into mono- and dihydroxyeicosapentaenoic acids by human platelets Drugs affecting leukotrienes and other eicosanoid pathways ,167-180(1985).
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-19 patients FASEB J. 35(6),e21666(2021).