(+/-)-18-HYDROXY-5Z,8Z,11Z,14Z,16E-EICOSAPENTAENOIC ACID

(+/-)-18-HYDROXY-5Z,8Z,11Z,14Z,16E-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

form 

Liquid

pka

4.75±0.10(Predicted)

color 

Colorless to light yellow

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

(+/-)-18-HYDROXY-5Z,8Z,11Z,14Z,16E-EICOSAPENTAENOIC ACID Chemical Properties,Usage,Production

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