(+/-)9-HODE Chemical Properties

Boiling point:

416.1±33.0 °C(Predicted)

Density 

0.970±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 50 mg/ml; PBS pH 7.2: 1 mg/ml

form 

Clear to light-yellow liquid.

pka

4.78±0.10(Predicted)

(+/-)9-HODE Usage And Synthesis

Description

(±)9-HODE is one of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. Approximately equal proportions of both isomers are found in mitochondrial and plasma membranes of rabbit reticulocytes. Oxidized LDL contains significant amounts of esterified 9- and 13-HpODEs and HODEs.

Uses

(±)9-HODE is one of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. Approximately equal proportions of both isomers are found in mitochondrial and plasma membranes of rabbit reticulocytes. Oxidized LDL contains significant amounts of esterified 9- and 13-HpODEs and HODEs.

Uses

(+/-)9-HODE is a distinct product of non-enzymatic linoleic acid oxidation.Also, it is one of the component in rice koji extract (RKE), which activates peroxisome proliferator-activated receptor alpha (PPARα).It is derived from Methyl Linoleate (M265190), which is a common methyl ester produced from soybean or canola oil and methanol. Methyl Linoleate is classified as a biodiesel due to its long methyl chain and is used as a fuel in standard diesel engines.

Definition

ChEBI: 9-HODE is a HODE that consists of (10E,12Z)-octadecadienoic acid with the hydroxy substituent located at position 9. It has a role as a plant metabolite, a human metabolite and a mouse metabolite. It is a conjugate acid of a 9-HODE(1-).

References

[1] HARTMUT KüHN  Rainer W  Jutta BELKNER. Subcellular distribution of lipoxygenase products in rabbit reticulocyte membranes*[J]. The FEBS journal, 1990, 191 1: 221-227. DOI: 10.1111/j.1432-1033.1990.tb19113.x
[2] H KüHN  R W  J Belkner. Metabolism of polyenoic fatty acids by rabbit reticulocytes. Intracellular action of the erythroid lipoxygenase on membrane lipids.[J]. Biomedica biochimica acta, 1990, 49 2-3: S25-30.
[3] V A FOLCIK  M K C. Predominance of esterified hydroperoxy-linoleic acid in human monocyte-oxidized LDL.[J]. Journal of Lipid Research, 1994, 35 9: 1570-1582.
[4] G KU. Induction of interleukin 1 beta expression from human peripheral blood monocyte-derived macrophages by 9-hydroxyoctadecadienoic acid.[J]. The Journal of Biological Chemistry, 1992, 267 20: 14183-14188.
[5] JIE YANG. Aspirin prevents metastasis by limiting platelet TXA2 suppression of T cell immunity[J]. Nature, 2025, 640 8060: 1052-1061. DOI: 10.1038/s41586-025-08626-7
[6] JAMIE L LAHVIC. Specific oxylipins enhance vertebrate hematopoiesis via the receptor GPR132.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2018, 115 37: 9252-9257. DOI: 10.1073/pnas.1806077115
[7] KATHARINA KERN. The G2A Receptor Controls Polarization of Macrophage by Determining Their Localization Within the Inflamed Tissue.[J]. Frontiers in Immunology, 2018: 2261. DOI: 10.3389/fimmu.2018.02261
[8] SANDRA GOUVEIA-FIGUEIRA. Characterisation of (R)-2-(2-Fluorobiphenyl-4-yl)-N-(3-Methylpyridin-2-yl)Propanamide as a Dual Fatty Acid Amide Hydrolase: Cyclooxygenase Inhibitor.[J]. PLoS ONE, 2015: e0139212. DOI: 10.1371/journal.pone.0139212
[9] ALWENA H MORGAN. Quantitative assays for esterified oxylipins generated by immune cells[J]. Nature Protocols, 2010, 5 12: 1919-1931. DOI: 10.1038/nprot.2010.162

(+/-)9-HODE(98524-19-7)Related Product Information

• 9(R,S)-Hydroperoxy-10(E),12(Z)-octadecadienoic?Acid?
• (+/-)9-HODE CHOLESTERYL ESTER
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• 13(S)-HODE
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• HODE,(+/-)13-HODE
• 13(S)-HODE-D4
• 13(R)-HODE CHOLESTERYL ESTER
• 13(S)-HODE CHOLESTERYL ESTER
• (+/-)13-HODE CHOLESTERYL ESTER