9-OAHSA

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are newly identified endogenous lipids regulated by fasting and high-fat feeding and associated with insulin sensitivity. Structurally, these esters are comprised of a C-16 or C-18 fatty acid (e.g., palmitoleic, palmitic, oleic, or stearic acid) linked to a hydroxylated C-16 or C-18 lipid. 9-OAHSA is a form of FAHFA in which oleic acid is esterified to 9-hydroxy stearic acid. Among the FAHFA family members, OAHSAs are the most abundantly expressed in the serum of glucose tolerant AG4OX mice, which overexpress the Glut4 glucose transporter specifically in adipose tissue.

9-OAHSA is a fatty acid ester of hydroxy fatty acids (FAHFAs). 9-OAHSA shows anti-inflammatory effects via inhibiting cytokine production and reduces IL-1β and IL-6 expression. 9-OAHSA is also a protective molecule to prevent colon carcinoma cells from apoptotic cell death[1][2][3].

ChEBI: 9-[(9Z)-octadecenoyloxy]octadecanoic acid is a fatty acid ester obtained by formal condensation of the carboxy group of oleic acid with the hydroxy group of 9-hydroxyoctadecanoic acid. It is a fatty acid ester and a monocarboxylic acid. It is functionally related to an oleic acid and a 9-hydroxyoctadecanoic acid. It is a conjugate acid of a 9-[(9Z)-octadecenoyloxy]octadecanoate.

[1] Zhu QF, et al. Highly sensitive determination of fatty acid esters of hydroxyl fatty acids by liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Sep 1;1061-1062:34-40.2. DOI:10.1016/j.jchromb.2017.06.045
[2] Ding J, et al. In-Silico-Generated Library for Sensitive Detection of 2-Dimethylaminoethylamine Derivatized FAHFA Lipids Using High-Resolution Tandem Mass Spectrometry. Anal Chem. 2020 Apr 21;92(8):5960-5968. DOI:10.1021/acs.analchem.0c00172
[3] Li L, et al. Fatty acid esters of hydroxy fatty acids: A potential treatment for obesity-related diseases. Obes Rev. 2024 Mar 10:e13735. DOI:10.1111/obr.13735