9-PAHSA

Description

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-PAHSA is a FAHFA in which palmitic acid is esterified to 9-hydroxy stearic acid. PAHSAs are the most abundant forms of FAHFA in serum as well as white and brown adipose tissues of glucose tolerant AG4OX mice, which overexpress Glut4 specifically in adipose tissue. 9-PAHSA is the predominant isomer of PAHSA in wild type and AG4OX mice. It is found in humans and is reduced in the serum and adipose tissues of insulin-resistant humans. 9-PAHSA improves glucose tolerance, stimulates insulin secretion, and has anti-inflammatory effects in mice.

Uses

9-(Palmitoyloxy)octadecanoic acid or 9-PAHSA might be used as a standard to confirm the quantification of fatty acid esters of hydroxy fatty acids (FAHFAs) by liquid chromatography–mass spectrometry (LC-MS). It has also been used to study its effect on apoptosis.

Uses

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-PAHSA is a FAHFA in which palmitic acid is esterified to 9-hydroxy stearic acid. PAHSAs are the most abundant forms of FAHFA in serum as well as white and brown adipose tissues of glucose tolerant AG4OX mice, which overexpress Glut4 specifically in adipose tissue. 9-PAHSA is the predominant isomer of PAHSA in wild type and AG4OX mice. It is found in humans and is reduced in the serum and adipose tissues of insulin-resistant humans. 9-PAHSA improves glucose tolerance, stimulates insulin secretion, and has anti-inflammatory effects in mice.[Cayman Chemical]

Definition

ChEBI: 9-PAHSA is a FAHFA (fatty acid ester of a hydroxy fatty acid) obtained by formal condensation of the carboxy group of palmitic acid with the hydroxy group of 9-hydroxyoctadecanoic acid (9-hydroxystearic acid). It has a role as a human metabolite, a hypoglycemic agent and an anti-inflammatory agent. It is a FAHFA and a long-chain fatty acid. It is functionally related to a hexadecanoic acid and an octadecanoic acid. It is a conjugate acid of a 9-PAHSA(1-).

General Description

9-(Palmitoyloxy)octadecanoic acid (9-PAHSA) is a palmitic acid ester of 9-hydroxystearic acid.

Biochem/physiol Actions

Palmitic acid and hydroxystearic acid (PAHSA) levels correlate highly with insulin sensitivity and are reduced in adipose tissue and serum of insulin-resistant humans. In adipocytes, PAHSAs signal through G-protein-coupled receptor 120 (GPR120) to enhance insulin-stimulated glucose uptake. PAHSAs are fatty acid esters of hydroxy fatty acids (FAHFAs), which are endogenous lipids with the potential to treat diabetes and inflammation.

Raw materials

Preparation Products