| Identification | Back Directory | [Name]
5-PAHSA | [CAS]
1481636-41-2 | [Synonyms]
5-PAHSA
QBGKCWKQYJQHJX-UHFFFAOYSA-N
Octadecanoic acid, 5-[(1-oxohexadecyl)oxy]- | [Molecular Formula]
C34H66O4 | [MOL File]
1481636-41-2.mol | [Molecular Weight]
538.89 |
| Chemical Properties | Back Directory | [storage temp. ]
-20°C | [solubility ]
DMF: 20 mg/ml; DMSO: 15 mg/ml; Ethanol: 20 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml | [form ]
Solid |
| Hazard Information | Back Directory | [Uses]
5-PAHSA is used in biological studies for the discovery of a class of endogeneous mammalian lipids with anti-diabetic and anti-inflammatory effects. | [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. 5-PAHSA is a FAHFA in which palmitic acid is esterified at the 5th carbon of hydroxy stearic acid. PAHSA isoforms are the most abundant forms of FAHFA identified in the adipose tissue of glucose tolerant AG4OX mice. PAHSAs are synthesized in vivo in both mice and humans and are regulated by fasting and high-fat feeding in mice. PAHSA levels correlate highly with insulin sensitivity and are reduced in adipose tissue and serum of insulin-resistant humans. PAHSA administration lowers ambient glycemia, improves glucose tolerance, and stimulates GLP-1 and insulin secretion in mice.[Cayman Chemical] | [Definition]
ChEBI:5-PAHSA is a FAHFA obtained by formal condensation of the carboxy group of palmitic acid with the hydroxy group of 5-hydroxystearic acid. It has a role as a human metabolite, an anti-inflammatory agent and a hypoglycemic 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 5-PAHSA(1-). | [General Description]
Palmitic acid and hydroxystearic acid (PAHSA) containing (O-acyl)-hydroxy fatty acids are being found in tissues and serum extracts of mouse and human. | [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. |
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