CAS 2042646-31-9

12-[[(9Z)-1-Oxo-9-hexadecen-1-yl]oxy]octadecanoic acid

Description:

The chemical substance known as 12-[[(9Z)-1-oxo-9-hexadecen-1-yl]oxy]octadecanoic acid, with the CAS number 2042646-31-9, is a fatty acid derivative characterized by its long hydrocarbon chain and functional groups. This compound features a carboxylic acid group, which is typical of fatty acids, and an ester linkage due to the presence of an alkoxy group derived from a hexadecenyl moiety. The presence of a double bond in the hexadecenyl chain indicates that it is an unsaturated fatty acid, which can influence its physical properties, such as melting point and solubility. The specific configuration of the double bond (9Z) suggests a cis arrangement, which is common in naturally occurring unsaturated fatty acids. This compound may exhibit biological activity and could be relevant in various fields, including biochemistry and materials science, particularly in the study of lipid metabolism or the development of surfactants and emulsifiers. Its unique structure may also contribute to its potential applications in pharmaceuticals or nutraceuticals.

Formula: C₃₄H₆₄O₄

InChI: InChI=1/C34H64O4/c1-3-5-7-9-10-11-12-13-14-15-20-23-27-31-34(37)38-32(28-24-8-6-4-2)29-25-21-18-16-17-19-22-26-30-33(35)36/h11-12,32H,3-10,13-31H2,1-2H3,(H,35,36)/b12-11-

InChI key: InChIKey=XSYATLPMKFNWBI-QXMHVHEDNA-N

SMILES: C(OC(CCCCCCC/C=C\CCCCCC)=O)(CCCCCCCCCCC(O)=O)CCCCCC

Synonyms:

• 12-[[(9Z)-1-Oxo-9-hexadecen-1-yl]oxy]octadecanoic acid
• 12-POHSA
• Octadecanoic acid, 12-[[(9Z)-1-oxo-9-hexadecen-1-yl]oxy]-

12-POHSA

CAS: 2042646-31-9

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) have emerged as significant regulators of metabolic processes, influenced by dietary changes such as fasting and high-fat diets, and are linked to improved insulin sensitivity in mice. These compounds typically feature a fatty acid chain, either C-16 or C-18 in length (for example, palmitoleic, palmitic, oleic, or stearic acid), esterified to a hydroxy fatty acid of similar length. A specific FAHFA, 12-POHSA, involves the esterification of palmitoleic acid to the 12th carbon of stearic acid. Notably, 12-POHSA levels are markedly higher in the serum of AG4OX mice, which exhibit enhanced glucose tolerance due to overexpression of the Glut4 glucose transporter in adipose tissue. Given the capacity of FAHFAs to enhance glucose tolerance, stimulate insulin secretion, and exert anti-inflammatory actions, 12-POHSA holds potential as a bioactive lipid implicated in managing metabolic syndrome and inflammation.

Formula: C₃₄H₆₄O₄

Color and Shape: Solid

Molecular weight: 536.9

Ref: TM-T84429