2097130-84-0

Upstream product

• 3384-24-5 9-hydroxystearic acid 
• 112-67-4 n-hexadecanoyl chloride 
• 3937-56-2 1,9-Nonanediol 
• 98847-00-8 9-<(2H-tetrahydropyran-2-yl)oxy>nonan-1-ol 
• 70863-80-8 9-((tetrahydro-2H-pyran-2-yl)oxy)nonan-1-al 
• 89359-54-6 9-bromo-1-nonene 
• 112-31-2 caprinaldehyde 
• 862844-62-0 nonadec-1-en-10-ol 
• 2447-53-2 9-hydroxy-octadecanoic acid methyl ester 
• 112-62-9 Methyl oleate 
• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 18719-24-9 oct-7-enoic acid 
• 57-10-3 1-hexadecylcarboxylic acid 
• 4114-74-3 9-oxo-octadecanoic acid 

Relevant academic research and scientific papers

Stereochemistry of Endogenous Palmitic Acid Ester of 9-Hydroxystearic Acid and Relevance of Absolute Configuration to Regulation

Lipids have fundamental roles in the structure, energetics, and signaling of cells and organisms. The recent discovery of fatty acid esters of hydroxy fatty acids (FAHFAs), lipids with potent antidiabetic and anti-inflammatory activities, indicates that our understanding of the composition of lipidome and the function of lipids is incomplete. The ability to synthesize and test FAHFAs was critical in elucidating the roles of these lipids, but these studies were performed with racemic mixtures, and the role of stereochemistry remains unexplored. Here, we synthesized the R- and S- palmitic acid ester of 9-hydroxystearic acid (R-9-PAHSA, S-9-PAHSA). Access to highly enantioenriched PAHSAs enabled the development of a liquid chromatography-mass spectrometry (LC-MS) method to separate and quantify R- and S-9-PAHSA, and this approach identified R-9-PAHSA as the predominant stereoisomer that accumulates in adipose tissues from transgenic mice where FAHFAs were first discovered. Furthermore, biochemical analysis of 9-PAHSA biosynthesis and degradation indicate that the enzymes and pathways for PAHSA production are stereospecific, with cell lines favoring the production of R-9-PAHSA and carboxyl ester lipase (CEL), a PAHSA degradative enzyme, selectively hydrolyzing S-9-PAHSA. These studies highlight the role of stereochemistry in the production and degradation of PAHSAs and define the endogenous stereochemistry of 9-PAHSA in adipose tissue. This information will be useful in the identification and characterization of the pathway responsible for PAHSA biosynthesis, and access to enantiopure PAHSAs will elucidate the role of stereochemistry in PAHSA activity and metabolism in vivo.

A General Approach to Intermolecular Olefin Hydroacylation through Light-Induced HAT Initiation: An Efficient Synthesis of Long-Chain Aliphatic Ketones and Functionalized Fatty Acids

Herein, an operationally simple, environmentally benign and effective method for intermolecular radical hydroacylation of unactivated substrates by employing photo-induced hydrogen atom transfer (HAT) initiation is described. The use of commercially available and inexpensive photoinitiators (Ph2CO and NHPI) makes the process attractive. The olefin hydroacylation protocol applies to a wide array of substrates bearing numerous functional groups and many complex structural units. The reaction proves to be scalable (up to 5 g). Different functionalized fatty acids, petrochemicals and naturally occurring alkanes can be synthesized with this protocol. A radical chain mechanism is implicated in the process.

Synthesis of chemically edited derivatives of the endogenous regulator of inflammation 9-PAHSA

Fatty acid esters of hydroxy fatty acids (FAHFAs) are a growing class of natural products found in organisms ranging from plants to humans. The roles these endogenous derivatives of fatty acids play in biology and their novel pathways for controlling inflammation have increased our understanding of basic human physiology. FAHFAs incorporate diverse fatty acids into their structures, however, given their recent discovery non-natural derivatives have not been a focus and as a result structure-activity relationships remain unknown. The importance of the long chain hydrocarbons extending from the ester linkage as they relate to anti-inflammatory activity is unknown. Herein the systematic removal of carbons from either the hydroxy fatty acid or fatty acid regions of the most studied FAHFA, palmitic acid ester of 9-hydroxystearic acid (9-PAHSA), was achieved and these synthetic, abridged analogs were tested for their ability to attenuate IL-6 production. Reduction of the carbon chain lengths of the 9-hydroxystearic acid portion or palmitic acid hydrocarbon chain resulted in lower molecular weight analogs that maintained anti-inflammatory activity or in one case enhanced activity.

Asymmetric Synthesis of Saturated Hydroxy Fatty Acids and Fatty Acid Esters of Hydroxy Fatty Acids

The recent discovery of a novel class of endogenous lipids, named Fatty Acid esters of Hydroxy Fatty Acids (FAHFAs), that present antidiabetic and anti-inflammatory activities, has attracted the interest on hydroxy fatty acids (HFAs) and their derivatives

Organic matter enantiomer pure OA and uses of organic matter enantiomer pure OA in preparation of drugs for type 2 diabetes and vascular complications

The invention belongs to the technical field of medicinal chemistry and medicine, and relates to a novel organic matter enantiomer pure octadecanoic acid (OA) extracted from natural food, a preparation method and uses thereof. According to the present invention, the test results show that OA has good pharmacological activity and pharmacokinetic properties in the fields of blood glucose lowering, blood fat regulating, inflammation resistance, insulin sensitivity enhancement and the like, and can further be used as the active ingredient to preparing pharmacological compounds for treatment of various diabetic complications including but being not limited to atherosclerosis, cardiovascular and cerebrovascular diseases, lower extremity atherosclerosis, diabetic foot, diabetic peripheral neuropathy, diabetic nephropathy, diabetic cognitive dysfunction, diabetic retinopathy and the like; the preparation method has characteristics of relatively simple operation, easy industrial production andthe like; and the organic matter enantiomer pure OA of the present invention has significantly enhanced blood glucose lowering activity, significantly enhanced blood fat regulating activity and significantly enhanced anti-inflammatory activity compared to the un-modified OA, and further ha excellent pharmacokinetics. The structure of the organic matter enantiomer pure OA is defined in the specification.

Lipids That Increase Insulin Sensitivity And Methods Of Using The Same

The invention provides, inter alia, fatty acyl hydroxy fatty acid (FAHFA; a novel class of estolide-related molecules) and diagnostic and treatment methods for a variety of disorders—including diabetes-related disorders, Metabolic Syndrome, polycystic ovarian syndrome, cancer, and inflammatory disorders—using them; as well as methods of screening for additional compounds that are useful in treating these disorders and/or that modulate FAHFA levels, FAHFA-mediated signaling, and FAHFA-mediated biological effects.

LIPIDS THAT INCREASE INSULIN SENSITIVITY AND METHODS OF USING THE SAME

The invention provides, inter alia, fatty acyl hydroxy fatty acid (FAHFA; a novel class of estolide-related molecules) and diagnostic and treatment methods for a variety of disorders- including diabetes-related disorders, Metabolic Syndrome, polycyctic ov