palmitoleic acid

Palmitoleic acid ((Z)-Hexadec-9-enoic acid) is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.

Palmitoleic acid alkyne, an ω-terminal alkyne derivative of palmitoleic acid, facilitates click chemistry applications. This compound has played a crucial role in examining protein palmitoylation processes. Specifically, the cis form of palmitoleic acid alkyne selectively tags wild-type Wnt3a protein within mouse fibroblast L-cells expressing Wnt3a and its secretion in conditioned media, distinguishing itself from the trans form and proving ineffective against the S209A mutant Wnt3a.

Palmitoleic acid, an ω-7 monounsaturated fatty acid found in macadamia and sea buckthorn oils, enhances both basal and insulin-stimulated glucose uptake, as well as Glut4 protein levels in 3T3-L1 adipocytes at a 200 µM concentration. Ex vivo, at a dosage of 300 mg/kg per day, it significantly increases glucose uptake and both aerobic and anaerobic glycolysis, while decreasing de novo fatty acid synthesis and the activity of lipogenic enzymes, specifically ATP citrate lyase (ACL) and glucose-6-phosphate dehydrogenase (G6PDH), in isolated murine adipocytes. Furthermore, the dietary administration of palmitoleic acid at 300 mg/kg mitigates high-fat diet-induced insulin resistance and liver inflammation in mice.

Palmitoleic acid-13C16 is a 13C-labeled variant of Palmitoleic acid. As a constituent of fatty acids, Palmitoleic acid helps prevent death caused by cerebrovascular diseases in SHRSP rats.

Palmitoleic acid-d14 is a deuterated form of Palmitoleic acid. As a component of fatty acids, Palmitoleic acid can prevent death caused by cerebrovascular diseases in SHRSP rats.

Palmitoleic acid-d13 is the deuterated form of Palmitoleic acid. Palmitoleic acid, a component of fatty acids, has the potential to prevent death from cerebrovascular diseases in SHRSP rats.

Palmitelaidic Acid (trans-Palmitoleic acid) is one of the most abundant fatty acids in serum and tissue.

Methyl palmitoleate (Standard) is the standard substance of Methyl palmitoleate, and it is applicable for quantitative analysis, quality control, and related research in biochemical experiments. O-PHOSPHO-L-SERINE is an ester of serine and phosphate, which are normal metabolites in human biofluids.O-phospho-L-serine is a phagocytosis inhibitor that inhibits glial cell proliferation and cone cell regeneration after photodamage.

Pam2Cys is an L-cysteine thioether where the hydrogen of the thiol group is replaced by a 2,3-di(palmitoyloxy)propyl group. It acts as a Toll-like receptor 2 agonist and a metabolite of Mycoplasma genitalium. Additionally, Pam2Cys is associated with the function of palmitoleic acid.

1,2-Dipalmitoleoyl-3-11(Z)-octadecenoyl-rac-glycerol is a triacylglycerol that comprises cis-Vaccenic acid and Palmitoleic acid.

Tripalmitolein is a triacylglycerol that contains palmitoleic acid at the sn-1, sn-2, and sn-3 positions. It reduces red blood cell deformability in a concentration-dependent manner in a Reid's filtration assay. Hepatic levels of 1,2,3-tripalmitoleoyl-rac-glycerol are increased in the JAK2L mouse model of hepatic steatosis. Tripalmitolein plasma levels are decreased in renal patients before dialysis.

Palmitoleoyl Chloride is a derivative of palmitoleic acid and can be used as an intermediate in the synthesis of a variety of compounds.

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 either a C-16 or C-18 hydroxy substituent. 12-PAHSA is a FAHFA in which palmitic acid is esterified at the 12th carbon of hydroxy stearic acid. Among the FAHFA family members, PAHSAs are the most abundant in the adipose tissue of glucose tolerant AG4OX mice, which overexpress the Glut4 glucose transporter specifically in adipose tissue. 12-PAHSA is present at 2- to 3-fold higher levels in adipose tissue of AG4OX mice compared to wild type mice. Levels of 12-PAHSA are also higher in fasted wild-type mice compared to fed mice and are reduced upon high-fat diet-induced obesity in insulin-resistant mice.

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.

Palmitoleic acid is a common constituent of the triglycerides of human adipose tissue. Palmitoleic acid-based diets raise low-density lipoprotein cholesterol and diminish high-density lipoprotein cholesterol, even when dietary intake of cholesterol is maintained at a low level. Palmitelaidic acid is the trans isomer of the 16:1 fatty acid palmitoleic acid. While its effects on cholesterol levels are poorly studied, palmitelaidic acid can have very different effects from those of palmitoleic acid on lipid metabolism and mobilization. Palmitelaidic acid methyl ester is an ester version of the free acid which may be more amenable for the formulation of fatty acid-containing diets and dietary supplements.

1,3-Dipalmitoleoyl-rac-glycerol is a diacylglycerol with palmitoleic acid at the sn-1 and sn-3 positions. It selectively inhibits α-glucosidase from S. cerevisiae over rat enzyme (IC50s = 4.45 and 9,326.5 μM, respectively). 1,3-Dipalmitoleoyl-rac-glycerol has been used in the formation of lipid bilayers to study the effects of membrane composition and the ionophore valinomycin on membrane potential.

Mono-Pal-MTO, a palm oil-derived lipid formed by integrating the anticancer agent mitoxantrone (MTO) with palmitoleic acid, exhibits enhanced anticancer activity and efficient siRNA cell delivery when its nanoparticles are mixed with those of di-Pal-MTO at a molar ratio of 1:1 [1].

Di-Pal-MTO, a lipid derivative synthesized from palm oil by integrating the anticancer agent mitoxantrone (MTO) with palmitoleic acid, exhibits enhanced anticancer activity and efficient siRNA cell delivery when nanoparticles of mono-Pal-MTO and di-Pal-MTO are combined at a molar ratio of 1:1 [1].

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are lipids influenced by dietary changes, playing a crucial role in insulin sensitivity. These compounds typically consist of a C-16 or C-18 fatty acid (for example, palmitoleic, palmitic, oleic, or stearic acid) linked to a hydroxy fatty acid with the same carbon chain length. 13-PAHSA, a derivative where palmitic acid is esterified to 13-hydroxy stearic acid, is notably prevalent in the adipose tissue of glucose-tolerant AG4OX mice, which exhibit enhanced glucose transport via the overexpression of the Glut4 glucose transporter. This observation, along with the metabolic benefits seen from other FAHFAs—including improved glucose tolerance, stimulated insulin secretion, and anti-inflammatory properties—suggests that 13-PAHSA may function as a bioactive lipid beneficial in managing metabolic syndrome and inflammation.

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are a class of endogenous lipids whose levels are modulated by fasting and high-fat diets, and they play a role in insulin sensitivity. These compounds consist of a fatty acid—either a C-16 or C-18, such as palmitoleic, palmitic, oleic, or stearic acid—esterified to a hydroxylated C-16 or C-18 lipid. One notable FAHFA, 9-PAHSA, features an ester linkage between palmitic acid and 9-hydroxy stearic acid. PAHSAs, with 9-PAHSA being the most prevalent isomer, are significantly found in the serum and both white and brown adipose tissues of glucose-tolerant AG4OX mice, which express the Glut4 gene in adipose tissue, enhancing insulin sensitivity. Additionally, 9-PAHSA is abundant in wild type and AG4OX mice and present in humans, though at reduced levels in those with insulin resistance. 9-PAHSA is associated with improved glucose tolerance, enhanced insulin secretion, and anti-inflammatory effects in mice. The compound 19-PAHSA^13C4 represents an isotopically enriched form of this polyunsaturated fatty acid.

13-POHSA (palmitoleic acid esterified to 13-hydroxy stearic acid) is a type of branched fatty acid esters of hydroxy fatty acids (FAHFAs), which have recently been discovered as endogenous lipids whose levels are modulated by fasting and high-fat diets, and are linked to insulin sensitivity in mice. Notably, the concentration of 13-POHSA in the serum significantly increases in glucose tolerant AG4OX mice, a model that overexpresses the Glut4 glucose transporter in adipose tissue, suggesting its physiological relevance. Like other FAHFAs, 13-POHSA is believed to enhance glucose tolerance, promote insulin secretion, and exert anti-inflammatory properties, highlighting its potential importance in managing metabolic syndrome and inflammation.

Branched fatty acid esters of hydroxy fatty acids (FAHFAs), endogenous lipids influenced by fasting and high-fat diets, are linked to improved insulin sensitivity in mice. These molecules consist of a C-16 or C-18 fatty acid (e.g., palmitoleic, palmitic, oleic, or stearic acid) bonded to a C-16 or C-18 hydroxy fatty acid. A specific FAHFA, 5-POHSA, features palmitoleic acid esterified with hydroxy stearic acid at the 5th carbon. Elevated levels of 5-POHSA in the serum of AG4OX mice, which express high levels of the Glut4 glucose transporter in adipose tissue, correlate with glucose tolerance. Like other FAHFAs that enhance glucose tolerance, stimulate insulin secretion, and exhibit anti-inflammatory properties, 5-POHSA may play a role in managing metabolic syndrome and inflammation.

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are endogenous lipids that are influenced by fasting and high-fat diets and linked to improved insulin sensitivity in mice. These compounds typically feature a chain of either 16 or 18 carbon atoms (for example, palmitoleic, palmitic, oleic, or stearic acid) esterified with a hydroxy fatty acid chain of similar length. One specific FAHFA, known as 5-OAHSA, consists of oleic acid bonded to the fifth carbon of hydroxy stearic acid. Within the FAHFA family, OAHSAs exhibit the highest serum levels in AG4OX mice, which are known for their glucose tolerance attributed to the overexpression of the Glut4 glucose transporter in adipose tissue.

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are a class of endogenous lipids whose levels are modulated by fasting and high-fat diets and are linked to insulin sensitivity. These compounds typically consist of a C-16 or C-18 fatty acid, such as palmitoleic, palmitic, oleic, or stearic acid, esterified to a hydroxylated C-16 or C-18 lipid. One specific form of FAHFA, known as 9-OAHSA, involves the esterification of oleic acid to 9-hydroxy stearic acid. Within the FAHFA family, OAHSAs notably represent the predominant form found in the serum of glucose-tolerant AG4OX mice, which uniquely overexpress the Glut4 glucose transporter in adipose tissue.