palmitoleic acid

Palmitoleic acid ((Z)-Hexadec-9-enoic acid) 是脂肪酸的组成部分，能够预防 SHRSP 大鼠因脑血管疾病引起的死亡。

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.

trans-Palmitelaidic Acid (trans-Palmitoleic acid) 是palmitoleic acid 的反式异构体。Palmitoleic acid 是血清和组织中最丰富的脂肪酸之一。

Pam2Cys是一种L-半胱氨酸硫醚，在该化合物中，硫醇基团的氢被2,3-二(palmitoyloxy)丙基取代。它作为Toll样受体2激动剂和Mycoplasma genitalium代谢产物发挥作用。此外，Pam2Cys与十六碳烯酸功能相关。

1,2-Dipalmitoleoyl-3-11(Z)-octadecenoyl-rac-glycerol 是一种三酰甘油，包含了cis-Vaccenic acid与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 是棕榈油酸的衍生物，可用作合成多种化合物的中间体。

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 是米托蒽醌 (MTO) 与棕榈酸结合的棕榈基脂质，其抗癌活性得以显著提升。当摩尔比1:1时，将mono-Pal-MTO与di-Pal-MTO的纳米颗粒组合使用，可有效递送siRNA至细胞内，进一步增强其抗癌效果。

di-Pal-MTO，一种棕榈油基脂质，由抗癌活性分子米托蒽醌(MTO)与棕榈油酸以1:1的摩尔比结合形成。当以纳米颗粒形式将mono-Pal-MTO与di-Pal-MTO联合使用时，能有效递送siRNA至细胞内，并显著增强抗癌活性。

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.

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are recent discoveries in endogenous lipids that are influenced by dietary changes such as fasting and high-fat diets, showing a link with enhanced insulin sensitivity in mice. These compounds typically feature a C-16 or C-18 fatty acid (e.g., palmitoleic, palmitic, oleic, or stearic acid) bound to a hydroxy group on another C-16 or C-18 fatty chain. A specific FAHFA, 9-POHSA, consists of palmitoleic acid connected at the hydroxy stearic acid’s 9th position. This molecule, in particular, exhibits notably increased levels in the serum of glucose-tolerant AG4OX mice, which express the Glut4 glucose transporter predominantly in their adipose tissue. Given the broader family of FAHFAs' roles in enhancing glucose tolerance, promoting insulin secretion, and exerting anti-inflammatory effects, 9-POHSA emerges as a potential bioactive lipid involved in managing metabolic syndrome and inflammation.

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.

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are recently discovered lipids that play a role in the body's response to fasting and high-fat diets, with a link to insulin sensitivity. These compounds consist of a long-chain fatty acid (such as palmitoleic, palmitic, oleic, or stearic acid) bonded to a hydroxy fatty acid, both ranging in length from C-16 to C-18. Specifically, 12-OAHSA is a type of FAHFA where oleic acid is attached to the 12th carbon of hydroxy stearic acid. Within the FAHFA family, OAHSAs are particularly notable for their high concentration in the serum of AG4OX mice, a strain engineered to express the Glut4 glucose transporter predominantly in their adipose tissue, which demonstrates an enhanced glucose tolerance.

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are lipids that are modulated by dietary changes such as fasting and high-fat diets, and they play a role in insulin sensitivity. These compounds generally consist of a fatty acid chain of either 16 or 18 carbons (for example, palmitoleic, palmitic, oleic, or stearic acid) esterified to a similarly long hydroxy fatty acid. One specific FAHFA, 9-SAHSA, features stearic acid esterified at the 9th carbon of hydroxy stearic acid. The concentration of 9-SAHSA is notably increased in the serum of glucose-tolerant AG4OX mice, which specifically express the Glut4 glucose-transporting protein in adipose tissue.