Lipides

<p>Applications (3β,5β)-3-Hydroxycholan-24-oic acid has been used for the study of the activation of β1 subunit-​containing BK channels with respect to the structure of monohydroxylated bile acids.<br>References Bukiya, A.N., ey al.: J. Lipid. Res., 49, 2441-2451 (2008)<br></p>

<p>Applications 8-Dehydrocholesterol is an intermediate in the synthesis of Zymostenol, which is the derivative of Zymosterol (Z701520), an sterol intermediate in the biosynthesis of cholesterol (C432501).<br>References Roland, E.D., et al.: J. Am. Chem. Soc., 111, 278 (1989); Echevarria, F., et al.: J. Biol. Chem., 265, 8484 (1990); Baranovskii, A.V., et al.: Russian. J. Bioorg. Chem., 28, 250 (2002); Schoenheimer, et al.: J. Biol. Chem., 105, 355 (1934);<br></p>

<p>Applications Sodium oleate (cas# 143-19-1) is a useful research chemical.<br></p>

<p>Applications Production of ceramide occurs upon hydrolysis of sphingomyelin by a specific isoform of phospholipase C, appropriately named sphingomyelinase.<br>References Gu, Q, et al.: Anal. Biochem., 244, 347 (1997), Perry, D.K., et al.: Trends Cardiovasc. Med., 6, 158 (1996), Clayton, R.B., et al.: J. Lipid Res., 15, 557 (1974),<br></p>

<p>Applications Cholesterol analog. Useful for treatment of hyperlipemia, arteriosclerosis, diabetes, obesity.<br>References Watson, K., et al.: J. Clin. Invest., 93, 2106 (1994), Wada, T., et al.: Circ. Res., 84, 166 (1999), Engelse, M., et al.: Cardiovasc. Res., 52, 281 (2001), Landis, M., et al.: J. Biol. Chem., 277, 4713 (2002),<br></p>

<p>Applications (11Z)-11-Eicosenoic Acid, is a monostaturated fatty acid. The combined C20:1 isomers constitute 70% of the total fatty acid pool in jojoba seed oil isolated from plants in the Arizona desert.<br>References Miwa, T.K. et al.: J. Am. Chem. Soc. 48(6), 259-264 (1971).;<br></p>

<p>Applications 12-Hydroxystearic Acid is used in edible vegetable oils and organogels.<br>References Rogers, M. et al.: Soft. Matt., 4, 1483 (2008); Hughes, N. et al.: Trends. Food. Sci. Tech., 20, 470 (2009);<br></p>

<p>Stability Temperature Sensitive<br>Applications A biologically active, cell permeable, but nonphysiologic ceramide analog. It induces phosphorylation on Thr-669 in A-431 cells by stimulation of ceramide-activated protein kinase. It stimulates IL-2 secretion and induces apoptosis.<br>References Mathias, S., et al.: Proc. Natl. Sci. USA, 88, 10009 (1991), Mathias, S., et al.: Science, 259, 519 (1993), Jarvis, W.D., et al.: Proc. Natl. Acad. Sci. USA, 91, 73 (1994)<br></p>

<p>Applications (8Z,11Z,14Z)-8,11,14-Heptadecatrienoic Acid, is a naturally occurring hydroxylated fatty acid that is found in Acinetobacter species. It acts as a partial agonist of free fatty acid receptor 1 (FFAR1/GPR40) and GPR84 receptors in vitro. It also inhibits bovine hepatic ligase (Ki = 4.4 μM) and mouse kidney mitochondrial medium-chain acyl-CoA synthetase by 48% at a concentration of 40 μM.<br>References Moss, C.W., et al.: J. Clin. Microbiol. 26(3), 484-492 (1988).; Kaspersen, M.H., et al.: Med. Chem. Commun. 8(6), 1360-1365 (2017).<br></p>

<p>Applications A biologically active, cell permeable, but nonphysiologic ceramide analog. It stimulates protein phosphatase 2A at concentrations as low as 10 nM and activiates MAP kinase. It induces apoptosis and inhibits glycoproptein traffic by the secretory pathway.<br>References Liu, Z., et al.: J. Neurochem., 106, 2463 (2008), Heakal, Y., et al.: Mol. Cancer Res., 7, 724 (2009), Chen-Quay, S., et al.: J. Pharm. Sci., 98, 606 (2009), Mahdy, A., et al.: Mol. Ther., 17, 430 (2009),<br></p>

<p>Applications Labelled Sitosterol (S497050). A common sterol in plants. Isolated from wheat germ oil, corn oil. Antilipemic. Used in the treatment of prostatic adenoma.<br>References Tanaka, et al.: J. Biochem., 17, 483 (1933), Nigro, N.D., et al.: J. Natl. Cancer Inst., 69, 103 (1982),<br></p>

<p>Applications (E)-2-Octenoyl-L-carnitine Inner Salt is an L-carnitine metobolite which are often used to diagnose specific inherited metabolic diseases especially glucose related ones.<br>References Yang, S. et l.: J. Chrom. B., Anal. Tech. Biomed. Life Sci., 857, 251 (2007); Anderson, K. et al.: Mol. Endocrinol., 26, 281 (2012);<br></p>

<p>Applications Allolithocholic acid is used as steroid compound as T regulatory lymphocyte modulators and uses for treatment of inflammatory or autoimmune disorders.<br>References Littman, D. R., et al.: PCT Int. Appl. 160pp. (2020)<br></p>

<p>Applications (R,S,R)-2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)-imidazole (THI) inhibits sphinogosine-1-phosphate (S1P) lyase for treatment of autoimmune disorders.<br>References Zhang, H., et al.: Tetrahedron, 69, 4041 (2013); Bagdanoff, J.T., et al.: J. Med. Chem., 53, 8650 (2010); Bagdanoff, J.T., et al.: J. Med. Chem., 52, 3941 (2009)<br></p>

<p>Applications Glycocholic Acid (cas# 475-31-0) is a useful research chemical.<br></p>

<p>Stability Hygroscopic, moisture sensitive<br>Applications Stearoyl L-α-Lysolecithin is an bioactive lysophosphatidylcholine derived compound found to be released by bronchial epithelial cells. Stearoyl L-α-Lysolecithin have also been utilized in the development of liposomes and michelles by drug transdermal delivery devices.<br>References Zhuge, Y., et al.: Allergy Asthma Immunol Res., 6, 66 (2014)<br></p>

<p>Applications A labelled cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones.<br>References Brindle, J., et al.: Nat. Med., 12, 1439 (2002), Lindon, J., et al.: Biomarkers, 9, 1 (2004), Holmes, E., et al.: Cell, 134, 714 (2008),<br></p>

<p>Stability Moisture, Temperature Sensitive; Hygroscopic<br>Applications A putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammatory processes. It mobilizes intracellular calcium stores, decreases cellular cAMP, activates phospholipase D and does not inhibitprotein kinase C.<br>References Yeh, C., et al.: Am. J. Physiol., 296, H1193 (2009), Hagen, N., et al.: J. Biol. Chem., 284, 11346 (2009), Kuehnel, M., et al.: J. Cell Sci., 122, 499 (2009),<br></p>

<p>Applications Cholic Acid-d4 is a labelled analog of Cholic acid (C432600) which is a choleretic produced by, and isolated from liver cells.<br>References Nomoto, M., et al.: Biol. Pharm. Bull., 32, 172 (2009), Simonsen, H., et al.: J. Agric. Food Chem., 57, 2056 (2009), Miyata, M., et al.: Drug Metab. Disposition, 37, 338 (2009),<br></p>

<p>Applications Phytantriol 74563-64-7 (cas# 74563-64-7) is a useful research chemical.<br></p>

<p>Stability Light Sensitive<br>Applications (5Z)​-5-​Dodecenoic acid is a fatty acid and a component of the essential oils of certain plants, such as Paeonia lactiflora Pall., and is used as biofuel.<br>References Liu, P.; et al.: Industrial Crops and Products, 107, 260 (2017); Xu, L.; et al.: Renewable Energy, 130, 910 (2019).<br></p>

<p>Applications A Cortisone derivative, a glucocorticoid.<br>References Mickelson, K., et al.: Biochemistry, 20, 6211 (1981), Westphal, U., et al.: J. Steroid Biochem., 19, 1 (1983),<br></p>

<p>Applications (-)-Maackiain (CAS# 2035-15-6) is a useful research chemical compound.<br></p>

<p>Applications A metabolite of Cholesterol. Cholesterol oxidation product having cytotoxicity effects.<br>References Higley, N., et al.: Food Chem. Toxicol., 22, 983 (1984), Emanuel, H., et al.: J. Food Sci., 56, 843 (1991), Kilsdonk, E., et al.: J. Lipid Res., 36, 505 (1995), Cantwell, H., et al.: Cell Biol. Toxicol., 14, 401 (1998),<br></p>

<p>Applications Isodeoxycholic Acid is used for comprehensive bile acid profiling in hereditary intrahepatic cholestasis.<br>References Liu, T., et al.: Liver Int. 38, 1676 (2018)<br></p>

<p>Applications A triterpenoid known for its anti-inflammatory properties, is commonly present in several medicinal plants. Inhibits secretory phospholipase A2.<br>References Andrikopoulos, N., et al.: J. Med. Food, 5, 1 (2002), Lanteri, S., et al.: Food Chem., 76, 501 (2002), Rodriguez-Rodriguez, R., et al.: Br. J. Pharmacol., 155, 535 (2008), Sotiroudis, T., et al.: Eur. J. Nutr, 47, 69 (2008),<br></p>

<p>Applications 5β-Cholanic Acid-3α, 6β-Diol is a cholesterol derivative; Plasma lipophilic biomarkers in rats. Also, it is one of two major metabolites from the hydroxylation of hepatic lithocholic acid catalyzed by Cyp3a/Cyp3a11 enzymes in mice.<br>References Mayengbam, S., et al.: Eur. J. Nutr., 55, 1213-1223 (2016); Hrycay, E., et al.: Mol. Cell. Biochem., 389, 119-132 (2014)<br></p>

<p>Applications 7ß-Hydroxycholesterol-d7 is a standard used in the simultaneous measurement of F2-isoprostane, hydroxyoctadecadienoic acid, hydroxyeicosatetraenoic acid, and hydroxycholesterols in plasma and liver of hepatitis patients.<br>References Yoshida, Yasukazu., Analytical Biochemistry, 379, 105-115, (2008)<br></p>

<p>Applications A phytosterol found in canola oil, rapeseed oil, marine algae and shellfish. This compound has been shown to inhibit sterol Δ24-reductase, an enzyme involved in the mammalian cholesterol biosynthesis pathway.<br>References Bishop, G.J., et al.: Plant Cell Physiol. 42, 114, (2001), Fernandez, C., et al., Biochem. J. 366, 109 (2002),<br></p>

<p>Applications (9Z,11E) Methyl Ester 9,11-Octadecadienoic Acid is a fatty acid methyl ester that can be found in olive leaves and in suet oil.<br>References Jiang, J., et al.:Int. J. Mol. Sci., 16, 2864 (2015); Xie, Pu., et al.: Linchan Huaxue Yu Gongye, 34, 97 (2014)<br></p>

<p>Applications Isovaleryl L-Carnitine Chloride is used to prepare carnitine benzyl esters as neuroprotectant prodrugs.<br>References Gong, X., et al.: J. Chem. Res., 6, 327 (2008)<br></p>

<p>Applications Glycolithocholic Acid Sodium Salt is a bile salt and may induce calcium uptake in human erythrocytes.<br>References Oelberg, D.G., et al.: Hepatology, 7 245-52 (1987);<br></p>

<p>Applications (25R)-26-Hydroxy-cholest-4-en-3-one is an oxygenated sterol which has many important biological activities. (25R)-26-Hydroxy-cholest-4-en-3-one has been used as a reactant for the synthesis of other sterols.<br>References Li, S., et. al.: Chem. Phys. Lipids, 99, 33 (1999); Khripach, V., et. al.: Steroids, 70, 551 (2005)<br></p>

<p>Applications 24(R/S)-Hydroxycholesterol-d7 is used in the study of biochemical methods for quantitative detection of steroids containing quantitative charge tags and oxidizing agents and using mass spectroscopy for detection.<br>References Groffoths, Williams., US 20150233953, (2015)<br></p>

<p>Applications It is a potent and selective human CYP2C19 inhibitor.<br>References Suzuki, H., et al.: Drug Metab. Dispos., 30, 235 (2002), Robert, L., et al.: Drug Metab. Dispos., 31, 343 (2003),<br></p>

<p>Applications A labelled metabolite of Cholesterol (C432501).<br>References Marx, J., et al.: Science, 294, 508 (2001), Plosch, T., et al.: J. Biol. Chem., 277, 33870 (2002), Lund, E., et al.: J .Biol. Chem., 278, 22980 (2003),<br></p>

<p>Impurity Ursodeoxycholic Acid EP Impurity D<br>Applications Ursocholic Acid (Ursodeoxycholic Acid EP Impurity D) is an Ursodeoxycholic Acid (U850000) impurity.<br>References Ward, A., et al.: Drugs, 1984, 27, 95 (1984), Sama, C., et al.: Clin. Drug Invest., 13, 192 (1997), Nobilis, M., et al.: J. Pharm. Biomed. Anal., 24, 937 (2001),<br></p>

<p>Impurity Ursodeoxycholic Acid EP Impurity A<br>Applications Chenodeoxycholic Acid (Ursodeoxycholic Acid EP Impurity A) is a major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus facilitates its excretion. Facilitates fat absorption in the small intestine by micellar solubilization of fatty acids and monoglycerides. Anticholelithogenic. Epimeric with Ursodiol.<br>References Danzinger, et al.: N. Engl. J. Med., 286, 1 (1972), Iser, J.H., et al.: Drugs, 21, 90 (1981), Tint, G.S., et al.: Gastroenterology, 91, 1007 (1986),<br></p>

<p>Applications Stabilizer in manufacturing of vinyl polymers; intermediate in synthesis of glycerol, glycidyl ethers, and amines; additive for oil and synthetic hydraulic fluids; epoxy resin diluent.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Hiles, R.A., et al.: Food Cosmet. Toxicol., 19, 347 (1981); Thompson, E.D., et al.: Food Chem. Toxicol., 22, 665 (1984);<br></p>

<p>Stability Air Sensitive<br>Applications (E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylaldehyde (cas# 4206-58-0) is a useful research chemical.<br></p>

<p>Applications Cholesterol (C432501) derivative. Cholesterol is a major component of all biological membranes; ~25% of total brain lipid is Cholesterol. Cholesterol is the principal sterol of the higher animals. Cholesterol was found in all body tissues, especial in the brain, spinal cord, and in animal fats or oils. Cholesterol is the main constituent of gallstones.<br>References Rosin, Z., et al.: Physiol. Chem., 124, 282 (1923), Schoenheimer, et al.: J. Biol. Chem., 105, 355 (1934), Gemant, et al.: Life Sci., 1, 233 (1962), Johnson, K., et al.: 4, 457 (1964),<br></p>

<p>Impurity Estradiol 17?-Hydroxy Impurity; Estradiol EP Impurity B; Ethinylestradiol EP Impurity L<br>Applications Estradiol (known as α-Estradiol or 17 α-Estradiol) is a biologically active estrogen in human breast cancer cells in tissue culture. 17-Εstradiol and its selective receptor, ER-X, are not part of a classical hormone/receptor endocrine system but of a system with important autocrine/paracrine functions in the developing and adult brain(1,2). 17-Estradiol may have enormous implications for hormone replacement strategies at the menopause and in the treatment of such neurodegenerative disorders as Alzheimer’s disease and ischemic stroke(3).This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA). Environmental contaminants; Food contaminants.<br>References 1. Lievertz, R. et al.: J. Obstet. Gynecol. 1987 May;156(5):1289-932. Kuhnz, W. et al.: Arzneimittelforschung. 1993 Sep;43(9):966-73.3. Toran-Allerand, C. et al.: Endocrinology. 2005 Sep;146(9):3843-50.<br></p>