Lipids

<p>Stability Temperature Sensitive. This compound can rearrange to the 1,3-isomer in solutio<br>Applications Activator of phospholipid-dependent protein kinase C; and stimulator of secretion and aggregation in blood platelets.x<br>References Nature, 306, 487 (1983), J. Biol. Chem., 258, 6701 (1983), Biochem. Biophys. Res. Comm., 115, 383 (1983), Benz, I., et al.: J. Membr. Biol., 130, 183 (1992), Haeffner, E.W., et al.: J. Lipid Mediat., 5, 237 (1992), Florin-Christensen, J., et al.: Biochem. J., 289, 783 (1993)<br></p>

<p>Applications An impurity of Griseofulvin (G787500).<br>References Oda, T., et al.: Chem. Pharma. Bull., 34, 858 (1986),<br></p>

<p>Applications (S)-(-)-Canadine is a protoberberine alkaloid which potently block functional KATP channels natively expressed on midbrain dopamine neurons. Canadine is used for treatment of degenerative diseases or conditions associated with KATP channel signaling. (S)-(-)-Canadine has a strong central nervous system-depressing activity and is used in the preparation of tetrahydroprotoberberine derivatives as new antipsychotic agents.<br>References Sun, H. et al.: Bioorg. Med. Chem., 21, 856 (2013); Deeb, O., et al.: Chem. Biol. Drug Des., 76, 255 (2010); Sun., et al.: Br. J. Pharmcol., 158, 1302 (2009); Duchowicz, P., et al.: Bioorg. Med. Chem., 14, 5876 (2006); Yamahara, J. et al.: Chem. Pharm. Bull., 24, 1909 (1976)<br></p>

<p>Applications Campestanol can be used as analyte in biological and analytical studies for the determination of 22 natural brassinosteroids in a minute sample of plant tissue by UHPLC-ESI-MS/MS.<br>References Tarkowska, D., et al.: Anal. Bioanal. Chem., 408, 6799-6812 (2016)<br></p>

<p>Applications α-Hyodeoxycholic Acid is isolated from pig bile. Antitumor agent.<br>References Abadie, C., et al.: Biochem. J., 299, 725 (1994), Taniguchi, T., et al.: J. Biol. Chem., 269, 10071 (1994), Davis, R., et al.: J. Lipid Res., 43, 533 (2002),<br></p>

<p>Stability Light Sensitive<br>Applications cis-7,10,13,16-Docosatetraenoic Acid has been identified as a protein kinase inhibitor, affecting serotonin levels in studies.<br>References Mirnikjoo, B. et al.: J. Biol. Chem., 276, 10888 (2001);<br></p>

<p>Applications Demethyldihydrolanosterol, is a derivative of Lanosterol (L174580). It is also a sterol that activate oocyte meiosis.<br>References Byskov, A., et al.: Nature (London), 374, 559 (1995); Ma, L., et. al.: Food Chem., 139, 503 (2013);<br></p>

<p>Applications A metabolite of Ursodeoxycholic Acid, which is used as an anticholelithogenic.<br></p>

<p>Applications 20(S)-Ginsenoside Rh2 is a bioactive metabolite of the ginsenoside component of Panax ginseng that has been shown to exhibit antibacterial effects in vitro.<br>References Zhang, J. et al.: Eur. J. Pharm., 740, 277 (2014);<br></p>

<p>Stability Hygroscopic<br>Applications (R)-Butyryl Carnitine is a potential prodrug of Carnitine, used for treating seizure disorders.<br>References Fei, Y., et al.: J. Biol. Chem., 275, 23707 (2000), Duran, J., et al.: J. Membr. Biol., 185, 65 (2002), Brown, A., et al.: J. Biol. Chem., 278, 11312 (2003), Gupta, N., et al.: Life Sci., 78, 2419 (2006),<br></p>

<p>Applications Glyceryl Trinonadecanoate is used in the study of Polymorphism and transformation energetics of saturated monoacid triglycerides.<br>References Hagemann, J., et al.: JAOCS, 60, 1123 (1983)<br></p>

<p>Stability Light Sensitive<br>Applications 1,2-Dilinoleoyl-3-palmitoyl-rac-glycerol is a triacylglycerol found in sesame oil.<br>References Lee, D., et al.: Analytica Chimica Acta, 429, 321 (2001); Jahaniaval, F., et al.: J. AM. Oil Chem. Soc., 77,847 (2000)<br></p>

<p>Applications Monolaurin has antibacterial, antiviral, and other antimicrobial effects in vitro.<br>References Li, Q., et al.: Nature, 458, 1034 (2009)<br></p>

<p>Applications One of two major component of bacterial Lipid A .<br>References Jenske, R., et al.: J. Agric. Food Chem., 56, 11578 (2008), Six, D., et al.: Biochem., 47, 8623 (2008),<br></p>

<p>Applications (2α,3β)-2,3-Dihydroxy-urs-12-en-28-oic Acid influences inflammatory gene expression regarding inflammatory bowel disease. In addition, its extracted from the plants Gentiana farreri and shows anti-tumor activity<br>References Mueller, D. et al.: Food Chem., 139, 339 (2013); Thilakarathna, S. et al.: Food Chem., 138, 463 (2013); Yang, A. et al.: Adv. Mat. Res., 554, 1682 (2012);<br></p>

<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 D-erythro-N,N-Dimethylsphingosine is general modulator of protein kinases . D-erythro-N,N-Dimethylsphingosine is implicated in neuropathic pain.<br>References Igarashi, Y. et al.: Biochemistry, 28, 6796 (1989), Igarashi, Y. et al.: J. Biol. Chem., 265, 5385 (1990); Chemical and Engineering News, 90(4) 8 (2012)<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 The 22S-metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.<br>References Samson, M., et al.: J. Biol. Chem., 272, 24934 (1997), Mackay, C., et al.: Nature Immunol., 2, 95 (2001), Navenot, J., et al.: J. Mol. Biol., 313, 1181 (2001),<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>Applications A fat-metabolism stimulator. Antioxidant.<br>References Plotzker, R., et al.: Am. J. Med. Sci., 283, 79 (1982), Evans, J., et al.: Diabetes Technol. Ther., 2, 401 (2000), Konrad, D., et al.: Diabetes, 50, 1464 (2001), Lockhart, B., et al.: Brain Res., 855, 292 (2000),<br></p>

<p>Stability Hygroscopic<br>Applications 3-Methylglutaconic acid is a glutarate which builds up in the urine in 3-methylglutaconic aciduria. 3-methylglutaconic aciduria is a term used to describe five different disorders that impair the functioning of energy-producing centers within cells (mitochondria)<br>References Walsh, R., et al.: J. Inherit. Metab. Dis., 22, 251 (1999); Gonzalez, I., et al.: Am J Med Genet A., 134, 409 (2005); MacKenzie, J., et al.: Biochim Biophys Acta., 1772, 509 (2007)<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 Lanosterol is a sterol cholesterol precursor that maintains a stable concentration in the cortex of rats during aging however concentrations of Lanosterol increases in the liver during aging. Lanosterol is found in Mushroom Inonotus obliquus (I.obliquus) which is known to have anti-inflammatory and anticancer properties.<br>References Smiljanic, K., et. al.: Lipids, 48, 1069 (2013); Ma, L., et. al.: Food Chem., 139, 503 (2013)<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 1,3-Dipalmitoyl-2-oleoyl Glycerol is a triglyceride found in oils from various natural sources such as palm kernels, sunflower seeds and soybean. 1,3-Dipalmitoyl-2-oleoyl Glycerol is used to study the effects of specific synthetic triglycerides on atherosclerosis.<br>References Kritchevsky, D. et al.: LIpids, 35, 621 (2000); Mayamol, P.et al.: J. Food Sci. Technol., 45, 305 (2008);<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>