Lípidos

Applications 1,2-Dimyristoyl-sn-glycero-3-phosphocholine is used in the generation of micelles and liposomes.
References Høyrup, P., et al.: Biochim. Biophys. Acta, 1515, 133 (2001); Heberle, F., et al.: Cold Spring Harb Perspect Biol., 3, 1 (2011)

Applications 5-Cholenic Acid-3β-ol is a bile acid of which the metabolism in humans results in the primary bile acids lithocholic acid and chenodeoxycholic. It is found in hgher concentrations in meconium of premature human babies when compared to full term babies.
References Tohma, M., et al.: Steroids, 44, 47 (1984); Kok, E., et al.: J. Biol. Chem., 256, 6155 (1981); Back, P., et al: Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 354, 83 (1973); Javitt, N., et al.: J. Biol. Chem,, 261, 12486 (1986);

Applications Δ5-Avenasterol is an analog of Stigmasterol (S686750); a plant sterol that is used as a precursor in the synthesis of progesterone.
References Han, P., et al.: Biotechnol. App. Biochem., 54, 105 (2009); Matsunaga, I., et al.: Anal. Biochem., 393, 222 (2009); Huang, C., et al.: Plant Physiol., 150, 1192 (2009)

Applications 1,2-Distearoyl-sn-glycero-3-phospho-rac-(1-glycerol) Sodium Salt is used to prepare polyethyleneglycol-modified liposomal doxorubicin for therapies against drug resistant tumors. It is also used in the PEGylated liposomal drug formulation of the anti-cancer agent oxaliplatin.
References Sugiyama, I., et al.: Int. J. Pharma., 441, 279 (2013); Franzen, U., et al.: Electrophor., 32, 738 (2011)

Applications α-Muricholic Acid is an bile acid found in urine. Studies have linked α-Muricholic in the understanding of the complex signaling pathways of hepatic lipid abnormalities with type 2 diabetes and a treatment target for this condition.
References Haeusier, R.A., et al.: Cell. Metabolism., 15, 65 (2012); Chen, K.H., et al.: Am. J. Physiol., 301, E853 (2011);

Stability Moisture Sensitive
Applications Lecithin has emulsification and lubricant properties, and is a surfactant.
References Shah, D.: J. Colloid and Interface Sci., 37, 744 (1971); Scholfield, C.: J. Am. Oil. Chem. Soc., 58, 889 (1981)

Applications 1,2-Dipalmitoyl-sn-glycerol (1,2-DPG) is an analog of the protein kinase C (PKC)-activating second messenger diacylglycerol. 1,2-Dipalmitoyl-sn-glycerol is a weak activator of PKC.
References Walker, J.M. et al.: J. Biol. Chem., 263, 4537 (1988);

Stability Hygroscopic
Applications rac 1-Oleoyl Glycerol is a monoglyceride. These fatty acid esters are useful for the improvement of texture and flavor of beverages.
References Lee, T.-H., et al.: J. Nat. Prod., 72, 1960 (2009)

Applications Glycolithocholic-2,2,4,4-d4 Acid (CAS# 2044276-16-4) is a useful isotopically labeled research compound.

Applications The 22R-metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.
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),

Applications A fat-metabolism stimulator. Antioxidant.
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),

Stability Hygroscopic
Applications Glycocholic-2,2,4,4-d4 Acid was an analyte found in serum bile acids. Potential application for diagnosis of pediatric liver and intestinal diseases in humans.
References Fu, X., et al.: Clin. Chem. Lab. Med., 58, 787 (2020)

Applications The 22S-metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.
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),

Applications Glycerophospholipids act as regulators of various enzyme activities, and can be used as biological markers to indicate pathological states.
References Perides, G., et al.: J. Biol. Chem., 262, 13742 (1987),

Applications (3β)-3,25-Dihydroxycholest-5-en-7-one is a useful synthetic intermediate in the synthesis of 3β,7α,25-Trihydroxycholest-5-ene (T795075); a potent agonist of GPR183 that induces specific activation of the receptor.
References Antunes, L., et al.: Antimicrob. Agents. Chemtherap., 55, 1494 (2011); Schwarz, M., et al.: J. Cin. Invest., 106, 1175 (2000); Zhang, J., et al.: BIochem. J., 322, 175 (1997)

Applications Ostreasterol is a marine steroid, and also a derivative compound of hydroxycholesterol (H918040), which functions as the main cholesterol elimination product of the brain and was found to be increased in serum of Alzheimer patients.
References Kolsch, H., et al.: J. Neural. Transm., 108, 475 (2001); Gamba, P., et al.: Aging. Cell., 10, 403 (2011); Seet, R.C.S., et al.: Free. Rad. Biol. Med., 48, 560 (2010);

Stability Air and Moisture sensitive
Applications It is used in the production of lipid and fatty acids.
References Cerniglia, C., et al.: J. Bacteriol., 118, 844 (1974), Leahy, J., et al.: Microbiolog. Rev., 54, 305 (1990),

Applications 11-Deoxy-18-hydroxycorticosterone is an analog of Corticosterone (C695700); a glucocorticoid and intermediate in the biosynthesis of Aldosterone (A514700) which is an adrenocortical steroid isolated from the adrenal cortex.
References Schmidt, M., et al.: Endocrinol., 150, 2709 (2009); Bailey, M., et al.: J. Immunol., 182, 7888 (2009); Brunton, P., et al.: J. Neurosci., 29, 6449 (2009); Pruett, S., et al.: Toxicol. Sci., 109, 265 (2009)

Impurity Atorvastatin EP Impurity E
Stability Hygroscopic
Applications (3S,5S)-Atorvastatin Sodium Salt (Atorvastatin EP Impurity E) is a selective, competitive HMG-CoA reductase inhibitor. The only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholesterolemia.
References Kearney, A.S., et al.: Pharm. Res., 10, 1461 (1993), Heinonen, T.M., et al.: Clin. Ther., 18. 853 (1996), Whitfield, L.R., et al.: Eur. J. Drug Metab. Pharmacokinet., 25, 97 (2000)

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

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

Applications 1,2-Dioleoyl-sn-glycero-3-phospho-rac-(1-glycerol) is an analog of 1,2-Dipalmitoyl-sn-glycero-3-phospho-rac-(1-glycerol) (D525495) which forms lipid bilayers. In the high temperature phase, the conformation of the chains is liquid-like. In the low temperature phases, the chains are stiff and parallel and they interdigitate.
References Ranck, J., et al.: Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 488, 432 (1977)

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.
References Tarkowska, D., et al.: Anal. Bioanal. Chem., 408, 6799-6812 (2016)

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

Applications α-Hyodeoxycholic Acid is isolated from pig bile. Antitumor agent.
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),

Applications (4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol is a naturally occurring diterpene that exhibits potent antimicrobial activity.
References Tian, M., et al.: Records of Natural Products, 14, 219 (2020)

Applications A glycidol fatty acid esters in edible oils. An acyl acceptor for the unspecific bifunctional wax ester synthase/acyl-CoA:Diacylglycerol acyltransferase.
References Masukawa, Y. et al.: J. Am. Oil. Chem. Soc., 88, 15 (2011); Kalscheuer, R. et al.: Eur. J. Lipid. Sci. Tech., 105, 578 (2003)

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

Applications Cholesteryl oleate is an esterified form cholesterol found in plasma.

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

Applications D-erythro-N,N-Dimethylsphingosine is general modulator of protein kinases . D-erythro-N,N-Dimethylsphingosine is implicated in neuropathic pain.
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)

Stability Hygroscopic
Applications 1-O-Octadecanoyl-sn-glycerol is a monoacylglycerol (MAG) based saturated fatty acid derivative.
References Garcia, P. et al.: J. Sep. Sci., 34, 999 (2011); Takagi, T. et al.: LIpids, 25, 398 (1990);

Applications Food preservative, having the ability to form complexes with starch, retarding its retrodegradation during storage.
References Yu, S., et al.: J. Agric. Food Chem., 54, 4482 (2006),

Applications 25-Hydroxy Cholesterol-d6, is the labeled analogue of 25-Hydroxy Cholesterol (H918030), which is an oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It also induces apoptosis in human monocytic cell lines as well as inducing apoptosis in CEM cells associated with negative regulation of c-Myc.
References Aupeix, K. et al.: Immunobiology, 194, 415 (1995); Moog, C. et al.: Antivir. Chem, Chemother., 9, 491 (1998); Ayala-Torres, S. et al.: Exp. Cell Res., 246, 193 (1999);

Stability Hygroscopic
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)
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)

Applications 2-Methylenecyclopropaneacetic Acid is an intermediate in the preparation of novel agents for the therapy of non-insulin dependent diabetes mellitus.
References Bell, P., et al.: Bioorg. Med. Chem. Lett., 3, 1007 (1993);

Applications Plant sterol, used as a precursor in the synthesis of progesterone.
References Han, P., et al.: Biotechnol. App. Biochem., 54, 105 (2009), Matsunaga, I., et al.: Anal. Biochem., 393, 222 (2009), Huang, C., et al.: Plant Physiol., 150, 1192 (2009),

Applications 5α-Cholesta-7,24-diene-3β-ol, is the derivative of Zymosterol (Z701520). It can also be used for identification of a new plasma biomarker of Alzheimer's disease using metabolomics technology.
References Sato, Y., et al.: J. Lipid Res., 53, 567 (2012); Schoenheimer, et al.: J. Biol. Chem., 105, 355 (1934);