Lipids

Applications Labelled Chenodiol (Chenodeoxycholic acid). 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. Fcilitates fat absorption in the small intestine by micellar solubilization of fatty acids and monoglycerides. Anticholelithogenic. Epimeric with Ursodiol.
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),

Applications Taurochenodeoxycholic Acid Sodium Salt is a bile acid conjugate and metabolite Taurolithocholic Acid (T009100) with antiinflammatory activity. Taurochenodeoxycholic Acid has been shown to inhibit hepatocyte apoptosis through suppression of Bid translocation to mitochondria.
References Emerman, S. et al.: J. Biol. Chem., 242, 661 (1967); Takikawa, Y. et al.: Falk Symp., 120, 249 (2001); Li, P. et al.: Zhong. Shour. Xue., 28, 1317 (2008);

Stability Hygroscopic
Applications (3α,5β,7α)-7-Hydroxy-3-(sulfooxy)-cholan-24-oic Acid is the 3-monosulfate derivative of chenodeoxycholic acid (C291900), a major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate.
References Haslewood, E.S., et al.: Biochem. J., 155, 401 (1976); Parmentier, G., et al.: Steroids., 30, 583 (1977);

Applications 20-HETE is a cytochrome P450 (CYP450) metabolite that may play an autacoid role in cerebral and renal vasculature.
References McGiff, J.C., et al.: Am J Physiol, 277, R607-R623 (1999);

Stability Hygroscopic
Applications 20(S)-Ginsenoside Rg2 is used as an aldose reductase inhibitor and my exert anti-inflammatory and immunomodulatory activity. It exists as a bioactive metabolite of the ginsenoside component of Panax ginseng.
References Cho, K. et al.: Biomol. Ther., 22, 55 (2014); Fatmawati, S. et al.: Bioorg. Med. Chem. Lett., 24, 4407 (2014);

Applications Omega-3 fatty acid found in marine fish oils and in many phospholipids. Major structural component of excitable membranes of the retina and brain; synthesized in the liver from α-linolenic acid. Nutritional supplement.
References Whitcutt, J.M., et al.: Biochem. J., et al.: 67, 60 (1957), Bazan, N.G., et al.: J. Ocul. Pharmacol., 10, 591 (1994), Makrides, M., et al.: Lipids, 31, 115 (1996),

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

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)

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),

Impurity Ursodeoxycholic Acid EP Impurity F
Applications Nutriacholic Acid (Ursodeoxycholic Acid EP Impurity F) is derivative of Lithocholic Acid (L469180), a cholic acid derivative as TGR5 modulator.
References Schneider, H., et al.: Bioorg. Med. Chem. Lett., 6, 637 (1996); Takamine, F., et al.: Microbiol. Immunol., 39, 11 (1995); Yamashita, H., et al.: Hepatol., 20, 663 (1994);

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 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 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 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 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),

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);

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 1-Palmitoyl-2-oleoyl-3-stearoyl-rac-glycerol is the major triacid triglyceride found in cocoa butter and is used in the improvement of chocolate.
References Sampugna, J. et al.: Lipids, 4, 444 (1969); Padley, F.B. et al.: Rev. Int. Choc., 27, 278 (1972);

Applications Glucocorticoid; an intermediate in the biosynthesis of aldosterone, 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),

Applications Aglicone of saponin dioscin. Diosgenin exists in some food supplements and herbal medicines and lowers plasma cholesterol by increasing fecal cholesterol excretion. It can be converted to Pregnenolone and Progesterone.
References Cayen, M., et al.: J. Lipid Res., 20, 162 (1979), Nervi, F., et al.: J. Clin. Invest., 74, 2226 (1984), Davis, H., et al.: J. Biol. Chem., 279, 33586 (2004), Brown, J., et al.: Biochem. J., 406, 273 (2007),

Applications 2-Stearoyl-rac-glycerol is a biomarker of metabolic responses to hepatotoxicants and carcinogens.
References Broadhurst, D., et al.: Metabolomics, 2, 171 (2006); Shi, J., et al.: Nat. Biotechnol., 25, 930 (2007)

Applications A labelled metabolite of Cholesterol.
References Wang, J., et al.: Biochemistry, 43, 1010 (2004), Lemaire-Ewing, S., et al.: Cell Biol. Toxicol., 21, 97 (2005), Fuda, H., et al.: J. Lipid Res., 48, 1343 ( 2007), Sasaki, H., et al.: Metabolism, 56, 357 (2007),

Applications An oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It 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);

Applications A mineralocorticoid that occurs in adrenal cortex. It acts as a precursor to Aldosterone (A514700).
References Bohl, C., et al.: J. Med.Chem., 47, 3765 (2004), Smith, J., et al.: Steroids, 73, 1160 (2008),

Applications 3-Hydroxy-7,12-diketocholanoic Acid is a bile acid salt as biosurfactants.
References Posa, M., et al.: Steroids, 86, 16-25 (2014)

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 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 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)

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),

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 (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);