Lipids

Applications A labelled metabolite of Cholesterol (C432501).
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),

Impurity Ursodeoxycholic Acid EP Impurity D
Applications Ursocholic Acid (Ursodeoxycholic Acid EP Impurity D) is an Ursodeoxycholic Acid (U850000) impurity.
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),

Impurity Ursodeoxycholic Acid EP Impurity A
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.
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 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.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Hiles, R.A., et al.: Food Cosmet. Toxicol., 19, 347 (1981); Thompson, E.D., et al.: Food Chem. Toxicol., 22, 665 (1984);

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

Applications 1,2-Dimyristoyl-sn-glycero-3-phospho-rac-(1-glycerol) (Sodium Salt), is used in the production of micelles, liposomes, and other type of artificial membranes.
References Rodrigues, C., et al.: Biophys. Chem, 94, 97 (2001); Van Dijck, P.W., et al.: Biochim. Biophys. Acta., 406, 465 (1975)

Applications Cholesterol 5alpha,6alpha-epoxide is used in the generation of oxysterols and in the studies of the biological significance of oxysterols.
References Lizard, G., et al.: Eur. J. Lipid Sci. Technol., 118, 135 (2016); Sabolova, M., et al.: J. Sci. Food Agric., 97, 5092 (2017); Bezine, M., et al.: Biochimie (2018)

Impurity Estradiol 17?-Hydroxy Impurity; Estradiol EP Impurity B; Ethinylestradiol EP Impurity L
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.
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.

Applications 1,2-Distearoyl-3-oleoyl-rac-glycerol is used in the study of leptin resistance at the blood-brain barrier.
References Banks, W., et al.: Diabetes, 53, 1253 (2004);

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);

Applications Labelled (-)-Norgestrel, an emergency contraceptive. Levonorgestrel is safe, tolerated and effective in emergency contraception in woman.
References Fotherby, K., et al.: J. Steroid Biochem., 19(1C), 817 (1983), Stanczyk, F. Z., et al.: Contraception, 42, 67 (1990), Bednarek, P., et al.: Drugs, 67, 2478 (2007),

Applications A Cholesterol (C432501) metabolite. Lathosterol (indicating cholesterol synthesis) and Sitosterol (indicating cholesterol absorption) also decreased with deteriorating health. Low Lathosterol, Sitosterol (S497050), and Cholesterol (C432501) predicted mortality additively and independently of each other.
References Chyou, P., et al.: Age Ageing, 29, 69 (2000), Schatz, I., et al.: Lancet, 358, 351 (2001), Bjorkman, M., et al.: Eur. J. Endocrinol., 158, 749 (2008),

Applications (+)-cis-Diltiazem-d3 HCl (acetoxy-d3) (CAS# 1217860-13-3) is a useful isotopically labeled research compound.

Applications (25R)-26-Hydroxycholesterol is a desmosterol metabolite that is found in the brain. 26-Hydroxycholesterol has been used as a biomarker for carbon cycling in the northwestern Mediterranean Sea.
References Meljon, A., et. al.: J. Lipid Res., 53, 2469 (2012); Christodoulou, S., et. al.: Marine Chem., 113, 25 (2009)

Applications (S)-Equol and R-Equol are metabolites of the soy isoflavones Daidzein (D103500) and Genistein. Both have significant biological actions.
References Heinonen, S., et al.: Anal. Biochem., 274, 211 (1999), Setchell, K., et al.: J. Nutr., 132, 3577 (2002), Thigpen, J., et al.: Comp. Med., 53, 607 (2003), Yee, S., et al.: Food Chem. Toxicol., 46, 2713 (2008),

Applications 20(S)​-​Ginsenoside Rh1 is an anti-cancer agent found in the leaves of ginseng.
References Zheng, M. et al.: Biomed. Res., 26, 646 (2015);

Applications (+)-20-Hydroxyecdysone regulates gene transcription via a genomic pathway through a transcription complex that is formed.
References Liu, W. et al.: Endocrinol., 155, 1738 (2014); Wang, Q. et al.: Plant Physiol. Biochem., 84, 1 (2014);

Stability Hygroscopic
Applications sn-Glycero-3-phosphocholine-d9 is an isotope labelled analog of sn-Glycero-3-phosphocholine (G598700); a phospholipid and precursor in choline biosynthesis. sn-Glycero-3-phosphocholine is an intermediate in the catabolic pathway of phosphatidylcholine and is used as an nootropic.
References Schmidt, G., et al.: J. Biol. Chem., 161, 523 (1945); Frattola, L., et al.: Curr. Ther. Res., 49, 683 (1991); Olson, D., et al.: Science, 270, 1967 (1995)

Applications A potential inhibitor of glutamate carboxypeptidase.
References Wolcott, T.G., et al.: Biochem. Biophys. Res. Commun., 57, 709 (1974), Knowles, P.F., et al.: Eur. J. Biochem., 114, 139 (1981),

Stability Hygroscopic
Applications Colfosceril Palmitate is a major phospholipid constituent and primary surface tension lowering component of natural lung surfactant. Colfosceril Palmitate is used as pulmonary surfactant and diagnostic aid (fetal lung maturity).
References Cha, S., et al.: J. Biol. Chem., 273, 2153 (1998), Pantusa, M., et al.: Biophys Chem., 114, 121 (2005), Pantusa, M., et al.: Eur. Biophys. J., 37, 961 (2008), Lautenslager, G., et al.: Metabolism, 60, 1683 (2011),

Applications Epoxyeicosatrienoic Acid (EET) has antihypertensive and anti-inflammatory properties and play a role in the maintenance of renal vascular function. N,​N'-​dicyclohexylurea (DCU) increased release of 14,15-EET when the cells were stimulated with a calcium ionophore.Also, it is derived from Arachidonic Acid >97% (A765000), which is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and Arachidonic Acid is also a constituent of animal phosphatides.
References Zhao, X., et al.: J. Am. Soc. Nephrol., 15, 1244 (2004); Fang, X., et al.: J. Biol. Chem., 276, 14867 (2001); Kurosawa, T., et al.: J. Cell. Physiol., 219, 606 (2009); Mazalli, M., et al.: J. Agric. Food Chem., 57, 5028 (2009);

Applications A metabolite of Norgestimate. Note- The oxime isomerizes when: 1) Heated in any solvent or heating the crystalline form 2) Dissolved in MeOH at room temperature very quickly 3) Dissolved in acetone or CHCl3 at room temperature in a couple of hours at room temperature4) In EtOAc or EtOAc/isooctane over a couple of days at RT. It is stable in the crystalline form.
References Phillips, A., et al.: Steroids, 55, 373 (1990)

Applications 1-Palmitoyl-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),

Stability Hygroscopic
Applications 17β-Estradiol 3-O-Sulfate is a neuroactive steroid used in the studies of human recombinant p1 γ-aminobutyric acid type C (GABAC) recptors.
References Li, W.J., et al.: J. Pharmacol. Exp. Therp., 323, 236 (2007); Schneider, C., et al.: Steroids., 69, 245 (2004);

Applications 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 1-Arachidoyl-sn-glycero-3-phosphocholine is a derivative of sn-Glycero-3-phosphocholine (G598700) and can be used as a biomarker in biological studies.
References Tang, C.,et al.: J. Chromatogr. B, 879, 2095 (2011)

Applications 11beta-Hydroxyprogesterone (CAS# 600-57-7) is a useful research chemical compound.

Stability Light Sensitive, Moisture Sensitive
Applications POPE is a component of E. Coli bacteria cell membrane.
References Tu, Y., et al.: Nature Nanotechnology, 8, 594 (2013).

Applications Sphingosine base present in crayfish and drosophila, contributing to muscle degeneration
References Kita, K., et al.: Eur. J. Biochem., 268, 592 (2001), Fyrst, H., et al.: J. Lipid Res., 49, 597 (2008),

Applications 13-Oxyingenol Dodecanoate is a diterpene compound with antinematodal activity. Derivative of Ingenol (I655795), the analogue of Ingenol 3-Angelate (I655800), which has anti-tumor activity when used topically for the treatment of actinic keratosis.
References Shi, J. et al.: Z. Naturforsch. C: J. Biosci., 63, 59 (2008); Ogbourne, S.M., et al.: Cancer. Res., 64, 2833 (2004); Zayed, S.M., et al.: J. Cancer. Res. Clin. Oncol., 127, 40 (2001);

Applications Isoallolithocholic Acid is used as a steroid compound as T regulatory lymphocyte modulators and uses for treatment of inflammatory or autoimmune disorders.
References Littman, D. R., et al.: PCT Int. Appl. 160pp. (2020)

Stability Hygroscopic
Applications L-Propionyl carnitine has been shown to improve the heart's mechanical recovery and other metabolic parameters after ischemia-reperfusion.
References Reznick, A.Z., et al.: Arch. Biochem Biophys., 296, 394 (1992),

Applications (-)-8-Prenylnaringin is a prenylflavonoid, a class on non-steroidal phytoestrogen that mimicks and/or modulating endogenous estrogens via estrogen receptor binding.
References Miyamoto, M. et al.: Planta Med., 64, 516 (1998); Kim, H.J. et al.: Arch. Pharm. Res., 31, 1241 (2008); Zierau, O. et al.: Mol. Cell. Endocrinol., 294, 92 (2008);

Applications A triglyceride for use in making human milk replacements.
References Nakaya, H., et al.: Biotechnology Techniques, 12, 881 (1998), Chen, M., et al.: J. Am. Oil Chemists’ Society, 91, 525 (2004),

Stability Hygroscopic
Applications 12β-Hydroxyisocholic Acid is a bile acid.
References Batta, A.K., et. al.: J. Lipid Res., 32, 977 (1991)

Stability Hygroscopic, Light Sensitive
Applications 1,2-Dioleoyl-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 4β-Hydroxy Cholesterol-d7 is a labelled metabolite of Cholesterol. It is formed from Cholesterol by the drug-metabolizing enzyme cytochrome P 450 3A4. A potential ligand for the nuclear receptor LXR and also a new endogenous CYP3A marker.
References Breuer, O., et al.: J. Lipid Res., 36, 2275 (1995), Pikuleva, I., et al.: J. Biol. Chem., 273, 18153 (1998), Chawla, A., et al.: Science, 294, 1866 (2001), Bodin, K., et al.: J. Biol. Chem., 276, 38685 (2001),

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),