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1-O-Oleyl-rac-glycerol (CAS 111-03-5)

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Alternate Names:
Monoolein
Application:
1-O-Oleyl-rac-glycerol is a surfactant, releases free glycerol and oleic acid upon hydrolysis
CAS Number:
111-03-5
Molecular Weight:
356.5
Molecular Formula:
C21H40O4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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1-O-Oleyl-rac-glycerol is a chemical used primarily in lipid research studies. It is a monoacylglycerol that contains an oleyl group, which is an unsaturated fatty acid chain, esterified to the glycerol backbone. This compound is of particular interest in the study of lipid metabolism and signaling pathways. Researchers use 1-O-Oleyl-rac-glycerol to investigate the role of monoacylglycerols in biological membranes and their function as intermediates in the biosynthesis and degradation of triglycerides and phospholipids. Additionally, this molecule is relevant in the examination of lipid signaling, as monoacylglycerols can serve as second messengers in cellular communication processes. In studies of digestion and absorption of dietary fats, 1-O-Oleyl-rac-glycerol is utilized to model the breakdown products of dietary triglycerides. Its behavior in biological systems helps to understand the enzymatic processes involved in lipid digestion and the subsequent uptake by intestinal cells.


1-O-Oleyl-rac-glycerol (CAS 111-03-5) References

  1. Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior.  |  Caboi, F., et al. 2001. Chem Phys Lipids. 109: 47-62. PMID: 11163344
  2. Induction of 5-lipoxygenase activation in polymorphonuclear leukocytes by 1-oleoyl-2-acetylglycerol.  |  Albert, D., et al. 2003. Biochim Biophys Acta. 1631: 85-93. PMID: 12573453
  3. 1-Oleoyl-2-acetylglycerol stimulates 5-lipoxygenase activity via a putative (phospho)lipid binding site within the N-terminal C2-like domain.  |  Hörnig, C., et al. 2005. J Biol Chem. 280: 26913-21. PMID: 15923196
  4. Regulation of 5-lipoxygenase enzyme activity.  |  Rådmark, O. and Samuelsson, B. 2005. Biochem Biophys Res Commun. 338: 102-10. PMID: 16122704
  5. The role of diacylglyceride generation by phospholipase D and phosphatidic acid phosphatase in the activation of 5-lipoxygenase in polymorphonuclear leukocytes.  |  Albert, D., et al. 2008. J Leukoc Biol. 83: 1019-27. PMID: 18218859
  6. Mixed-emulsifier stabilised emulsions: Investigation of the effect of monoolein and hydrophilic silica particle mixtures on the stability against coalescence.  |  Pichot, R., et al. 2009. J Colloid Interface Sci. 329: 284-91. PMID: 18977494
  7. Assessment of the percutaneous penetration of cisplatin: the effect of monoolein and the drug skin penetration pathway.  |  Simonetti, LD., et al. 2009. Eur J Pharm Biopharm. 73: 90-4. PMID: 19442727
  8. Orientation and specific interactions of nucleotides and nucleolipids inside monoolein-based liquid crystals.  |  Murgia, S., et al. 2009. J Phys Chem B. 113: 9205-15. PMID: 19569723
  9. 5-Lipoxygenase, a key enzyme for leukotriene biosynthesis in health and disease.  |  Rådmark, O., et al. 2015. Biochim Biophys Acta. 1851: 331-9. PMID: 25152163
  10. Substrate specificity of O-alkylglycerol monooxygenase (E.C. 1.14.16.5), solubilized from rat liver microsomes.  |  Kötting, J., et al. 1987. Lipids. 22: 831-5. PMID: 3444374

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

1-O-Oleyl-rac-glycerol, 1 g

sc-201999
1 g
$295.00