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18:1 Cholesterol-[d7]

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Category Standards
Catalog NO. BPG-3139
Product Name 18:1 Cholesterol-[d7]
CAS 2260669-48-3
Molecular Formula C45H71D7O2
Molecular Weight 658.14
18:1 Cholesterol-[d7]
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Product Information

Description This deuterium labelled lipid is also available in a formulation of multiple lipid standards.
Synonyms cholest-5-en-3b-yl oleate-d7; 18:1-d7-cholesterol; Cholesteryl Oleate-d7; Oleoylcholesterol-d7; Cholesterol Oleate-d7; Cholesteryl cis-9-octadecenoate-d7; Cholest-5-en-3-beta-yl oleate-d7; Oleic acid cholesteryl ester-d7; 18:1 Cholesteryl ester-d7; CE(18:1)-d7
IUPAC Name (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl (Z)-octadec-9-enoate-16,16,17,17,18,18,18-d7
Purity >99%
Solubility Soluble in Chloroform (Slightly), Ethyl Acetate (Slightly)
Related CAS 303-43-5 (unlabelled)
Appearance Off-white Solid
Shelf Life 1 Year
Storage Store at -20°C under inert atmosphere
Exact Mass 657.644
Hygroscopic Yes
Light Sensitive No
Percent Composition C 82.12%, H 13.02%, O 4.86%

1. Study of Lipid Membrane Dynamics: 18:1 Cholesterol-[d7] is a deuterium-labeled variant of cholesterol that is extensively used in the study of lipid membrane dynamics. The incorporation of deuterium atoms allows for the detailed analysis of cholesterol’s behavior within lipid bilayers using techniques such as nuclear magnetic resonance (NMR) spectroscopy and neutron scattering. These tools can provide insights into the organization, fluidity, and phase behavior of lipid membranes, which are critical for understanding how cellular membranes function. By substituting hydrogen atoms with deuterium, researchers can trace the movement and interaction of cholesterol in various lipid environments more precisely.

2. Biomedical Research and Drug Development: In the realm of biomedical research and drug development, 18:1 Cholesterol-[d7] plays a pivotal role, particularly in examining how cholesterol influences the efficacy and mechanism of action of therapeutic agents. Cholesterol is a fundamental component of cell membranes, influencing membrane permeability and cellular signaling. By using deuterium-labeled cholesterol, researchers can monitor its distribution and interaction with pharmaceuticals at a molecular level. This information is crucial for developing drugs targeting cholesterol-related pathways or for understanding how lipid environments affect drug delivery systems, ensuring better therapeutic outcomes.

3. Metabolic Pathway Studies: 18:1 Cholesterol-[d7] is a valuable tool in tracing metabolic pathways involving cholesterol. Its isotopic labeling allows researchers to distinguish between endogenous cholesterol and externally added, labeled cholesterol in metabolic studies. This is particularly important in research focused on disorders such as cardiovascular diseases, where cholesterol metabolism plays a critical role. By tracking the incorporation and conversion of labeled cholesterol, scientists can gain insights into the efficiency and regulation of cholesterol metabolism under various physiological and pathological conditions, aiding in the development of better diagnostic and therapeutic strategies.

4. Structural Biology and Molecular Simulations: In the field of structural biology and molecular simulations, 18:1 Cholesterol-[d7] is used to build accurate models of lipid bilayers and protein-lipid interactions. The detailed structural data obtained from experiments involving deuterium-labeled molecules inform computational models and simulations, enhancing their accuracy. These models are instrumental in elucidating the complex interactions between cholesterol and membrane proteins, which can influence protein function and membrane integrity. Understanding these interactions at a high resolution is crucial for designing interventions that target membrane-associated diseases or for developing biomimetic materials and nanotechnology applications.

References 1. Feltes M, Moores S, Gale SE, Krishnan K, Mydock-McGrane L, Covey DF, Ory DS, Schaffer JE. Synthesis and characterization of diazirine alkyne probes for the study of intracellular cholesterol trafficking. J Lipid Res. 2019 Mar;60(3):707-716. doi: 10.1194/jlr.D091470. Epub 2019 Jan 7. PubMed ID: 30617147.
2. Feltes M, Moores S, Gale SE, Krishnan K, Mydock-McGrane L, Covey DF, Ory DS, Schaffer JE. Synthesis and characterization of diazirine alkyne probes for the study of intracellular cholesterol trafficking. J Lipid Res. 2019 Jan 7. pii: jlr.D091470. doi: 10.1194/jlr.D091470. [Epub ahead of print]. ...PubMed ID: 30617147.

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