Cholesterol-d6

Names

[ Name ]:
Cholesterol-d6

[Synonym ]:
4,6-Diamino-2-<2-nitro-phenyl>-1,3,5-triazin
<26,27-2H6>cholesterol
D6-cholesterol
2-o-Nitrophenyl-4,6-diamino-s-triazin

Biological Activity

[Description]:

Cholesterol-d6 is the deuterium labeled Cholesterol. Cholesterol is the major sterol in mammals and is makes up 20-25% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3][4].

[Related Catalog]:

Signaling Pathways >> Others >> Estrogen Receptor/ERR

[In Vitro]

Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs[1].

[References]

[1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53(2):211-216.

[2]. Casaburi I, et al. Cholesterol as an Endogenous ERRα Agonist: A New Perspective to Cancer Treatment. Front Endocrinol (Lausanne). 2018 Sep 11;9:525.

[3]. Dietschy JM, et al. Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97.

[4]. Fukui K, et al. Effect of Cholesterol Reduction on Receptor Signaling in Neurons. J Biol Chem. 2015 Sep 14.

Chemical & Physical Properties

[ Density]:
1.003 g/cm3

[ Boiling Point ]:
360ºC

[ Melting Point ]:
147-149ºC

[ Molecular Formula ]:
C₂₇H₄₀D₆O

[ Molecular Weight ]:
392.69

[ Flash Point ]:
209.291ºC

[ Exact Mass ]:
392.39300

[ PSA ]:
20.23000

[ LogP ]:
7.38870

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

PtdIns4P synthesis by PI4KIIIα at the plasma membrane and its impact on plasma membrane identity.

J. Cell Biol. 199 , 1003-16, (2012)

Plasma membrane phosphatidylinositol (PI) 4-phosphate (PtdIns4P) has critical functions via both direct interactions and metabolic conversion to PI 4,5-bisphosphate (PtdIns(4,5)P₂) and other downstrea...