313-04-2 Usage
Description
Desmosterol is a cholestanoid that is cholesta-5,24-diene substituted by a beta-hydroxy group at position 3. It is an intermediate metabolite obtained during the synthesis of cholesterol and lacks a double bond between C24 and C25 compared to cholesterol. It is present in the membrane of spermatozoa and astrocytes and is the major brain sterol. Desmosterol is an off-white solid and has been used in various applications due to its unique properties.
Uses
Used in Cellular Membrane Studies:
Desmosterol is used as a cholesterol substitute in cellular membrane studies. It helps researchers understand the role of cholesterol in cellular membranes and its effects on cell function.
Used in Cholesterol Biosynthesis Research:
As an immediate precursor to cholesterol in the Bloch pathway of cholesterol biosynthesis, desmosterol is used to study the process of cholesterol synthesis and its regulation.
Used in Human Protein Interaction Studies:
Desmosterol has been used as a sterol to test its interaction with human protein Mincle, providing insights into the molecular interactions involving this protein.
Used in Analytical Chemistry:
Desmosterol is used as an internal standard in ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) for accurate and precise quantification of related compounds.
Used in Lipid Monolayer Preparation:
Desmosterol may be used in the preparation of lipid monolayers, which are essential for studying the properties and behavior of lipids in biological membranes.
Used in Brain Development Research:
During brain development, desmosterol transiently accumulates, composing up to 30% of total brain sterol. It is poised to rapidly enrich membrane sterols, making it an important molecule for studying brain development and related conditions.
Used in Atherosclerosis Research:
24-dehydro Cholesterol, a related compound, has been reported to activate liver X receptor-target genes in both the liver of cholesterol-free mice and in cholesterol-starved macrophage foam cells in atherosclerotic lesions. This makes desmosterol a potential molecule of interest in atherosclerosis research.
Used in Desmosterolosis Research:
Desmosterolosis is a condition resulting from defects in cholesterol synthesis, leading to an accumulation of excess 24-dehydro cholesterol. Desmosterol is used in the study of this condition to understand its underlying mechanisms and potential treatments.
Biochem/physiol Actions
Desmosterol is a precursor of cholesterol in the Bloch pathway and the enzyme 24-dehydrocholesterol reductase catalyzes this step. Desmosterol accumulates during impairment of 24-dehydrocholesterol reductase enzyme thereby leading to desmosterolosis. Desmosterol is a liver X receptor (LXR) agonist . It is a potential therapeutic target for treating the neurodegenerative disorder. Desmosterol regulates inflammatory signaling in macrophages.
Check Digit Verification of cas no
The CAS Registry Mumber 313-04-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,1 and 3 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 313-04:
(5*3)+(4*1)+(3*3)+(2*0)+(1*4)=32
32 % 10 = 2
So 313-04-2 is a valid CAS Registry Number.
InChI:InChI=1/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
313-04-2Relevant articles and documents
Hartmann et al.
, p. 3003,3005 (1972)
A new highly stereoselective synthesis of cerebrosterol, an agonist of the nuclear receptor LXRs
Zhou, Xiang-Dong,Zhou, Wei-Shan
, p. 8291 - 8296 (2001)
The title compound, cerebrosterol 1, was synthesized stereoselectively (97% d.e.) in 41% overall yield from methyl hyodeoxycholanate 2 in 10 steps with desmosterol acetate 8 as the key intermediate and the modified Sharpless asymmetric dihydroxylation as the key step.
-
Bergmann,Dusza
, p. 459 (1958)
-
Stereocontrolled syntheses of 24(S),25-epoxycholesterol and related oxysterols for studies on the activation of LXR receptors
Corey,Grogan, Michael J.
, p. 9351 - 9354 (2007/10/03)
Efficient syntheses are described of desmosterol (4), the corresponding 24(S),25 epoxide (6) and various analogs of 6 for evaluation as ligands and functional activators of LXR receptors.
