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About This Item
Empirical Formula (Hill Notation):
C27H44O
CAS Number:
Molecular Weight:
384.64
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
Product Name
7-dehydrocholesterol, Δ,5,7-cholesterol, powder
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 5 mg (700066P-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 700066P
shipped in
dry ice
storage temp.
−70°C
SMILES string
OC1CCC2(C3CCC4(C(CCC4C(CCCC(C)C)C)C3=CC=C2C1)C)C
InChI
1S/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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3
InChI key
UCTLRSWJYQTBFZ-UHFFFAOYSA-N
General description
7-dehydrocholesterol is a metabolite produced in cholesterol synthesis. It is an unsaturated sterol predominantly found in the epidermis.
Application
7-dehydrocholesterol has been used:
- in gas chromatography/mass spectrometry (GC/MS)-based sterol profiling to quantify 7-dehydrocholesterol in oligodendrocyte progenitor cells (OPCs)
- as an internal standard for the analysis of sterols and oxysterols using ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS)
- as an internal standard for lipid measurements by liquid chromatography (LC)-MS
Biochem/physiol Actions
7-dehydrocholesterol acts as a precursor of vitamin D3 under the conditions of high temperature and ultraviolet (UV) light.
Packaging
5 mL Amber Glass Screw Cap Vial (700066P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Biosynthesis of Vitamin D in Skin
Principles of Medical Biology (1997)
Metabolic Precursor of Cholesterol Causes Formation of Chained Aggregates of Liquid-Ordered Domains.
Galya Staneva et al.
Langmuir : the ACS journal of surfaces and colloids, 32(6), 1591-1600 (2016-01-20)
7-Dehydrocholesterol, an immediate metabolic predecessor of cholesterol, can accumulate in tissues due to some metabolic abnormalities, causing an array of symptoms known as Smith-Lemli-Opitz syndrome. Enrichment of cellular membranes with 7-dehydrocholesterol interferes with normal cell-signaling processes, which involve interaction between
Peng He et al.
Biomacromolecules, 6(5), 2455-2457 (2005-09-13)
These studies show that single-walled carbon nanotubes (SWNTs) can be effectively modified using phospholipids. Using a simple surface modification of SWNTs, followed by deposition of 1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3-phosphoethanolamine (DCPE) phosphipid, results in stable water-dispersible SWNTs with highly uniform thickness.
Diverse Chemical Scaffolds Enhance Oligodendrocyte Formation by Inhibiting CYP51, TM7SF2, or EBP
Allimuthu D, et al.
Cell Chemical Biology, 26(4), 593-599 (2019)
Devanand K Shenoy et al.
Nano letters, 5(6), 1181-1185 (2005-06-10)
We demonstrate that polymerizable planar membranes permit reconstitution of protein ion channels formed by the bacterial toxins Staphylococcus aureus alpha-hemolysin (alphaHL) and Bacillus anthracis protective antigen 63. The alphaHL channel remained functional even after membrane polymerization. Surface pressure measurements suggest
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