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Merck

700066P

Avanti

7-dehydrocholesterol

Avanti Research™ - A Croda Brand

Synonym(s):

7-dehydrocholesterin; Provitamin D3; 110807

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About This Item

Empirical Formula (Hill Notation):
C27H44O
CAS Number:
434-16-2
Molecular Weight:
384.64
MDL number:
MFCD00066680
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

7-dehydrocholesterol, Avanti Research™ - A Croda Brand

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

assay

>99% (TLC)

form

powder

shipped in

dry ice

storage temp.

−70°C

description

Δ,5,7-cholesterol

packaging

pkg of 1 × 5 mg (700066P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

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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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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Biosynthesis of Vitamin D in Skin
Principles of Medical Biology (1997)
Diverse Chemical Scaffolds Enhance Oligodendrocyte Formation by Inhibiting CYP51, TM7SF2, or EBP
Allimuthu D, et al.
Cell Chemical Biology, 26(4), 593-599 (2019)
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
Josi Herron et al.
Current protocols in toxicology, 78(1), e65-e65 (2018-10-16)
Cholesterol and cholesterol-derived oxysterols are critical for embryonic development, synapse formation and function, and myelination, among other biological functions. Indeed, alterations in levels of cholesterol, sterol precursors, and oxysterols result in a variety of developmental disorders, emphasizing the importance of

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