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700116P

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7-dehydrocholesterol-d7

7-dehydrocholesterol-d7, powder

Synonym(e):

111110

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About This Item

Empirische Formel (Hill-System):
C27H37D7O
CAS-Nummer:
388622-58-0
Molekulargewicht:
391.68
MDL-Nummer:
MFCD22570234
UNSPSC-Code:
41141804
NACRES:
NA.25

Assay

>99% (TLC)

Form

powder

Verpackung

pkg of 1 × 1 mg (700116P-1mg)

Hersteller/Markenname

Avanti Research™ - A Croda Brand 700116P

Versandbedingung

dry ice

Lagertemp.

−70°C

SMILES String

O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@@H](CC[C@@H]4[C@@H](CCCC(C([2H])([2H])[2H])(C([2H])([2H])[2H])[2H])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/t19-,21+,23-,24+,25+,26+,27-/m1/s1/i1D3,2D3,18D

InChIKey

UCTLRSWJYQTBFZ-UDEPUTHCSA-N

Allgemeine Beschreibung

7-dehydrocholesterol (7-DHC) is a cholesterol precursor and is localized in basal epidermal keratinocytes. 7DHC on photolysis in the presence of ultraviolet light B generates previtamin D3. The enzyme 7-dehydrocholesterol reductase (DHCR7) catalyzes the reduction of C(7-8) double bond of 7-DHC to cholesterol. 7-dehydrocholesterol-d7 is a deuterated derivative of 7-dehydrocholesterol.

Anwendung

7-dehydrocholesterol-d7 has been used:
  • as an internal standard: to spike Chlamydomonas CC-125 lipid extract for mass spectroscopy analysis
  • in liquid chromatography–mass spectrometry (LC-MS) for cultured cells oxysterol analysis
  • to treat and label SRD-1 cell (chinese hamster ovary (CHO) mutant cell-line) for gas chromatography/mass spectrometry (GC/MS) analysis

Biochem./physiol. Wirkung

7-Dehydrocholesterol (7-DHC) is used as a precursor for microbial vitamin D3 production. Impairment of 7-dehydrocholesterol reductase (DHCR7) functionality leads to 7-DHC accumulation and is implicated in Smith-Lemli-Opitz syndrome (SLOS).

Verpackung

5 mL Amber Glass Screw Cap Vial (700116P-1mg)

Rechtliche Hinweise

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

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Analysenzertifikate (COA)

Lot/Batch Number

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Andrzej T Slominski et al.
PloS one, 4(2), e4309-e4309 (2009-02-05)
Since P450scc transforms 7-dehydrocholesterol (7DHC) to 7-dehydropregnenolone (7DHP) in vitro, we investigated sequential 7DHC metabolism by adrenal glands ex vivo. There was a rapid, time- and dose-dependent metabolism of 7DHC by adrenals from rats, pigs, rabbits and dogs with production
Hanul Kim et al.
Frontiers in microbiology, 6, 54-54 (2015-03-12)
Concern about global warming has prompted an intense interest in developing economical methods of producing biofuels. Microalgae provide a promising platform for biofuel production, because they accumulate high levels of lipids, and do not compete with food or feed sources.
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
Hisako Akiyama et al.
Journal of lipid research, 57(11), 2061-2072 (2016-11-03)
To date, sterylglucosides have been reported to be present in various fungi, plants, and animals. In bacteria, such as Helicobacter pylori, proton NMR spectral analysis of isolated 1-O-cholesteryl-β-d-glucopyranoside (GlcChol) demonstrated the presence of an α-glucosidic linkage. By contrast, in animals
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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