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About This Item
Empirical Formula (Hill Notation):
C27H37D7O
CAS Number:
Molecular Weight:
391.68
MDL number:
UNSPSC Code:
41141804
NACRES:
NA.25
Product Name
7-dehydrocholesterol-d7, 7-dehydrocholesterol-d7, powder
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
InChI key
UCTLRSWJYQTBFZ-UDEPUTHCSA-N
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (700116P-1mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 700116P
shipped in
dry ice
storage temp.
−70°C
Application
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 Actions
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).
General description
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.
Packaging
5 mL Amber Glass Screw Cap Vial (700116P-1mg)
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
Regulatory Information
美国出口管控产品
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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.
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
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
Xiao-Jing Guo et al.
Biotechnology for biofuels, 11, 192-192 (2018-07-22)
7-Dehydrocholesterol (7-DHC) has attracted increasing attentions due to its great medical value and the enlarging market demand of its ultraviolet-catalyzed product vitamin D3. Microbial production of 7-DHC from simple carbon has been recognized as an attractive complement to the traditional
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
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