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700116P

Avanti

7-dehydrocholesterol-d7

7-dehydrocholesterol-d7, powder

Synonym(s):

111110

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About This Item

Empirical Formula (Hill Notation):
C27H37D7O
CAS Number:
388622-58-0
Molecular Weight:
391.68
MDL number:
MFCD22570234
UNSPSC Code:
41141804
NACRES:
NA.25

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

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

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.

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).

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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
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
Anika V Prabhu et al.
The Journal of biological chemistry, 291(16), 8363-8373 (2016-02-19)
Cholesterol is detrimental to human health in excess but is also essential for normal embryogenesis. Hence, enzymes involved in its synthesis possess many layers of regulation to achieve balanced cholesterol levels. 7-Dehydrocholesterol reductase (DHCR7) is the terminal enzyme of cholesterol
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