An internal standard for the quantification of 7-dehydro cholesterol
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Unlabeled Version(s)
146127-dehydro Cholesterol
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7-dehydro Cholesterol-d7

Item No. 25969

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cholesta-5,7-dien-25,26,26,26,27,27,27-d7-3β-ol
CAS Number
388622-58-0
Synonyms
  • Δ7-Cholesterol-d7
  • 7-DHC-d7
  • Provitamin D3-d7
Molecular Formula
C27H37D7O
Formula Weight
391.7
Purity
≥99% deuterated forms (d1-d7)
Formulation
A 5 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly solubleMethanol: Slightly soluble (*warmed)
SMILES
O[C@H](C1)CC[C@@]2(C)C1=CC=C3[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@@H](CCCC(C([2H])([2H])[2H])([2H])C([2H])([2H])[2H])C
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $208

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    1 mg

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    Product Description

    7-dehydro Cholesterol-d7 is intended for use as an internal standard for the quantification of 7-dehydro cholesterol (Item No. 14612) by GC- or LC-MS. 7-dehydro Cholesterol (7-DHC) is an immediate precursor of cholesterol.1 It is reduced to cholesterol by the enzyme 3β-hydroxysterol-Δ7-reductase (DHCR7) in the last step of cholesterol biosynthesis. It accumulates in Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in the DHCR7 gene and decreased cholesterol levels in bodily tissues and fluids, as well as microcephaly, intellectual disability, and distinctive dysmorphic features.1,2 7-DHC is highly susceptible to free radical oxidation, giving rise to several oxysterols that may be involved in the pathogenesis of SLOS.1 7-DHC levels are increased in brain, liver, and serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944 (Item No. 14611).1 7-DHC is also a provitamin that is converted to vitamin D3 (Item No. 11792) by ultraviolet-B (UVB) light in a human skin equivalent system and in isolated human skin samples.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Xu, L., Liu, W., Sheflin, L.G., et al. Novel oxysterols observed in tissues and fluids of AY9944-treated rats: A model for Smith-Lemli-Opitz syndrome. J. Lipid Res. 52, 1810-1820 (2011).

    2. Xu, G., Salen, G., Shefer, S., et al. Reproducing abnormal cholesterol biosynthesis as seen in the Smith-Lemli-Opitz syndrome by inhibiting the conversion of 7-dehydrocholesterol to cholesterol in rats. J. Clin. Invest. 95(1), 76-81 (1995).

    3. Lehmann, B., Genehr, T., Knuschke, P., et al. UVB-induced conversion of 7-dehydrocholesterol to 1α,25-dihydroxyvitamin D3 in an in vitro human skin equivalent model. J. Invest. Dermatol. 117(5), 1179-1185 (2001).

    4. Chen, T.C., Chimeh, F., Lu, Z., et al. Factors that influence the cutaneous synthesis and dietary sources of vitamin D. Arch. Biochem. Biophys. 460(2), 213-217 (2007).