An internal standard for the quantification of 25-hydroxy cholesterol
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Alternative(s)
4482825-hydroxy Cholesterol-d2
Unlabeled Version(s)
1109725-hydroxy Cholesterol
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25-hydroxy Cholesterol-d6

Item No. 11099

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cholest-5-ene-26,26,26,27,27,27-d6-3β,25-diol
CAS Number
88247-69-2
Molecular Formula
C27H40D6O2
Formula Weight
408.7
Purity
≥99% deuterated forms (d1-d6)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 100 µg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2) (1:2): 500 µg/ml
SMILES
O[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CCCC(C([2H])([2H])[2H])(O)C([2H])([2H])[2H]
InChi Code
InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1/i2D3,3D3
InChi Key
INBGSXNNRGWLJU-KHKDDIDZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $70

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    1 mg

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    5 mg

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    Product Description

    25-hydroxy Cholesterol-d6 is intended for use as an internal standard for the quantification of 25-hydroxy cholesterol (Item No. 11097) by GC- or LC-MS. 25-hydroxy Cholesterol is an oxysterol.1 It is formed from cholesterol by cholesterol-25-hydroxylase, and its production can be induced by inflammation or infection.2 25-hydroxy Cholesterol suppresses endogenous cholesterol synthesis by binding to insulin-induced gene (INSIG) proteins and preventing sterol regulatory element binding proteins (SREBPs) from being transported to the Golgi. It inhibits IgA class switching induced by LPS and various cytokines in B cells (IC50 = ~50 nM).3 25-hydroxy Cholesterol inhibits replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Vero cells (EC50 = 3.675 µM) and reduces increases in viral protein production in infected Vero cells when used prior to infection.4 It reduces viral RNA loads in the lung and trachea in a mouse model of SARS-CoV-2 infection when administered at a dose of 100 mg/kg per day. Serum levels of 25-hydroxy cholesterol are increased in patients with SARS-CoV-2.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Adams, C.M., Reitz, J., De Brabander, J.K., et al. Cholesterol and 25-hydroxycholesterol inhibit activation of SREBPs by different mechanisms, both involving SCAP and Insigs. The Journal of Biological Chemisty 279(50), 52772-52780 (2004).

    2. Cystger, J.G., Dang, E.V., Reboldi, A., et al. 25-Hydroxycholesterols in innate and adaptive immunity. Nat. Rev. Immunol. 14(11), 731-743 (2014).

    3. Bauman, D.R., Bitmansour, A.D., McDonald, J.G., et al. 25-Hydroxycholesterol secreted by macrophages in response to toll-like receptor activation suppresses immunoglobulin A production. Proc. Natl. Acad. Sci. USA 106(39), 16764-16769 (2009).

    4. Zu, S., Deng, Y.-Q., Zhou, C., et al. 25-Hydroxycholesterol is a potent SARS-CoV-2 inhibitor. Cell Res. 30(11), 1043-1045 (2020).

    5. Asano, T., Wakabayashi, T., Kondo, Y., et al. Serum 25-hydroxycholesterol levels are increased in patients with coronavirus disease 2019. J. Clin. Lipidol. 17(1), 78-86 (2023).