An internal standard for the quantification of 25-hydroxy cholesterol
Related Products
Alternative(s)
1109925-hydroxy Cholesterol-d6
Unlabeled Version(s)
1109725-hydroxy Cholesterol
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25-hydroxy Cholesterol-d2

Item No. 44828

Product Insert (PDF)
Technical Information
Formal Name
(3S,8S,9S,10R,13R,14S,17R)-17-((R)-6-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-7,7-d2-3-ol
Molecular Formula
C27H44D2O2
Formula Weight
404.7
Purity
≥99% deuterated forms (d1-d2)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Soluble: ≥10 mg/mlMethanol: Sparingly soluble: 1-10 mg/ml
SMILES
[H][C@]12[C@]([H])(CC[C@]3([C@]2(CC[C@]3([H])[C@@H](CCCC(C)(O)C)C)[H])C)[C@@]4(C)CC[C@@H](CC4=CC1([2H])[2H])O
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/i9D2
InChi Key
INBGSXNNRGWLJU-HACJLSAASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $63

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    1 mg

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    5 mg

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    Product Description

    25-hydroxy Cholesterol-d2 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).