An active metabolite of cholesterol
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7β,25-dihydroxy Cholesterol

Item No. 43245

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cholest-5-ene-3β,7β,25-triol
CAS Number
64907-21-7
Molecular Formula
C27H46O3
Formula Weight
418.7
Purity
≥98%
Formulation (Request formulation change)
A solid
SMILES
O[C@H](C1)CC[C@@]2(C)C1=C[C@H](O)[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CCCC(C)(O)C
InChi Code
InChI=1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23+,24+,26+,27-/m1/s1
InChi Key
BQMSKLCEWBSPPY-CGSQRZAOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $164

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    1 mg

    $312

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    5 mg

    $740

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    10 mg

    $1,066

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    Product Description

    7β,25-dihydroxy Cholesterol is an active metabolite of cholesterol (Item Nos. 9003100 | 39088 | 39448).1 It is formed from cholesterol via 7-keto,25-hydroxy cholesterol (Item No. 25973) or 7β-hydroxy cholesterol (Item No. 20099) intermediates by 11β-hydroxysteroid dehydrogenase (11β-HSD) or cholesterol 25-hydroxylase (CH25H), respectively. 7β,25-dihydroxy Cholesterol activates Epstein-Barr virus-induced G protein-coupled receptor 2 (EBI2), also known as GPR183, in a GTPγS assay (EC50 = 221 nM) but does not bind to EBI2 in CHO cell membranes expressing the human receptor in a radioligand binding assay (IC50 = 2,632 nM).2 Unlike 7α,25-dihydroxy cholesterol (Item No. 11032), it does not induce migration of isolated mouse splenocytes when used at concentrations up to 100 nM.3 7β,25-dihydroxy Cholesterol acts as a cellular chaperone that corrects the localization defect of Niemann-Pick disease type C intracellular cholesterol transporter 1 containing an isoleucine-to-threonine substitution at position 1061 (NPC1I1061T) in HEK293 cells expressing the mutant transporter (EC50 = 1.9 µM).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Beck, K.R., Kanagaratnam, S., Kratschmar, D.V., et al. Enzymatic interconversion of the oxysterols 7β,25-dihydroxycholesterol and 7-keto,25-hydroxycholesterol by 11β-hydroxysteroid dehydrogenase type 1 and 2. J. Steroid Biochem. Mol. Biol. 190, 19-28 (2019).

    2. Hannedouche, S., Zhang, J., Yi, T., et al. Oxysterols direct immune cell migration via EBI2. Nature 475(7357), 524-527 (2011).

    3. Liu, C., Yang, X.V., Wu, J., et al. Oxysterols direct B-cell migration through EB12. Nature 475(7357), 519-523 (2011).

    4. Ohgane, K., Karaki, F., Noguchi-Yachide, T., et al. Structure-activity relationships of oxysterol-derived pharmacological chaperones for Niemann-Pick type C1 protein. Bioorg. Med. Chem. Lett. 24(15), 3480-3485 (2014).