An internal standard for the quantification of epicholesterol
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Unlabeled Version(s)
45822Epicholesterol
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Epicholesterol-d6

Item No. 45739

Technical Information
Formal Name
(3α)-cholest-5-en-2,2,3,4,4,6-d6-3-ol
CAS Number
92543-07-2
Synonyms
  • α-Cholesterol-d6
  • 3α-Cholesterol-d6
  • 3-Epicholesterol-d6
Molecular Formula
C27H40D6O
Formula Weight
Purity
≥99% deuterated forms (d1-d6)
A 1 mg/ml solution in ethanol
Ethanol: Soluble
SMILES
O[C@](C1([2H])[2H])([2H])C([2H])([2H])C[C@@]2(C)C1=C([2H])C[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CCCC(C)C
InChi Code
InChI=1S/C27H46O/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/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21-,22+,23-,24+,25+,26+,27-/m1/s1/i9D,13D2,17D2,21D
InChi Key
HVYWMOMLDIMFJA-LPWOMTTRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Epicholesterol-d6 is intended for use as an internal standard for the quantification of epicholesterol by GC- or LC-MS. Epicholesterol is an epimer of cholesterol (Item Nos. 9003100 | 39088 | 39448), where the C-3 hydroxyl group is in the α configuration.1 It has been used to study the stereospecific effects of cholesterol on antibody recognition and receptor function.2,3 Epicholesterol has also been used to study the interactions of cholesterol-containing membranes with stereoisomeric ligands.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tsuchiya, H., and Mizogami, M. Discrimination of stereoisomers by their enantioselective interactions with chiral cholesterol-containing membranes. Molecules 23(1), 49 (2017).

    2. Geva, M., Izhaky, D., Mickus, D.E., et alStereoselective recognition of monolayers of cholesterol, ent-cholesterol, and epicholesterol by an antibody. Chembiochem. 2(4), 265-271 (2001).

    3. Jafurulla, M., Rao, B.D., Sreedevi, S., et alStereospecific requirement of cholesterol in the function of the serotonin1A receptor. Biochim. Biophys. Acta. 1838(1 Pt B), 158-163 (2013).