An epimer of cholesterol
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Product Categories

Product Type

Biochemicals
Lipids
Sterol Lipids

Research Area

Lipid Biochemistry
Sterol Lipids

Epicholesterol

Item No. 45822

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3α)-cholest-5-en-3-ol
CAS Number
474-77-1
Synonyms
  • α-Cholesterol
  • 3α-Cholesterol
  • 3-Epicholesterol
Molecular Formula
C27H46O
Formula Weight
386.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Ethanol: Slightly soluble: 0.1-1 mg/ml
SMILES
C[C@@]12[C@](CC[C@]2([H])[C@H](C)CCCC(C)C)([H])[C@@]3([H])[C@@](CC1)([H])[C@@]4(C(C[C@@H](CC4)O)=CC3)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
InChi Key
HVYWMOMLDIMFJA-VEIPTCAHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

    $400

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    25 mg

    $823

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    Product Description

    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 al. Stereoselective 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 al. Stereospecific requirement of cholesterol in the function of the serotonin1A receptor. Biochim. Biophys. Acta. 1838(1 Pt B), 158-163 (2013).