An isomer of 7-DHC
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8-dehydro Cholesterol

Item No. 25970

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cholesta-5,8-dien-3β-ol
CAS Number
70741-38-7
Molecular Formula
C27H44O
Formula Weight
384.6
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly SolubleMethanol: Slightly Soluble
SMILES
O[C@H](C1)CC[C@@]2(C)C1=CCC3=C2CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@@H](CCCC(C)C)C
InChi Code
InChI=1S/C27H44O/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/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1
InChi Key
VUKORTMHZDZZFR-BXAZICILSA-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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    Product Description

    8-dehydro Cholesterol (8-DHC) is an isomer of the cholesterol precursor 7-DHC (Item No. 14612).1,2,3 It accumulates in tissues and plasma in patients with Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in DHCR7, the gene encoding 3β-hydroxysterol-Δ7-reductase, and decreased cholesterol levels in bodily tissues and fluids, as well as microcephaly, intellectual disability, and distinctive dysmorphic features. 8-DHC levels are increased in serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944 (Item No. 14611).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wolf, C., Chevy, F., Pham, J., et al. Changes in serum sterols of rats treated with 7-dehydrocholesterol-Δ7-reductase inhibitors: Comparison to levels in humans with Smith-Lemli-Opitz syndrome. J. Lipid. Res. 37(6), 1325-1333 (1996).

    2. Björkhem, I., Starck, L., Andersson, U., et al. Oxysterols in the circulation of patients with the Smith-Lemli-Opitz syndrome: Abnormal levels of 24S- and 27-hydroxycholesterol. J. Lipid Res. 42(3), 366-371 (2001).

    3. Griffiths, W.J., Abdel-Khalik, J., Crick, P.J., et al. Sterols and oxysterols in plasma from Smith-Lemli-Opitz syndrome patients. J. Steroid Biochem. Mol. Biol. 169, 77-87 (2017).