An immediate precursor to cholesterol
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7-dehydro Cholesterol

Item No. 14612

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cholesta-5,7-dien-3β-ol
CAS Number
434-16-2
Synonyms
  • Δ7-Cholesterol
  • 7-DHC
  • NSC 18159
  • Provitamin D3
Molecular Formula
C27H44O
Formula Weight
384.6
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 0.1 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
λmax
271, 282, 293 nm
SMILES
CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C
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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1
InChi Key
UCTLRSWJYQTBFZ-DDPQNLDTSA-N
Origin
Animal/Wool
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

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    Product Description

    7-dehydro Cholesterol (7-DHC) is an immediate precursor of cholesterol.1 It is reduced to cholesterol by the enzyme 3β-hydroxysterol-Δ7-reductase (DHCR7) in the last step of cholesterol biosynthesis. 7-DHC accumulates in Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in the DHCR7 gene and decreased cholesterol levels in bodily tissues and fluids, as well as microcephaly, intellectual disability, and distinctive dysmorphic features.1,2 It is highly susceptible to free radical oxidation, giving rise to several oxysterols that may be involved in the pathogenesis of SLOS.1 7-DHC levels are increased in brain, liver, and serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944 (Item No. 14611).1 7-DHC is a provitamin that is converted to vitamin D3 (Item No. 11792) by ultraviolet-B (UVB) light in a human skin equivalent system and in isolated human skin samples.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Xu, L., Liu, W., Sheflin, L.G., et al. Novel oxysterols observed in tissues and fluids of AY9944-treated rats: A model for Smith-Lemli-Opitz syndrome. J. Lipid Res. 52, 1810-1820 (2011).

    2. Xu, G., Salen, G., Shefer, S., et al. Reproducing abnormal cholesterol biosynthesis as seen in the Smith-Lemli-Opitz syndrome by inhibiting the conversion of 7-dehydrocholesterol to cholesterol in rats. J. Clin. Invest. 95(1), 76-81 (1995).

    3. Lehmann, B., Genehr, T., Knuschke, P., et al. UVB-induced conversion of 7-dehydrocholesterol to 1α,25-dihydroxyvitamin D3 in an in vitro human skin equivalent model. J. Invest. Dermatol. 117(5), 1179-1185 (2001).

    4. Chen, T.C., Chimeh, F., Lu, Z., et al. Factors that influence the cutaneous synthesis and dietary sources of vitamin D. Arch. Biochem. Biophys. 460(2), 213-217 (2007).