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24-dehydro Cholesterol

Item № 14943
CAS № 313-04-2
Purity ≥98%
product image
                (CAS 313-04-2)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $25.00 0.00
     5 mg $50.00 0.00
     10 mg $88.00 0.00
     25 mg $188.00 0.00

Pricing updated 2019-07-17. Prices are subject to change without notice.

Description
Synonyms
  • Desmosterol
  • NSC 226126

24-dehydro Cholesterol is an immediate precursor to cholesterol in the Bloch pathway of cholesterol biosynthesis. Structurally, it varies from cholesterol only by a single double bond at carbon 24 and has been used as cholesterol substitute in cellular membrane studies.1 During brain development, 24-dehydro cholesterol transiently accumulates, composing up to 30% of total brain sterol, where it is poised to rapidly enrich membrane sterols.2 However, defects in cholesterol synthesis can lead to a condition called, desmosterolosis, which results in an accumulation of excess 24-dehydro cholesterol.3 24-dehydro Cholesterol has been reported to activate liver X receptor-target genes in both the liver of cholesterol-free mice and in cholesterol-starved macrophage foam cells in atherosclerotic lesions.4,5

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Technical Information
Formal Name
(3β)-cholesta-5,24-dien-3-ol
CAS Number
313-04-2
Synonyms
  • Desmosterol
  • NSC 226126
Molecular Formula
C27H44O
Formula Weight
384.6
Purity
≥98%
Formulation
A crystalline solid
SMILES
C/C(C)=C/CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])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/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI Key
AVSXSVCZWQODGV-DPAQBDIFSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Huster, D., Scheidt, H.A., Arnold, K., et al. Desmosterol may replace cholesterol in lipid membranes Biophys. J. 88(3), 1838-1844 (2005).

2. Jansen, M., Wang, W., Greco, D., et al. What dictates the accumulation of desmosterol in the developing brain? FASEB J. 27(3), 865-870 (2013).

3. Clayton, P.T. Disorders of cholesterol biosynthesis Arch. Dis. Child. 78(2), 185-189 (1998).

4. Heverin, M., Meaney, S., Brafman, A., et al. Studies on the cholesterol-free mouse: Strong activation of LXR-regulated hepatic genes when replacing cholesterol with desmosterol Arterioscler. Thromb. Vasc. Biol. 27(10), 2191-2197 (2007).

5. Spann, N.J., Garmire, L.X., McDonald, J.G., et al. Regulated accumulation of desmosterol integrates macrophage lipid metabolism and inflammatory responses Cell 151(1), 138-152 (2012).

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