Atheronals

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Atheronals
Atheronal A
Atheronal B
Names
IUPAC names
A: 3β-Hydroxy-5-oxo-5,6-secocholestan-6-al
B: 3β-Hydroxy-5β-hydroxy-B-norcholestane-6β-carboxaldehyde
Identifiers
3D model (JSmol)
  • A: InChI=1S/C27H46O3/c1-18(2)7-6-8-19(3)22-9-10-23-21(13-16-28)24(12-15-26(22,23)4)27(5)14-11-20(29)17-25(27)30/h16,18-24,29H,6-15,17H2,1-5H3/t19-,20+,21+,22-,23+,24+,26-,27-/m1/s1
    Key: YAKOGNWFSAFQBB-MCFZVKJISA-N
  • B: InChI=1S/C27H46O3/c1-17(2)7-6-8-18(3)20-9-10-21-24-22(12-13-25(20,21)4)26(5)14-11-19(29)15-27(26,30)23(24)16-28/h16-24,29-30H,6-15H2,1-5H3/t18-,19+,20-,21?,22?,23-,24?,25-,26-,27-/m1/s1
    Key: XILGKUFKDWNZBF-PWNNJZATSA-N
  • A: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@@H]([C@H]2CC=O)[C@]3(CC[C@@H](CC3=O)O)C)C
  • B: C[C@H](CCCC(C)C)[C@H]1CCC2[C@@]1(CCC3C2[C@H]([C@]4([C@@]3(CC[C@@H](C4)O)C)O)C=O)C
Properties
C27H46O3
Molar mass 418.662 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Atheronals are biologically relevant oxysterols formed in the reaction of cholesterol with ozone. Atheronal A (secosterol A) is the major product of ozonolysis which is 3β-hydroxy-5-oxo-5,6-secocholestan-6-al. Atheronal B (secosterol B) is formed by the intramolecular aldol reaction of atheronal A, which is 3β-hydroxy-5β-hydroxy-B-norcholestane-6β-carboxaldehyde.

Effects of atheronals in human body

References

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