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24-Ethyl coprostanol

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(Redirected from (3β,5β)-stigmastan-3-ol)
24-Ethyl coprostanol
Names
IUPAC name
5β-Stigmastan-3β-ol
Systematic IUPAC name
(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-1-[(2R)-5-Ethyl-6-methylheptan-2-yl]-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-ol
Other names
(3β,5β)-Stigmastan-3-ol,
(24R)-Ethylcoprostanol,
24a-Ethylcoprostanol,
Copro-β-sitostanol,
Coprostigmastanol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3/t20-,21?,22-,23+,24+,25-,26+,27+,28+,29-/m1/s1
    Key: LGJMUZUPVCAVPU-OKGOGUTDSA-N
  • O[C@H]1CC[C@@]2(C)[C@@](CC[C@]3([H])[C@@]([H])2CC[C@@]4(C)[C@]([H])3CC[C@@]([H])4[C@@H](CCC(CC)C(C)C)C)([H])C1
Properties
C29H52O
Molar mass 416.72
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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24-Ethyl coprostanol (24-ethyl 5β-cholestan-3β-ol) is a 29 carbon stanol formed from the biohydrogenation of β-sitosterol (24-ethyl cholest-5en-3β-ol, 24-ethyl cholesterol) in the gastrointestinal tract of most higher animals, especially herbivores.[1] This compound has been used as a biomarker for the presence of agricultural (non-human) faecal matter in nature.

References

[edit]
  1. ^ "24-Ethyl coprostanol | C29H52O | ChemSpider". www.chemspider.com. Retrieved 2022-11-15.