Cholestanol

Coprostanol

Names
IUPAC name 5β-cholestan-3β-ol
Other names 5β-coprostanol coprostanol
Identifiers
CAS Number	360-68-9 Y
3D model (JSmol)	Interactive image
ChemSpider	191826 N
ECHA InfoCard	100.006.036
PubChem CID	221122
InChI InChI=1S/C27H48O/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/h18-25,28H,6-17H2,1-5H3/t19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1 N Key: QYIXCDOBOSTCEI-NWKZBHTNSA-N N InChI=1/C27H48O/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/h18-25,28H,6-17H2,1-5H3/t19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1 Key: QYIXCDOBOSTCEI-NWKZBHTNBU
SMILES O[C@H]4CC[C@]3([C@H](CC[C@H]2[C@@H]1CC[C@@H]([C@@]1(C)CC[C@@H]23)[C@H](C)CCCC(C)C)C4)C
Properties
Chemical formula	C27H48O
Molar mass	388.6756 g/mol
Melting point	102 °C (216 °F; 375 K)
Hazards
Flash point	Non-flammable
Related compounds
Related Stanols	24-ethyl coprostanol 5α-cholestanol epi-coprostanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

5β-Coprostanol (5β-cholestan-3β-ol) is a 27-carbon stanol formed from the biohydrogenation of cholesterol (cholest-5en-3β-ol) in the gut of most higher animals and birds. This compound has frequently been used as a biomarker for the presence of human faecal matter in the environment.

5β-coprostanol has a low water solubility, and consequently a high octanol – water partition coefficient (log Kow = 8.82). This means that in most environmental systems, 5β-coprostanol will be associated with the solid phase.

In anaerobic sediments and soils, 5β-coprostanol is stable for many hundreds of years enabling it to be used as an indicator of past faecal discharges. As such, records of 5β-coprostanol from paleo-environmental archives have been used to further constrain the timing of human settlements in a region, as well as reconstruct relative changes in human populations and agricultural activities over several thousand years.

Since the molecule has a hydroxyl (-OH) group, it is frequently bound to other lipids including fatty acids; most analytical methods, therefore, utilise a strong alkali (KOH or NaOH) to saponify the ester linkages. Typical extraction solvents include 6% KOH in methanol. The free sterols and stanols (saturated sterols) are then separated from the polar lipids by partitioning into a less polar solvent (e.g. hexane). Prior to analysis, the hydroxyl group is frequently derivatised with BSTFA (bis-trimethyl silyl trifluoroacetamide) to replace the hydrogen with the less exchangeable trimethylsilyl (TMS) group. Instrumental analysis is frequently conducted on gas chromatograph (GC) with either a flame ionisation detector (FID) or mass spectrometer (MS). The mass spectrum for 5β-coprostanol - TMS ether can be seen in the figure.