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Steroid


DATA No : SST0006 INFORMANT : Hideaki Nishino

NAME : 5b-Cholestan-3b-ol

COMMON NAME: Coprostenol / 3b-Cholestanol / Stercorin
SYMBOL:
FORMULA: C27H48O1 MOL.WT (average) : 388.669


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:101degC (methanol) (Ref. 0035)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]18/D=+28deg (c=1.8 in chloroform) (Ref. 0036)

DENSITY:

SOLUBILITY:Sol in ethylether, chloroform, benzene. Slightly sol in methanol (1g/145 ml). Sol in water. (Ref. 0036)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA
Separation from cholesterol using TLC. (Ref. 0034)
SOURCE
Feces from human (Ref. 0032/0034) , rat (Ref. 0033) , and carnivorous animals. (Ref. 0036)
CHEMICAL SYNTHESIS
Synthesis by reduction of cholest-5-en-3-one with lithium aluminium hydride. (Ref. 0035/0037) Synthesis by catalytic hydrogenation of coprostenol. (Ref. 0002/0038/0039/0040)
METABOLISM

GENETIC INFORMATION

NOTE
Approximately 360 mg/day in human feces. (Ref. 0032/0034) Positive in Liebermann-Burchard reaction. (Ref. 0032/0033/0034) Reduction by more than one bacterial species. (Ref. 0041)
REFERENCES
[0002]
AUTHOR:Schoenheimer,R., and Evans,Jr.,E.A.
TITLE:Allocholesterol and Epiallocholesterol
JOURNAL:J.Biol.Chem.
VOL:114 PAGE : 567 -582 (1936)
[TOP]

[0032]
AUTHOR:Bondzynski,S.T., and Humnicki,V.
TITLE:Ueber das Schicksal des Cholesterins im Thierischen Organismus
JOURNAL:Z.Physiol.Chem.
VOL:22 PAGE : 396 -410 (1896)
[TOP]

[0033]
AUTHOR:Wells, W. W., Coleman, D. L., and Baumann, C. A.
TITLE:Intestinal sterols. I. Delta7-cholestenol and 7-dehydrocholesterol in feces PubMed ID:13259659
JOURNAL:Arch Biochem Biophys.
VOL:57 PAGE : 437-444 (1955)
[TOP]

[0034]
AUTHOR:Samuel,P., Urivetzky,M., and Kaley,G.
TITLE:Separation and Radioassay of Fecal Cholesterol and Coprosterol Using Thin-Layer Chromatography.
JOURNAL:J.Chromatog.
VOL:14 PAGE : 508 -509 (1964)
[TOP]

[0035]
AUTHOR:Ruzicka,L., Brüngger,H., Eichenberger,E., and Meyer,J.
TITLE:Polyterpene und Polyterpenoide XCI. Zur Präparativen Hersterins und Epi-Dihydro-Cholesterins. Beitrag zur Kenntnis der Räumlichen Lage der Hydroxylgruppe bei den Sterinen.
JOURNAL:Helv.Chim.Acta.
VOL:17 PAGE : 1407 -1416 (1934)
[TOP]

[0036]
AUTHOR:Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp394-394, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0037]
AUTHOR:Shoppee,C.W., and Summers,H.R.
TITLE:Steroids and the Walden Inversion. Part VI. Reduction of Cholest-5-en-3-one with Lithium Alminum Hydride
JOURNAL:J.Chem.Soc.
VOL:1950 PAGE : 687 -689 (1950)
[TOP]

[0038]
AUTHOR:Ruzicka,L., Furter,M., and Goldberg,M.W.
TITLE:Über Steroide und Sexualhormone (42. Mitteilung) Zur Stereo Chemie Epimerer Steroider Alkohole Mit Einem Hydroxyl in den Stellungen 3 Odor 17.
JOURNAL:Helv.Chim.Acta
VOL:21 PAGE : 498 -514 (1938)
[TOP]

[0039]
AUTHOR:Shoppee,C.W., Agashe, B.D., and Summers,G.H.R.
TITLE:Steroids. Part XIII. Catalytic Hydrogenation of 3a- and 3b-Substituted D4-Steroids.
JOURNAL:J.Chem.Soc.
VOL:1957 PAGE : 3107 -3112 (1957)
[TOP]

[0040]
AUTHOR:Dart,M.C., and Henbest,H.B.
TITLE:Aspects of Stereochemistry. Part XV. Catalytic Hydrogenation of Cyclic Allylic Alcohols in the Presence of Sodium Nitrite.
JOURNAL:J.Chem.Soc.
VOL:1960 PAGE : 3563 -3570 (1960)
[TOP]

[0041]
AUTHOR:Rosenfeld,R.S., and Gallagher,T.F.
TITLE:Further Studies of the Biotransformation of Cholesterol to Coprostanol.
JOURNAL:Steroids
VOL:4 PAGE : 515 -520 (1964)
[TOP]

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