Determination of molecular associations of some hydrophobic and hydrophilic bile acids by infrared and Raman spectroscopy.
The aim of this study was to analyse the Raman and infrared spectra of eight common mammalian bile acids in order to identify intermolecular interactions between hydroxyl and carbonyl groups. The results are considered in the light of the new hydrophilic/hydrophobic classification of bile acids. The alcohol OH group of the hydrophobic bile acids forms different intermolecular bonds. The most hydrophobic bile acid, lithocholic acid forms polymers, and this may explain its very low water solubility. The hydrophilic bile acids have some of their alcohol OH groups free of any intermolecular interaction. The strongly hydrophilic murideoxycholic acid also forms dimers, again consistent with a very low water solubility. The proposed structural arrangements are in agreement with published crystallographic studies.
Lamcharfi
E
E
Département de Chimie, Université Sidi Mohammed ben Abdellah, Faculté des Sciences et Techniques Fès-Saiss, Fès, Maroc.
Cohen-Solal
C
C
Parquet
M
M
Lutton
C
C
Dupré
J
J
Meyer
C
C
D000818:Animals; D001647:Bile Acids and Salts / Q000737:chemistry*; D002635:Chenodeoxycholic Acid / Q000737:chemistry; D019826:Cholic Acid; D002793:Cholic Acids / Q000737:chemistry; D003840:Deoxycholic Acid / Q000737:chemistry; D008095:Lithocholic Acid / Q000737:chemistry; D008322:Mammals; D008958:Models, Molecular; D008968:Molecular Conformation; D012997:Solvents; D013055:Spectrophotometry, Infrared; D013059:Spectrum Analysis, Raman; D013329:Structure-Activity Relationship; D014580:Ursodeoxycholic Acid / Q000737:chemistry
D001647:Bile Acids and Salts; D002793:Cholic Acids; D012997:Solvents; D003840:Deoxycholic Acid; D002635:Chenodeoxycholic Acid; C004821:muricholic acid; D008095:Lithocholic Acid; D014580:Ursodeoxycholic Acid; C010471:hyodeoxycholic acid; D019826:Cholic Acid