Related Experiment Video
Updated: Jun 1, 2026

Cellular Lipid Extraction for Targeted Stable Isotope Dilution Liquid Chromatography-Mass Spectrometry Analysis
Published on: November 17, 2011
3α-Hydr-oxy-N-(3-hydroxy-prop-yl)-5β-cholan-24-amide
Arto Valkonen1, Juha Koivukorpi, Manu Lahtinen
1University of Jyväskylä, Department of Chemistry, PO Box 35, FIN-40014 Jyväskylä, Finland.
Abstract:
The title compound, C(27)H(47)NO(3), is a (3-hydroxy-prop-yl)amide derivative of naturally occurring enanti-opure lithocholic acid (3α-hydr-oxy-5β-cholan-24-oic acid). The mol-ecule contains four fused rings: three six-membered rings in chair conformations and one five-membered ring in a half-chair form. The two terminal six-membered rings are cis-fused, while other rings are trans-fused. The structure contains an intra-molecular O-H⋯O hydrogen bond and a similar hydrogen-bond framework to the corresponding deoxy-cholic and chenodeoxy-cholic acid derivatives. Inter-molecular O-H⋯O and N-H⋯O inter-actions are also present in the crystal. This compound seems to have at least two polymorphic forms from a comparison of the X-ray powder pattern simulated from the present structure of the title compound and that previously obtained for the powder sample.
Related Concept Videos
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Formation of Halohydrin from Alkenes
Prochirality
Adrenergic Agonists: Chemistry and Structure-Activity Relationship
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
Multiple Halogenation of Methyl Ketones: Haloform Reaction
α-Halogenation of Carboxylic Acid Derivatives: Overview

