Structural, Thermoanalytical and Molecular Modeling Studies on N-(3-hydroxypropyl) 3α,12α-Dihydroxy-5β-cholan-24-amide and Its Monohydrates

doi:10.3390/12092161

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Molecules 2007, 12(9), 2161-2178; doi:10.3390/12092161

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Structural, Thermoanalytical and Molecular Modeling Studies on N-(3-hydroxypropyl) 3α,12α-Dihydroxy-5β-cholan-24-amide and Its Monohydrates

Arto Valkonen* , Erkki Kolehmainen, Manu Lahtinen, Elina Sievänen, Virpi Noponen, Minna Tolonen and Reijo Kauppinen

Department of Chemistry, University of Jyväskylä, PO. Box 35, FIN-40014 University of Jyväskylä, Finland

* Author to whom correspondence should be addressed.

Received: 17 August 2007; in revised form: 9 September 2007 / Accepted: 12 September 2007 / Published: 12 September 2007

(This article belongs to the Special Issue Bile Acids)

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Abstract: The synthetic method for preparing N-(3-hydroxypropyl) 3α,12α-dihydroxy-5β- cholan-24-amide can lead to formation of at least three different crystal forms – an anhydrous compound and two monohydrates. The structural and thermal properties of these forms have been characterized by 13C-CP/MAS-NMR and IR spectroscopy, thermo- gravimetry, differential scanning calorimetry and by powder and single crystal x-ray crystallography. In addition, theoretical 13C-NMR chemical shift calculations were also performed for the anhydrous compound and for the first monohydrate, starting from single crystal structures and the structures of these species have now been verified. The first monohydrate, C27H47NO4 · H2O, crystallizes in orthorhombic space group P212121 with cell parameters: a = 7.1148(2), b = 18.1775(5), c = 20.1813(6), Z = 4.

Keywords: Bile acids; 13C-CP/MAS-NMR spectroscopy; crystallography; thermal Bile acids; 13C-CP/MAS-NMR spectroscopy; crystallography; thermal analysis; solid state structure.

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MDPI and ACS Style

Valkonen, A.; Kolehmainen, E.; Lahtinen, M.; Sievänen, E.; Noponen, V.; Tolonen, M.; Kauppinen, R. Structural, Thermoanalytical and Molecular Modeling Studies on N-(3-hydroxypropyl) 3α,12α-Dihydroxy-5β-cholan-24-amide and Its Monohydrates. Molecules 2007, 12, 2161-2178.

AMA Style

Valkonen A, Kolehmainen E, Lahtinen M, Sievänen E, Noponen V, Tolonen M, Kauppinen R. Structural, Thermoanalytical and Molecular Modeling Studies on N-(3-hydroxypropyl) 3α,12α-Dihydroxy-5β-cholan-24-amide and Its Monohydrates. Molecules. 2007; 12(9):2161-2178.

Chicago/Turabian Style

Valkonen, Arto; Kolehmainen, Erkki; Lahtinen, Manu; Sievänen, Elina; Noponen, Virpi; Tolonen, Minna; Kauppinen, Reijo. 2007. "Structural, Thermoanalytical and Molecular Modeling Studies on N-(3-hydroxypropyl) 3α,12α-Dihydroxy-5β-cholan-24-amide and Its Monohydrates." Molecules 12, no. 9: 2161-2178.

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