Crystal structure of cholic acid with no guest molecules

Miki, Kunio; Kasai, Nobutami; Shibakami, Motonari; Chirachanchai, Suwabun; Takemoto, Kiichi; Miyata, Mikiji

doi:10.1107/s0108270190005224

Cited by 28 publications

(16 citation statements)

References 5 publications

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“…In addition, the peak at 1716 cm Ϫ1 also disappeared and a new diffraction peaks was observed at 1722 cm Ϫ1 . Miki et al 25) reported that CA crystals (with no guest molecules) showed no channel structure whereas CA-guest complexes demonstrated the bilayer channel structure where guest molecules were accommodated. 7) The channel structure was formed by the hydrogen bonds, which were not observed in CA crystals, between CϭO and OH groups of adjacent CA molecules.…”

Section: Resultsmentioning

confidence: 99%

Elucidation of Solid-State Complexation in Ground Mixtures of Cholic Acid and Guest Compounds.

Oguchi

Tozuka

Hanawa

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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The solid-state complexation between cholic acid (CA) and either methyl p-hydroxybenzoate (MPB) or ibuprofen (IBP) was investigated. Powder X-ray diffractometry, IR spectroscopy and thermal analysis suggested the complex formation between CA and MPB as well as between CA and IBP by co-grinding method. The stoichiometry of CA-MPB was 1 : 1 while that of CA-IBP was 2 : 1, reflecting the effect of guest size on complex formation. The guest compounds were assumed to be included in the channel of complexes formed by hydrogen bonds among CA molecules.

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Section: Resultsmentioning

confidence: 99%

Elucidation of Solid-State Complexation in Ground Mixtures of Cholic Acid and Guest Compounds.

Oguchi

Tozuka

Hanawa

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The inclination of the molecules with respect to the 2 1 axis that at first glance is observed in Figure 7a suggests that the degree of molecular tilt in 1 is intermediate to those ones. To evaluate the molecular tilt in the case of cholic acid, we have used the only available cif corresponding to its crystalline structure free of guests (solvents) [51], and a value of 41.5 • was obtained. Although deoxycholic acid has been recrystallized in a large number of solvents, unfortunately, any crystal structure free of solvent molecules has been reported.…”

Section: Helical Assembliesmentioning

confidence: 99%

Crystal Structure of a Cationic Bile Salt Derivative ([3β,5β,7α,12α]-3-(2-naphthyloylamino)-7,12-dihydroxycholan-24-triethylammonium iodide)

et al. 2019

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The crystal structure of the iodide salt of a quaternary ammonium derivative of cholic acid having a naphthalene group attached to the 3rd position of the steroid nucleus through an amide bond ([3,5,7,12]-3-(2-naphthyloylamino)-7,12-dihydroxycholan-24-triethylammonium iodide) has been resolved. The compound crystallizes in the P212121 orthorhombic space group (a/Å = 10.9458(3); b/Å = 12.1625(3); c/Å = 28.4706(7)). The lateral chain adopts a fully extended tttt conformation because the quaternary ammonium group cannot participate in the formation of hydrogen bonds. The iodide ion is involved in the formation of hydrogen bonds as well as the amide group and the two steroid hydroxy groups. Hirshfeld surface analysis confirms that these contacts, as well as the electrostatic interactions, stabilize the structure. The helixes around the 21 screw axis are right-handed ones.

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“…Infinite chain of cooperative Á Á ÁO-HÁ Á ÁOÁ Á Á hydrogen bonds in crystals of CA with no guest molecules. Molecular aggregation in corrugated layers in the structure of CA with no guest molecules (Miki et al, 1990). Criterion for observed reflections…”

Section: Figurementioning

confidence: 99%

“…The crystal structure of cholic acid with no guest molecules (Miki et al, 1990) displays a supramolecular architecture where the molecules form corrugated layers held together by hydrophilic and lipophilic interactions (Fig. 3).…”

Section: Introductionmentioning

confidence: 99%

Hydrogen-bonded aggregations of oxo-cholic acids

Bertolasi¹,

Ferretti²,

Pretto³

et al. 2005

Acta Crystallogr Sect B

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The crystal structures of six new crystals of oxo-cholic acids (oxo-CA) are reported: (I) 3alpha,12alpha-dihydroxy-7-oxo-5beta-cholan-24-oic acid; (II) 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid; (III) 7alpha-hydroxy-3,12-dioxo-5beta-cholan-24-oic acid; (IV-alpha) and (IV-beta) 12alpha-hydroxy-3,7-dioxo-5beta-cholan-24-oic acid; (V) 3,7,12-trihydroxy-5beta-cholan-24-oic acid. (IV-beta) is a pseudopolymorphic solvated form of (IV-alpha) and contains small channels which can trap disordered water molecules. In all the structures the four saturated cycles, forming the common alicyclic skeleton, have the same conformation, while the carboxylic side chain adopts flexible conformations in order to produce the most efficient crystal aggregations. The structures display a variety of supramolecular architectures dominated by networks of cooperative O-H...O hydrogen bonds forming different packing motifs often supported by weaker C-H...O interactions.

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Crystal structure of cholic acid with no guest molecules

Cited by 28 publications

References 5 publications

Elucidation of Solid-State Complexation in Ground Mixtures of Cholic Acid and Guest Compounds.

Elucidation of Solid-State Complexation in Ground Mixtures of Cholic Acid and Guest Compounds.

Crystal Structure of a Cationic Bile Salt Derivative ([3β,5β,7α,12α]-3-(2-naphthyloylamino)-7,12-dihydroxycholan-24-triethylammonium iodide)

Hydrogen-bonded aggregations of oxo-cholic acids

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