X-ray structural investigation of gossypol and its derivatives. XXVIII. Separation of the dilactol tautomeric form of gossypol hexamethyl ether into individual stereoisomers and evaluation of their clathrate-forming capacity

Ибрагимов, Б. Т.; Beketov, K. M.; Talipov, S. A.; Mardanov, R. G.

doi:10.1007/bf01164883

Cited by 4 publications

(2 citation statements)

References 3 publications

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“…The gossypol molecules within this complex are in the aldehyde form. This feature is exhibited by all gossypol-con-taining crystal structures reported to date, but is not exhibited for gossypol derivatives (14,16). Both naphthalene moieties of the structure are close to planar with root-mean-squared atomic deviations from least-squares best-fit planes of 0.047 and 0.032 Å.…”

Section: Resultsmentioning

confidence: 81%

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Crystal and molecular structure of an enantiomeric gossypol‐acetic acid clathrate

Dowd

Thomas

Calhoun

1999

J Americ Oil Chem Soc

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Single crystals of gossypol with three molecules of acetic acid (gossypol triacetic acid) were grown from solutions of gossypol acetic acid and acetone. The crystals were unstable in air but could be stabilized for X-ray diffraction analysis by coating the crystal surfaces with a thin layer of mineral oil. The gossypol triacetic acid complex (C 30 H 30 O 8 ·3C 2 H 4 O 2 ) forms an orthorhombic crystal system with P2 1 2 1 2 1 (Z = 4) symmetry. Unit cell dimensions were a = 9.0208(7) Å, b = 17.4884(10) Å, and c = 24.358(2), Å yielding a volume of 3842.7(5) Å 3 and a density of 1.2077(2) g/cm 3 . As with all previously reported crystals of gossypol, the gossypol molecules were of the aldehyde tautomer, and the two planar naphthalene rings were approximately perpendicular. Acetic acid molecules were found to lie in channels within the gossypol matrix. Individual crystals contained only one gossypol enantiomer, but both enantiomers crystallized from solution. Although the crystal habit could not be used to distinguish between the gossypol enantiomers, a fragment of the crystal could be derivatized and analyzed by high-performance liquid chromatography for this purpose. The ability to grow large, nonracemic crystals leads to a simple procedure for separating small quantities of the individual gossypol enantiomers.

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Section: Resultsmentioning

confidence: 81%

“…The best-studied example is the clathrate formed with dichloromethane, which forms both monoclinic and triclinic crystals with host/guest ratios of 1:1 as well as a triclinic crystal with a host/guest ratio of 1:2 (13). Crystal structures have also been reported for several gossypol derivatives (14)(15)(16).…”

mentioning

confidence: 95%

Crystal and molecular structure of an enantiomeric gossypol‐acetic acid clathrate

Dowd

Thomas

Calhoun

1999

J Americ Oil Chem Soc

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Chapter 6 Gossypol-A Polyphenolic Compound from Cotton Plant

Wang

Howell

Chen

et al. 2009

Advances in Food and Nutrition Research

114

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Molecular and crystal structure of gossypol tetramethyl ether with an unknown solvate

Honkeldieva¹,

Talipov²,

Mardanov³

et al. 2015

Acta Cryst E

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The title compound consists of two planar halves. There is one half-molecule in the asymmetric unit, the whole molecule being generated by twofold rotation symmetry. The crystal structure has wide channels of 5–6 Å in diameter extending along the c-axis direction. The molecules are associated into a three-dimensional network supported by some weak C—H⋯O hydrogen bonds and C—H⋯π interactions.

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X-ray structural investigation of gossypol and its derivatives. XXVIII. Separation of the dilactol tautomeric form of gossypol hexamethyl ether into individual stereoisomers and evaluation of their clathrate-forming capacity

Cited by 4 publications

References 3 publications

Crystal and molecular structure of an enantiomeric gossypol‐acetic acid clathrate

Crystal and molecular structure of an enantiomeric gossypol‐acetic acid clathrate

Chapter 6 Gossypol-A Polyphenolic Compound from Cotton Plant

Molecular and crystal structure of gossypol tetramethyl ether with an unknown solvate

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