Journal of Chemical Crystallography p. 697 - 702 (2011)
Update date:2022-08-04
Topics:
Balu, Devipriya
Poomani, Kumaradhas
Nagabushanam, Kalyanam
Balasubramanium, Sridhar
Ramanujam, Rajendran
Muhammed, Majeed
5-Lipoxygenase inhibitor 3-O-acetyl-9,11-dehydro-β-boswellic acid was detected in the extract of Boswellia serrata gum resulting from unstable 11-hydroxy precursor. It was reported more potent than other Boswellic acids in its inhibition of 5-Lipoxygenase. Here, we report the method of conversion of 3-acetoxy-β-boswellic acid to 3-O-acetyl-9,11-dehydro-β-boswellic acid, and the crystal structure of later. This compound crystallizes in orthorhombic space group P212121 with cell parameters of a = 12.726(1) A, b = 16.597(1) A, c = 27.332(2) A, α = β = γ = 90°, V = 5772.7(5) A3, D c = 1.143 Mg/m3, and Z = 8. The X-ray structure investigation indicates that the rings A, B, D and E are exhibit chair and the ring C adopts a distorted half chair conformation. The conformational difference of the two structures in the arrangement is due to crystal packing of 3-O-acetyl-9,11-dehydro-β-boswellic acid. The molecular packing is stabilized by C-H...O and O-H...O types of hydrogen bonding interactions. Graphical Abstract: Synthesis and crystal structure analysis of 5-Lipoxygenase Inhibitor 3-O-acetyl-9,11-dehydro-β-boswellic acid are reported. Rings A, B, D and E of the inhibitor adopt chair conformation and the C-ring exhibit a distorted half chair conformation. The molecular packing is stabilized by C-H...O and O-H...O types of hydrogen bonding interactions.
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