Chiroptical spectroscopic studies for the absolute configuration determination of hexahydrocurcumin and octahydrocurcumin. Issue 12 (27th October 2022)

• Record Type: Journal Article
• Authors: Puente, Andrew R.; Nagabhushanam, Kalyanam; Ganjihal, Savita; Majeed, Muhammed; Polavarapu, Prasad L.
• Is Part Of: Chirality. Volume 34:Issue 12(2022)
• Page Start: 1515
• Page End: 1525
• Publication Date: 2022-10-27
• Subjects: absolute configuration -- electronic circular dichroism -- hexahydrocurcumin -- octahydrocurcumin -- specific rotation -- vibrational circular dichroism; Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.23511
• Languages: English
• ISSNs: 0899-0042

Abstract

Abstract: Hexahydrocurcumin (HHC) and octahydrocurcumin (OHC) were synthesized, and their enantiomers were separated using supercritical fluid chromatography. The absolute configurations (ACs) of HHC and OHC were independently determined using experimental measurements and quantum theoretical predictions of vibrational circular dichroism, electronic circular dichroism, and optical rotatory dispersion. These studies lead to AC assignments of (−)‐( R )‐HHC and (+)‐( R, R )‐OHC. The AC of OHC is further confirmed by its structure determined from single crystal x‐ray diffraction. Abstract : The racemic hexahydrocurcumin and octahydrocurcumin were synthesized, their individual enantiomers separated using supercritical fluid chromatography and the absolute configurations determined using vibrational circular dichroism, electronic circular dichroism, optical rotatory dispersion, and x‐ray diffraction.