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CHEMISTRY OF HOP CONSTITUENTS: XXII. PROTON MAGNETIC RESONANCE SPECTROSCOPY OF ISO HUMULONE A
Author(s) -
Burton J. S.,
Stevens R.,
Elvidge J. A.
Publication year - 1964
Publication title -
journal of the institute of brewing
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.523
H-Index - 51
eISSN - 2050-0416
pISSN - 0046-9750
DOI - 10.1002/j.2050-0416.1964.tb02002.x
Subject(s) - chemistry , deuterium , proton magnetic resonance , hydrolysis , proton , nuclear magnetic resonance spectroscopy , spectral line , cis–trans isomerism , spectroscopy , oxide , hop (telecommunications) , stereochemistry , nuclear magnetic resonance , organic chemistry , physics , quantum mechanics , computer network , astronomy , computer science
Knowledge of the structure of iso humulone A is reviewed. Its proton magnetic resonance spectrum has been interpreted with the aid of the spectra of the two isomers of humulinic acid. It is concluded that iso humulone A consists of a mixture of stereoisomers, trans and cis with respect to the 4‐ iso hexenoyl and 5‐ iso pentenyl chains, in the ratio of about 60% trans ( i.e ., with the stereochemistry of humulinic acid B) to 40% cis ( i.e ., humulinic acid A stereochemistry). Humulone has been isomerized into iso humulone A in deuterium oxide, and unlabelled iso humulone A has been hydrolysed into humulinic acid A using sodium deuteroxide in deuterium oxide. The modified spectra assisted some of the assignments.