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CHEMICAL STRUCTURES OF HUMULONE AND LUPULONE: A BRIEF REVIEW
Author(s) -
Harris G.,
Howard G. A.,
Pollock J. R. A.
Publication year - 1952
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.2050-0416.1952.tb06191.x
Subject(s) - hydrogenolysis , chemistry , isopentane , carbon fibers , organic chemistry , materials science , catalysis , composite number , composite material
Attention is drawn to the fact that the Wllmer‐Wieland formulations for humulone and lupulone are inconsistent with the behaviour of these substances on hydrogenolysis, since the observed liberation of iso pentane would involve the rupture of a carbon‐carbon bond; no other example of hydrogenolysis effecting such rupture is known. The difficulty is overcome if the presence of a carbon‐oxygen bond of the dimethylallyl ether type is assumed. A benzenoid structure may be assumed for lupulone but not for humulone. Evidence is adduced in support of formulae which admit these facts, and it is claimed that these formulae are not inconsistent with recent syntheses.