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The Journal of General Physiology
Article . 1953 . Peer-reviewed
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GEOMETRICAL ISOMERS OF RETINENE

Authors: R, HUBBARD; R I, GREGERMAN; G, WALD;

GEOMETRICAL ISOMERS OF RETINENE

Abstract

Five crystalline retinenes have been isolated, which have every appearance of being cis-trans isomers of one another. They are all-trans retinene; three apparently mono-cis isomers: neoretinenes a and b and isoretinene a; and isoretinene b, an apparently di-cis isomer. The absorption spectra of these substances display the relations expected of cis-trans isomers. The main absorption band is displaced 5.5 to 7 mµ toward shorter wave lengths for each presumptive cis linkage. Some of the presumptive cis isomers also display a cis peak at 255 to 260 mµ. All five substances yield an identical blue product on mixing with antimony chloride. All of them are converted by light to what appears to be an identical mixture of stereoisomers. Heat isomerizes them very slowly; only neoretinene b exhibits large changes on heating at 70°C. for 3 hours. The various isomers have been extensively interconverted by gentle procedures, and all of them have been converted to all-trans retinene. The present theory of cis-trans isomerism in carotenoids predicts the existence of four stable isomers of retinene. Instead we seem to have five—specifically three mono-cis forms where two are expected. There is no doubt that all these substances are closely related isomers of one another. The only point in question is whether they differ in part by something other than cis-trans configuration. One possibility, as yet little supported by evidence, is that isomerization between ß- and α-ionone rings may be involved. If, however, as seems more likely, all these substances are geometrical isomers of one another, some modification is needed in the present theory of configurational relationships in this class of compounds.

Related Organizations
Keywords

Hot Temperature, Isomerism, Light, Retinaldehyde, Pigments, Biological, Norisoprenoids, Retina

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
79
Top 10%
Top 1%
Top 10%
Published in a Diamond OA journal