Naturally Occurring cis and Polycis Carotenoids
As we have seen, the overwhelming majority of plant carotenoids possess the all-trans configuration. To what extent the more energy-rich cis carotenoids appear in plants and animals is a question of biological and genetical interest. The relative scarcity
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L. ZBCHMBISTBR CALIFORNIA INSTITUTE OF TECHNOLOGY PASADENA, CALIFORNIA
WITH 112 FIGURES
1962 NEW YORK
ACADEMIC PRESS INC. PUBLISHERS VIENNA
SPRINGER",VERLAG
SPRINGER-VERLAG VIENNA
Published in USA and Canada by ACADEMIC PRESS INC., PUBLISHERS I I I Filth Avenue, New York 3, New York
ISBN-13: 978-3-7091-5550-9 e-ISBN-13: 978-3-7091-5548-6 DOl: 10.1007/978-3-7091-5548-6
Lib,ary of Congress Catalog Card Number 62-14142 All rights reserved No part 01 this book may be reproduced in any form, by miaolilm or any other _ans. without permission in writing from the publishers
© BY SPRINGER-VERLAG VIENNA 1902 SOF'l'COVER REPRINT OF THE HARDCOVER 1ST EDmON
1902
TO ELIZABETH
Preface. The core of this little book is a survey of the experimental work carried out by our research group in the course of two decades. Although the writer has made an effort to present and evaluate related contributions of many authors, the text should not be considered as a monograph of encyclopedic character. Our experiments began with a study of cis-Irans-isomeric C40carotenoids and were subsequently extended to other types of polyenes in order to determine how far the observations were applicable to broader fields. Similar considerations have led to the inclusion of the Chapters on Vitamins A and on Cumulenes although we have not contributed to the stereochemistry of these classes of compounds. The first eleven Chapters have been published in Volume XVIII of the Series, "Progress in the Chemistry of Organic Natural Products" and now appear in a revised, up-to-date form. Sincere thanks are due to the following former members of our research group who have participated in the experimental elucidition of the field: W. V. Bush, A. Chatterjee, L. Cholnoky, J. Dale, R. B. Escue, P. Fischer Jorgensen, Ch. Gansser, F. T. Haxo, G. Karmakar, B. K. Koe, J. Leemann, R. M. Lemmon, the late A. L. LeRosen, W. Lijinsky, K. Lunde, E. F. Magoon, W. H. McNeely, F. J. Petracek, J. H. Pinckard, A. Polgar, A. Sandoval, W. A. Schroeder, J. W. Sease, Y. W. Tang, K. Tsukida, the late P. Tuzson, L. Wallcave, and B. Wille. Dr. Bush has kindly read the manuscript and the galleys. . The reader will note that much of the material presented on the following pages is of empirical nature. It is hoped, however, that younger investigators who have newer and more refined experimental tools at their disposal will develop theoretical explanations for' many of the recorded phenomena, physical, chemical and biological. Pasadena, Autumn 1961.
L. Z.
Contents. First Part: Isoprenic Polyenes.
Page
1. Carotenoids: Introduction ....................................... .
3
Nomenclature ................................................. . Some Historical Remarks on the Stereoisomerism of Polyenes ..... .
7
II. Number and Types of cis Carotenoids. Steric Hindrance ....... " ..
II
III. Some Properties of cis Carotenoids .............................. . I. Relative Stabilities .......................................... . Sterically Unhindered cis Forms .......................
