Cis-Trans Isomeric Carotenoids, Vitamins A and Arylpolyenes

Cis-Trans Isomeric Carotenoids, Vitamins A and Arylpolyenes

1st Edition - January 1, 1962

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  • Author: L. Zechmeister
  • eBook ISBN: 9781483264936

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Cis-Trans Isomeric Carotenoids, Vitamins A, and Arylpolyenes focuses on the reactions, characteristics, and properties of cis-trans isomeric carotenoids, vitamins A, and arylpolyenes. The publication first takes a look at carotenoids, number, types, and properties of cis carotenoids, and cis-trans isomerism and UV spectra. Discussions focus on simple theoretical interpretation of spectral phenomena, spectra at extremely low temperatures, relative stabilities, melting points, rotatory power, and historical remarks on the stereoisomerism of polyenes. The text then ponders on the preparation of cis carotenoids by direct rearrangement of the all-trans form and total synthesis and naturally occurring cis and polycis carotenoids. The manuscript examines some general remarks on configurational assignments, configurational assignments in certain stereoisomeric sets, and lower-molecular weight carotenoid-carboxylic acids. Topics include bixin set, stereoisomeric sets with two aromatic terminal groups, stereoisomeric sets with one hydroaromatic and one aliphatic terminal group, configuration and infrared spectrum, and stereoisomeric types. The manuscript also elaborates on vitamins A and retinenes, cumulenes with aromatic terminal groups, and polyene azines. The publication is a dependable source of information for researchers interested in cis-trans isomeric carotenoids, vitamins A, and arylpolyenes.

Table of Contents

  • First Part: Isoprenic Polyenes.

    I. Carotenoids: Introduction


    Some Historical Remarks on the Stereoisomerism of Polyenes

    II. Number and Types of cis Carotenoids. Steric Hindrance

    III. Some Properties of cis Carotenoids

    1. Relative Stabilities

    2. Melting Points

    3. Rotatory Power

    4. Relative Adsorption Affinities

    IV. Cis-trans Isomerism and UV Spectra

    1. Some Remarks on the Spectra of all-Trans Carotenoids

    2. Spectral Effect of trans—> cis Isomerization in the Visible Region

    3. Spectral Effect of trans—> cis Isomerization in the Near Ultraviolet Region: The cis-Peak

    4. A Simple Theoretical Interpretation of Spectral Phenomena, Especially of the cis-Peak Effect

    5. Spectra at Extremely Low Temperatures

    V. Preparation of cis Carotenoids by Direct Rearrangement of the All-trans Form

    1. Thermal Methods of cis-trans Isomerization

    2. Photochemical cis-trans Isomerization in the Absence of Catalysts

    3. cis-trans Isomerization by Iodine Catalysis, in Light

    4. cis-trans Isomerization by Acid Catalysis

    5. cis-trans Isomerization by Contact with Active Surfaces

    6. cis-trans Isomerization via Boron Trifluoride Complexes

    7. Bio-Stereoisomerization

    VI. Preparation of cis Carotenoids by Total Synthesis

    VII. Naturally Occurring cis and Folycis Carotenoids

    1. Mono- and Dicis Carotenoids

    2. Polycis Carotenoids

    VIII. Some General Remarks on Configurational Assignments

    1. Stereoisomeric Types

    2. Number and Location of cis Double Bonds

    3. Configuration and Infrared Spectrum

    IX. Configurational Assignments in Certain Stereoisomeric Sets

    1. Stereoisomeric Sets with Two Hydroaromatic Terminal Groups

    2. Stereoisomeric Sets with One Hydroaromatic and One Aliphatic Terminal Group

    3. Stereoisomeric Sets with Two Aliphatic Terminal Groups

    4. Stereoisomeric Sets with Two Aromatic Terminal Groups

    X. Lower-Molecular Weight Carotenoid-carboxylic Acids: Bixin and Crocetin

    Bixin Set

    Crocetin Set

    XI. Cis-trans Isomerism and Provitamin A Effect of Carotenoids

    XII. Vitamins A and Retinenes

    1. Structural Relationships

    2. Number and Character of cis Vitamins A and cis Retinenes

    3. Cis-trans Isomerism and Spectra

    4. Preparation of cis Vitamins A and cis Retinenes by Direct Rearrangement

    5. Preparation of cis Isomers by Total Synthesis

    6. Naturally Occurring cis Vitamins A and Retinenes

    7. Chromatographic Separation of Stereoisomers

    8. Some Methods used in Configurational Assignments

    9. Systemic Bioeffects of cis-trans Isomeric Vitamins A and Retinenes

    10. Some Stereochemical Aspects of Visual Processes

    Second Part: Unbranched Arylpolyenes.

    Introductory Remarks

    XIII. I-Monoaryl-Polyenes

    I-Phenylbutadiene Set

    I-Phenylundecapentaenal-(II) Set

    XIV. α,ω-Diplienylpolyenes and Related Compounds

    1. General Remarks

    2. Stilbene Set

    3. Diphenylbutadiene Set

    4. Diphenylhexatriene Set

    5. Diphenyloctatetraene Set

    6. Sets Containing Bulky End Groups and a Short Conjugated System

    XV. Cumulenes with Aromatic Terminal Groups

    Bis-[2-Nitrodiphenylene]-Butatriene Set

    1,4-Bis-[m-Nitrophenyl]-1,4-Diphenyl-Butatriene Set

    XVI. Polyene Azines

    Cinnamalazine Set

    Phenylpentadienalazine Set

    XVII. Bibliography

    Index of Authors

    Index of Subjects

Product details

  • No. of pages: 266
  • Language: English
  • Copyright: © Academic Press 1962
  • Published: January 1, 1962
  • Imprint: Academic Press
  • eBook ISBN: 9781483264936

About the Author

L. Zechmeister

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