Cis-Trans Isomeric Carotenoids, Vitamins A and Arylpolyenes

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.

Contenu

First Part: Isoprenic Polyenes.

I. Carotenoids: Introduction

Nomenclature

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

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

cis Isomerization in the Visible Region

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

6. Thermal Methods of cis-trans Isomerization

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

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

9. cis-trans Isomerization by Acid Catalysis

10. cis-trans Isomerization by Contact with Active Surfaces

11. cis-trans Isomerization via Boron Trifluoride Complexes

12. Bio-Stereoisomerization

    VI. Preparation of cis Carotenoids by Total Synthesis

    VII. Naturally Occurring cis and Folycis Carotenoids

13. Mono- and Dicis Carotenoids

14. Polycis Carotenoids

    VIII. Some General Remarks on Configurational Assignments

15. Stereoisomeric Types

16. Number and Location of cis Double Bonds

17. Configuration and Infrared Spectrum

    IX. Configurational Assignments in Certain Stereoisomeric Sets

18. Stereoisomeric Sets with Two Hydroaromatic Terminal Groups

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

20. Stereoisomeric Sets with Two Aliphatic Terminal Groups

21. 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

22. Structural Relationships

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

24. Cis-trans Isomerism and Spectra

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

26. Preparation of cis Isomers by Total Synthesis

27. Naturally Occurring cis Vitamins A and Retinenes

28. Chromatographic Separation of Stereoisomers

29. Some Methods used in Configurational Assignments

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

31. Some Stereochemical Aspects of Visual Processes

Second Part: Unbranched Arylpolyenes.

Introductory Remarks

XIII. I-Monoaryl-Polyenes

I-Phenylbutadiene Set

I-Phenylundecapentaenal-(II) Set

XIV. a, -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