Abstract
Following the preparation of rich concentrates of vitamin A (vitamin A alcohol, vitamin A1, axerophthol) from the unsaponifiable matter of fish liver oils, the following formula was established by Karrer, Morf and Schöpp (89):
The work on synthetic vitamin A in this Laboratory has been cooperative in nature and in certain references to unpublished work in the review [Dist. Prod. Ind. (23)] the author acts as spokesman for a group in which J. D. Cawley, C. D. Robeson, L. Weisler and E. M. Shantz have made major contributions and A. J. Chechak, F. B. Clough, C. C. Eddinger, N. D. Embree, G. R. Seideland M. H. Stern have given valuable assistance. The help of the Ultraviolet and the Infrared Spectroscopy Depts. and the Biochemistry Dept. supervised, respectively, by A. P. Besancon, W. P. Blum and P. L. Harris, has been indispensable.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Arens, J. F. and D. A. van Dorr: Synthesis of Some Compounds Possessing Vitamin A Activity. Nature (London) 157, 190 (1946).
Arens, J. F. and D. A. van Dorf: A Cis C,5-Ketone, Related to Vitamin A. Recueil Tray. chin. Pays-Bas 66, 759 (1947).
Arens, J. F. and D. A. van Dorf: Synthesis of Vitamin A. Recueil Tray. chim. Pays-Bas 68, 604 (1949).
Arens, J. F. and D. A. van Dorf: Activity of “Vitamin A Acid” in the Rat. Nature (London) 158, 622 (1946).
Arens, J. F., D. A. van Dorf, G. van Dux and B. J. Brandt: A New Method for the Synthesis of α,β-Unsaturated Aldehydes. Preparation of β-Methylcinnesnaldehyde, Citral, and β-Ionylideneacetaldehyde. Recueil Tray. chim. Pays-Bas 67, 973 (1948).
Bacrarach, A. L. and E. L. Smith: Notes on the Chemistry of the Fat-Soluble Vitamins in Cod Liver Oil. Quart. J. Pharmac. Pharmacol. 1, 539 (1928).
Ball, S., T. W. Goodwin and R. A. Morton: Studies in Vitamin A. V. Preparation of Retinenel-Vitamin A Aldehyde. Biochemie. J. 43, 516 (1948).
Ball, S. and R. A. Morton: Studies in Vitamin A. X. Vitamin Al and Retinene1 in Relation to Photopic Vision. Biochemie J 45. 298 (1949).
Barda, R. K. and R. A. Morton: Studies in Vitamin A. XII. Whale Liver Analysis: Preparation of Kitol Esters. Biochemie. J. 45. 308 (1949).
Baxter, J. G. and C. D. Roasson: Crystalline Aliphatic Esters of Vitamin A. J. Aer. Chem. Soc. 64, 2407 (1942).
Baxter, J. G. and C. D. Roasson: Crystalline Vitamin A. J. A.er. chem. Soc. 64, 2411 (1942).
Boldingh, J., H. R. Cama, F. D. Collins, R. A. Morton, T. Gridgeman, O. Isler, M. Kofler, R. J. Taylor, A. S. Welland and T. Bradbury: Pure All-Trans Vitamin A Acetate and the Assessment of Vitamin A Potency by Spectrophotometry. Nature (London) 168, 598 (1951).
Braude, R., A. S. Foot, K. M. Henry, S. K. Kon,. S. Y. Thompson and T. H. Mead: Vitamin A Studies with Rats and Pigs. Biochemie. J. 35. 693 (1941).
Cawley, J. D.: Improved Vitamin A Products and Methods of Preparation Thereof. Brit. 579449, June 2 (1943)
Cawley, J. D.: Vitamin A Intermediate. Brit. 636935, May 10 (1950).
Cawley, J. D., C. D. Robeson, E. M. Shantz, L. Weisler and J. G. Baxter: Synthesis of Vitamin A Active Compounds Containing Repeated Isoprene Units., S. 2576103, November 27 (1951).
Cawley, J. D., C. D. Romrsox, L. Weisler, E. M. Shantz, D. Embree and J. G. Baxter: Crystalline Synthetic Vitamin A. Astracts, 112th Meeting American Chem. Soc., New York City, Y., September 15–19, 26C (1947).
Cawley, J. D., C. D. Romrsox, L. Weisler, E. M. Shantz, D. Embree and J. G. Baxter: Crystalline Synthetic Vitamin A and Neovitamin A. Science (New York) 107, 346 (1948).
Chatain, H. M. Debodard: A propos du dosage de la vitamine A: spectre ultraviolet, réaction de Carr-Price du kitol alcool, du kitol ester. C. R. hebd. Séances Acad. Sci. 233, 105 (1951).
Cheeseman, G. W. H., I. Heilbron, E. R. H. Joints, F. Sondheimer and B. C. L. Weedon: Studies in the Polyene Series. XXVIII. The Structure of the Cu-Aldehyde Derived from β-Ionone and its Use for the Synthesis of Norvitamin. A and Isovitamin A Derivatives. J. chem. Soc. ( London ) 1949, 1516.
Cheeseman, G. W. H., I. Heilbron, E. R. H. Jones and B. C. L. Weedon: Studies in the Polyene Series. XXXIV. The Synthesis of a CIS Alcohol Related to Vitamin A. J. chem. Soc. ( London ) 1949, 3120.
Clough, F. B., H. M. Kascher, C. D. Rossson and J. G. Baxter: Crystalline Kitol. Science (New York) 205, 436 (1947).
Davies, W. H., I. Heilbron, W. E. Joints and A. Lows: Studies in the Synthesis of Vitamin A. Part I. J. chem. Soc. (London) 1935, 584.
Distillation Products industries: Unpublished work.
Deuel, H. J. Jr.: The Lipids. Their Chemistry and Biochemistry. I. Chemistry. New York: Interscience. 1951.
Devine, J., R. F. Hunter and, E. Williams: The Preparation of fi-Carotene of a High Degree of Purity. Biochemie. J. 39, 5 (1945).
Embree, D.: Fat-Soluble Vitamins. Annu. Rev. Biochem. 1947, 323.
Embree, D. and E. M. Shantz: Kitol, a New Provitamin A. J. Aer. Chem. Soc. 65, 910 (1943)
Embree, D. and E. M. Shantz: A Possible New Member of the Vitamins Al and A, Group. J. Amer. chem. Soc. 65, 906 (1943)
Embree, D. and E. M. Shantz: Vitamin A Active Esters., S. 2434687, January 20 (1948).
Euler, H. V., P. Karrer: Über die biologische Wirksamkeit des Axerophtens und verwandter Kohlenwasserstoffe. Heiv. china. Acta 32, 461 (1949).
Farrar, K. R., J. C. Hamlet, H. B. Henbest and E. R. H. Jones: Elucidation of the Structure of Vitamin A, by Total Synthesis. Chem. and Ind. 1951, 49.
Fieser, L. F.: Absorption Spectra of Carotenoids; Structure of Vitamin A2. J. Org. Chemistry 15, 930 (1950).
Finholt, A. E., A. C. Bond Jr. and H. I. Schlesinger: Lithium Aluminum Hydride, Aluminum Hydride and Lithium Gallium Hydride, and Some of Their Applications in Organic Chemistry. J. Amer. chem. Soc. 69, 1199 (1947).
Gillam, A. E., I. Heilbron, W. E. Jones and E. Lederer. The Occurrence and Constitution of the 693 my Chromogen (Vitamin A?) of Fish Liver Oils. Biochemic. J. 32, 405 (1938).
Glover, J., T. W. Goodwin and R. A. Morton: Studies in Vitamin A. VI. Conversion in vivo of Vitamin A Aldehyde. Biochemic. J. 43, 109 (1948).
Golse, R., J. Gavarret, G. Demange: Synthèse de l’éther-oxyde méthylique de la vitamine A. Bull. Soc. chim. France 1950, 285.
Goss, G. C. and W. D. Mc Farlane: Oxidation of fl-Carotene with Osmium Tetroxide. Science (New York) 106, 375 (1947)
Gould, R. G. Jr. and A. F. Thompson Jr.: The Synthesis of Certain Unsaturated Compounds from β-Ionone and Tetrahydroquinone. J. Amer. chem. Soc. 57, 340 (1935)
Graham, W., D. A. van Dorp and J. F. Arens: Synthesis of a Cis Isomer of Vitamin A Aldehyde. Recueil Tray. chim. Pays-Bas 68, 609 (1949).
Gray, E. LeB.: Comparison of Vitamins A and A, by Distillation. J. biol. Chemistry 131, 317 (1939)
Gray, E. LeB. and J. D. Cawley: The Influence of the Structure on the Elimination Maximum. I. The Structure of Vitamin A8. J. biol. Chemistry 134, 397 (1940)
Hamano, S.: Physiologically Active Crystalline Esters of Vitamin A Sci. Pap. Inst. physic. chem. Res., Tokyo 28, 69 (1935).
Hanze, A. R., T. W. Conger, E. C. Wise and D. I. Weisblat: Crystalline Vitamin A Methyl Ether. J. Amer. chem Soc. 70, 1253 (1948).
Harper, S. H. and J. F. Oughton: Reformatsky Reactions with Methyl γ-Bromo-α,β-Dimethylacrylate. Chem. and Ind. 1950, 574.
Harris, P. L, S. R. Ames and J. H. Brinkman: Biochemical Studies on Vitamin A. IX. Biopotency of Neovitamin A in the Rat. J. Aer. chem. Soc. 73, 1252 (1951).
Heilbron, I.: Recent Developments in the Vitamin A Field J. chem. Soc. (London) 1948, 386.
Heilbron, I., R., Heslop, R. A. Morton, E. T. Webster, J. L. Rea and J. C. Drummond: Characteristics of Highly Active Vitamin A Preparations. Biochemie. J. 26, 1178 (1932).
Heilbron, I., A. W. Johnson, E. R. H. Jones and A. Spines: Studies in the Polyene Series. V. The Employment of 3-(2’:6’:6’-Trimethylcyclohexenyl)1-methylcrotonaldehyde for the Synthesis of Vitamin A and Analogues. J. Chem. Soc. (London) 1942, 727.
Heilbron, I., E. R. H. Jones and B. C. L. Weedon: Studies in the Polyene Series. XXIX. Ethoxyacetylenic Carbinols and Their Conversion to a,β-Unsaturated Aldehydes and Acids. J. chem. Soc. (London) 1949, 1823.
Heilbron, I., E. R. H. Jones, D. G. Lewis and B. C. L. Weedon: Studies in the Polyene Series. XXXI. The Synthesis of CIS- and C15-Acids Related to Vitamin A. J. chem. Soc. (London) 1949, 2023.
Heilbron, I., E. R. H. Jones and D. G. O’sullivan: Studies in the Polyene Series. XXIV. The C17-Acid and C18-Ketone Related to Vitamin A. J. chem. Soc. (London) 1946, 866.
Heilbron, I., E. R. H. Joxas and R. W. Richardson: Studies in the Polyene Series. XXV. Molecular Structure and Vitamin A Activity. Synthesis of a Biologically Active C17-Acid. J. chem. Soc. (London) 1949, 287.
Heilbron, I., E. R. H. Jones, D. G. Lawls, R. W. Richardson and B. C. L. Weedon: Studies in the Polyene Series. XXVII. The Synthesis of a Biologically Active C18 Acid. J. chem. Soc. ( London ) 1949, 742.
Heilbron, I., W. E. Jones, A. Lowe and H. R. Wright: Studies in the Synthesis of Vitamin A. Part II. J. chem. Soc. ( London ) 1936, 561.
Henbest, H. B.: Studies in the Polyene Series. XXXVII. Preparation of 3-Dehydro-β-Ionone and Some 3-Substituted β-Ionones. J. chem. Soc. ( London ) 1951, 1074.
Hickman, K. C. D.: Molecular Distillation. Apparatus and Methods. Ind. Engng. Chem. 29, 968 (1937).
Hickman, K. C. D.: State of the Vitamins in Certain Fish Liver Oils. Ind. Engng. Chem. 29, 1107 (1937).
Holmes, H., and R. E. Corset: The Isolation of Crystalline Vitamin A. J. A.er. chem. Soc. 59, 2042 (1937)
Hubbard, R. and G. Wald: Cis-trans Isomers of Vitamin A and Retinene in Vision. Science (New York) 115, 60 (1952).
Huisman, H. O.: Investigations in the Vitamin A Series. I. A New Synthesis of Vitamin A Acid and Vitamin A. Recueil Tray. chim. Pays-Bas 69, 851 (1950).
Hunter, R. F.: Carotenoids and Vitamin A. Research 3, 453 (1950).
Hunter, R. F. and, E. Williams: Chemical Conversion of β-Carotene into Vitamin A J. chem. Soc. ( London ) 1945, 554.
Inhoffen, H. H., F. Bohlmann: 1939 Synthesen in der Carotinoid-Chemie seit. Fortschr. chem. Forschg. 1, 175 (1949)
Inhoffen, H. H., F. Bohlmann, K. Bartram: Synthesen in der CarotinoidReihe. I. Kondensationen von β-Jonon und homologen Ketonen mit Oxalester. Liebigs Ann. Chem. 561, 13 (1948).
Inhoffen, H. H., F. Bohlmann, K. Bartram, H. Pommer: XI. Totalsynthese des β-Carotins. Chemiker-Ztg. 74, 285 (1950).
Inhoffen, H. H., F. Bohlmann, M. Bohlmann: Synthesen in der Carotinoid Reihe. VI. Darstellung der Vitamin-A-Säure und einer isomeren C20-Saure. Liebigs Ann. Chem. 568, 47 (1950).
Inhoffen, H. H., H. Pommer, F. Bohlmann: XII. Zweite Synthese des β-Carotins. Chemiker-Ztg. 74, 309 (1950).
Inhoffen, H. H., H. Pommer, F. Bohlmann: Synthesen in der Carotinoid-Reihe. XIV. Aufbau des β-Carotins. Liebigs Ann. Chem. 569, 237 (1950).
Inhoffen, H. H., H. Pommer, F. Westphal: Synthesen in der CarotinoidReihe. XVI. Eine weitere Synthese des β-Carotins. Liebigs Ann. Chem. 570, 69 (1950).
Inhoffen, H. H., H. Siemer: Synthetische Chemie der Carotinoide. Fortschr. Chem. Organ. Naturstoffe 9, 1 (1952).
Ishixawa, S. and T. Matsuura: Synthesis of Aldehydic Isomers of Methylionone. Sci. Rep. Tokyo Bunrika Daigaku, Sect. A 3, No. 60, 173 (1937).
Isler, O.: Über Synthesen in der Vitamin A-Reihe. Chimia 3, 150 (1949).
Isler, O.: Swiss 254948.
Isler, O.: Swiss 26, 888.
Isler, O.: Die Chemie des Vitamin A. Chimia 4, 103 (1950).
Isler, O.: Leaflet distributed, American Chemical Society Meeting, New York City, Y., September (1951).
Isler, O., W. Huber, A. Roxco, M. Kofler: Synthese des Vitamin A. Heiv. chim. Acta 30, 1911 (1947).
Isler, O., M. Kofler, W. Huber, A. Roxco: Synthese von Vitamin AMethyläther. Experientia 2, 31 (1946).
Isler, O., A. Ronco, W. Guex, C. Hindley, W. Huber, K. Dialer, M. Kofler: Über die Ester und Äther des synthetischen Vitamins A Heiv. chim. Acta 32, 489 (1949).
Johnson, A. W.: Recent Advances in Science; Organic Chemistry, Science Progress 36, 112, 496 (1948).
Karrer, P.: Neuere Fortschritte auf dem Gebiete der Carotinoide und des Vitamins A. Osterr. Chemiker-Ztg. 49, 2115 (1948).
Karrer, P., J. Benz: Axerophten, der dem Vitamin A zugrunde liegende Kohlenwasserstoff. Heiv. chim. Acta 31, 1048 (1948).
Karrer, P., J. Benz: Eine neue Synthese des Desmethylaxerophtens. Heiv. chim. Acta 31, 1607 (1948).
Karrer, P., J. Benz: Zur Synthese des Axerophtens. II. Mitteilung. Helv. chim. Acta 32, 232 (1949)
Karrer, P., C. H. Eugster: Darstellung und einige Umsetzungen des Octadien-(3,5)dions-(2,7). Heiv. chim. Acta 32, 1934 (1949).
Karrer, P., C. H. Eugster: Totalsynthese des β-Carotins. Helv. Chim. Acta 33, 1172 (1950).
Karrer, P., C. H. Eugster: Synthèse totale du β-carotène. C. R. hebd. Séances Acad. Sci. 230, 1920 (1950).
Karrer, P., A. Geiger, E. Bretscher: Über das sog. Vitamin A. Helv. chini. Acta 24, 161E (1941).
Karrer, P., E. Jucker: Die Konstitution des „574 Chromogens“ oder Hepaxanthins aus Lebertran. Heiv. chini. Acta 28, 717 (1945)
Karrer, P., E. Jucker: Über Vitamin A-Epoxyd (Hepaxanthin). II. Heiv. chim. Acta 30, 559 (1947).
Narrer, P., E. Jucker, E. Schick: Synthese der Vitamin-A-Säure und der entsprechenden, den a- Jononkohlenstoffring enthaltenden Verbindung (3, 7-Dimethyl-9-[I’, I’, 3’-trimethyl-c.-hexen-3’-y1–2]-nonatetraen-[2,4,6, 8]-carbonsäure). Helv. chim Acta 29, 704 (1946).
Karrer, P., R. Morf, K. Schöpp: Zur Kenntnis des Vitamins A aus Fischtranen. Heiv. chim. Acta 14, 1036–1431 (1931).
Karrer, P., H. Salomon, R. More, O. Walker: Über mehrfachungesättigte, den β-oder α-Jonon-Kohlenstoffring enthaltende Verbindungen. Heiv. chim. Acta 25, 878 (1932).
Karrer, P., P. Schneider: Beitrag zur Konstitution des Vitamins A. Helv. chim. Acta 33, 38 (1950).
Karrzr, P., R. Scewyzer: Überführung von Vitamin Ain Anhydrovitamin A und ein Carotinoid, wahrscheinlich identisch mit β-Carotin. Rely. chim. Acta 35, 50–55 (1948).
Kipping, F. B. and F. Wild: Synthesis of Vitamin A Methyl Ether. Chem. and Ind. 1939, 802.
Kush, R., C.C.J.O. R. Morris: Synthese von Vitamin A. Ber. Dtsch. chem. Ges. 70, 853 (1937)
Lederer, E. A. and V. A. Roaaxova: Studies on Vitamin A of Fish-Liver Oils. I. An Abnormal Reaction of CARR and PRICE. Biokimiya (U. S. S. R.) 2, 293 (1937)
Linnsu, W. H. and C. C. Suez: Synthesis of the Benzene Analog of Vitamin A. J. Pharmac. Pharmacol. 1, 971 (1949).
Mean, T. H.: Crystalline Esters of Vitamin A. I. Preparation and Properties. Biocltemic. J. 33, 589 (1939).
Mauzzar, P.: Sur la véritable formule de l’axérophtène. C. R. hebd. Séances Acad. Sci. 237, 206 (1948).
Mauzzar, P.: Des carotènes aux rétinènes. Revue internationale de Vitaminologie 23, 31 (1951).
Meunier, P., R. Dulou, A. Vinet: Sur les conditions de formation, la constitution de la vitamine A dite cycliséer. Bull. Soc. Chini. biol. 25, 371 (1943)
Meunier, P., R. Fsrrando: Activité biologique du chromogène k 560 mer obtenu dans l’oxydation permanganique de l’axérophtol. Bull. Soc. Chini. Biol. 31, 227 (1949)
Meunier, P., A. Guérillot-Vinet, J. Jouanneteau, M. Gourevitcb: Sur les corps obtenus per action progressive de l’acide chlorohydrique sur la vitamine A, leur activité biologique. C. R. hebd. Séances Acad. Sci. 226, 128 (1948)
Meunier, P., J. Jouanneteau: Sur un congénère de l’axérophtal (rain-aldéhyde). Bull. Soc. Chini. biol. 30, 185 (1948).
Meunier, P., J. Jouanneteau: Recherches sur l’isomérie cis-trans dans la série de la vitamine A (axérophtal). Bull. Soc. Chim. biol. 30, 260 (1948).
Meunier, P., J. Jouanneteau, R. Ferrando: Sur Is toxicité pour le Rat blanc d’un nouveau dérivé d’oxydation de la vitamine A. C. R. hebd. Séances Acad. Sci. 230, 140 (1950).
Meunier, P., J. Jouanneteau, G. Zwingelstein: Sur la coupure oxydante du β-carotène en rétinène (axérophtal) par Mno. C. R. hebd. Séances Acad. Sci. 235, 1170 (1950).
Meunier, P., J. Jouanneteau, G. Zwingelstein: La coupure oxydante du lycopène par MnO, l’activité biologique du rétinène, ainsi obtenu. C. R. hebd. Séances Acad. Sci. 231, 1570 (1950).
Meunier, P., R. Mallein, J. Jouanneteau: Recherches chimiques dans la série du rétinène (axérophtal). I. Identification du congénère du rétinène responsable de l’halochromie k 56o me. Bull. Soc. Chim. Biol. 35, 965 (1949).
Meunier, P., G. Zwingelstein, J. Jouanneteau, R. Mallein: Sur la structure exacte du dérivé k action antivitaminique A obtenu par oxidation de l’axérophtol. C. R. hebd. Séances Acad. Sci. 230, 1323 (1950).
Milas, A.: Vitamin A., S. 2369156, Feb. 13 (1945).
Milas, A.: Synthesis of Biologically Active Vitamin A Substances. Science (New York) 103, 581 (1946).
Milas, A.: The Synthesis of Vitamin A and Related Products. Vitamins and Hot mones 5, 1 (1947)
Milas, A.: Vitamin A Acid and Esters., S. 2424994, August 5 (1947).
Milas, A.: Dimethylamino Vitamin A., S. 2507802, May 16 (1950).
Milas, A., P. Davis, I. Beltc and D. A.Fles: Synthesis of β-Carotene. J. Amer. chem. Soc. 72, 4844 (1950).
Milas, A. and T. M. Harrington: New Synthesis of I-(2’,6’,6’-Trimethylcyclohexen-x’-y’)3-methyl-x,3,5-trien-7-one (C18-ketone). J. Amer. chem. Soc. 69, 2247 (1947): cf. 70, 4275 (1948).
Milas, A., S. W. Lee, E. Sakal, H. C. Wohlers, S. Mcdonald, F. X. Grossi and H. F. Wright: Synthesis of Products Related to Vitamin A. IV. The Application of the Darzens Reaction to β-Ionone. J. A.er. chem. Soc. 70, 1584 (1948)
Milas, A., S. W. Lee, C. Schuerch, R. O. Edgerton, J. T. Plati, F. X. Grossi, Z. Weiss and M. A. Campbell Synthesis of Products Related to Vitamin A. V. The Synthesis of [x-(2’,6’,6-trimethylcyclohexen-I’-yl)3,7-dimethyldeca-1,3,5,7-tetraenyl]-Io-ethyl Ether. J. Amer. chem. Soc. 70, 1591 (1948).
Milas, A., E. Sakal, J. T. Plati, J. T. Rivers, J. K. Gladding, F. X. Grossi, Z. Weiss, M. A. Campbell and H. F. Wright: Synthesis of Products Related to Vitamin A. VI. The Synthesis of Biologically Active Vitamin A Ethers. J. A.er. chem. Soc. 70, 1597 (1948).
Morton, R. A.: Chemical Aspects of the Visual Process. Nature (London) 153, 69 (1944)
Morton, R. A., M. K. Salah and A. L. Stubbs: Retinene and Vitamin A,. Nature (London) 159, 744 (1947)
Oroshnik, W.: A Synthesis of Vitamin A Methyl Ether—Preliminary Report. J. Amer. chem. Soc. 67, 1627 (1945)
Oroshnik, W.: Ethynyl Carbinols., S. 2425201, August 5 (1947)
Oroshnik, W., G. Karmas and A. D. Mebane: Synthesis of Polyenes. I. Retrovitamin A Methyl Ether, Spectral Relationships between the β-Ionolidene and Retroionolidene Series. J. Amer. chem. Soc. 74, 295 (1952).
Oroshnik, W. and A. D. Mebane: The Nef Reaction with a,β-Unsaturated Ketones. J. Amer. chem. Soc. 71, 2062 (1949).
Ortho Pharmaceutical Company: Brit. 630865.
Ortho Pharmaceutical Company: Brit. 653679.
Petrow, V. and O. Stephenson: The Synthesis of 4-Carboxyvitamin A Acid. J. chem. Soc. (London) 1950, 1310.
Preobrazhenskii, A. and I. A. Rubsxov: Syntheses in the Field of Vitamin A. III. Synthesis of β-Ionylideneacetaldehyde. J. gen. Chem. (USSR.) 18, 1719 (1948)
Robeson, C. D.: Esterification of Polyene Acids., S. 2583594 (January 29, 1952).
Robeson, C. D. and J. G. Baxter: Neovitamin A. J. A.er. chem. Soc. 69, 136 (1947)
Robeson, C. D. and C. C. Eddinger: Unsaturated Aldehydes., S. 2507647, May 16 (1950).
Salah, M. K. and R. A. Morton: Crystalline Retinae. Biochemic. J. 43, L6 (1948).
Schwarzkopf, O., H. J. Cahnmann, A. D. Lewis, J. Swidinsky and H. M. Wüest: Synthesis of Vitamin A. A Synthesis of Vitamin A Acid Ester, Its Conversion to Vitamin A Acid Ester and Its Reduction to Vitamin As. Abstracts, x 15th Meeting American Chem. Soc., San Francisco, California. March 27—April x, x I C (1949)
Schwarzkopf, O., H. J. Cahnmann, A. D. Lewis, J. Swidinsky and H. M. Wüest: Zur Synthese des Vitamins A. I. Eine neue Methode zur direkten Darstellung von Vitamin A von hoher biologischer Wirksamkeit. Helv. chim. Acta 32, 443 (1949).
Shantz, E. M.: Isolation of Pure Vitamin A2. Science (New York) 108, 417 (1948).
Shantz, E. M.: Rehydrovitamin A, the Compound Formed from Anhydrovitamin A in vivo. J. biol. Chemistry 182, 515 (1950).
Shantz, E. M. and J. H. Brinkman: Biological Activity of Pure Vitamin A2. J. biol. Chemistry 183, 467 (1950).
Shantz, E. M., J. D. Cawley and F. B. Clough: The Structure of the Ionylideneacetic Acids. Unpublished report. (Distillation Products industries.)
Shantz, E. M., J. D. Cawley and, D. Embree: Anhydro (“Cyclized”) Vitamin A. J. Amer. chem. Soc. 65, 901 (1943)
Shantz, E. M., C. D. Robeson and H. M. Kascher: Dehydration and Isomerization of Straight-Chain Conjugated Polyene Esters and Acids., S. 2576104, Nov. 27 (1951).
Sobotka, H. and E. Bloch: Polyene Syntheses. Chem. Reviews 34, 435 (1941).
Sobotka, H., E. Bloch and D. Glick: Studies on Innone. I. Cleavage of Ethyl Ionylidene Acetate. J. Amer. chem. Soc. 65, 1961 (1943).
van Dorp, D. A. and J. F. Arens: Biological Activity of Vitamin A Acid. Nature (London) 158, 60 (1946).
van Dorp, D. A. and J. F. Arens: The Synthesis of “Vitamin A Acid”, A Biologically Active Substance. Recueil Tray. chim. Pays-Bas 65, 338 (1946).
van Dorp, D. A. and J. F. Arens: Synthesis of Vitamin A Aldehyde. Nature (London) 160, 189 (1947)
van Dorp, D. A. and J. F. Arens: Condensation Reaction of Ketones with Hydroxymaleic Anhydride. Transformation of the Condensation Products into α,β-Unsaturated Aldehydes. Recueil Tray. chim. Pays-Bas 67, 459 (1948).
Wald, G.: The Chemical Evolution of Vision. The Harvey Lectures 41, 117 (1945–1946).
Wald, G.: Synthesis from Vitamin Al of Retinene and of a New 545 mu Chromogen Yielding Light-Sensitive Products. J. gen. Physiol. 31, 489 (1947–1948).
Wald, G.: The Enzymic Reduction of the Retinenes to the Vitamins A Science (New York) 109, 482 (1949)
Wald, G.: Interconversion of the Retinenes and Vitamins A in vitro. Biochem. Biophys. Acta 4, 215 (1950).
Wald, G. and R. Hubbard. Reduction of Retinenel to Vitamin Al in vitro. J. gen. Physiol. 32, 367 (1948–1949).
Weedon, B. C. L. and R. J. Wooers: Studies in the Polyene Series. XXXVII. The Synthesis of Phenyl Analogues of Vitamin A Acids and Vitamin A. J. chem. Soc. ( London ) 1951, 2687.
Wendler, L., C. Rosenslum and M. Tishler: The Oxidation of β-Carotene. J. Amer. chem. Soc. 72, 234 (1950).
Wendler, L., H. L. Slates and M. Tishler: Synthesis of Vitamin A. J. A.er. chem. Soc. 71, 3267 (1949)
Wendler, L., H. L. Slates, R. Trenner and M. Tishler: Synthesis of Vitamin A. J. A.er chem. Soc. 73, 719 (1951).
Young, W. G., L. J. Andrews and S. J. Cristol: Polyenes I. The Synthesis and Absorption Spectra of the Ionylideneacetones and Related Compounds. J. Amer. chem. Soc. 66, 520 (1944).
Zechmeister, L.: Stereoisomeric Provitamins A. Vitamins and Hormones 7, 57 (1949)
Zeile, K., H. Meyer: Über einige Umsetzungen von Propargylderivaten. Ber. dtsch. chem. Ges. 75, 356 (1942).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1952 Wien · Springer-Verlag
About this chapter
Cite this chapter
Baxter, J.G. (1952). Synthesis and Properties of Vitamin A and Some Related Compounds. In: Zechmeister, L. (eds) Fortschritte der Chemie Organischer Naturstoffe/Progress in the Chemistry of Organic Natural Products/Progrès Dans La Chimie Des Substances Organiques Naturelles. Fortschritte der Chemie Organischer Naturstoffe/Progress in the Chemistry of Organic Natural Products/Progrès Dans La Chimie Des Substances Organiques Naturelles, vol 9. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7169-1_2
Download citation
DOI: https://doi.org/10.1007/978-3-7091-7169-1_2
Publisher Name: Springer, Vienna
Print ISBN: 978-3-7091-7171-4
Online ISBN: 978-3-7091-7169-1
eBook Packages: Springer Book Archive