Synthesen in der Carotinoid‐Reihe. 15. Mitteilung Synthesen in der β‐Carotinal‐ und β‐Carotinal‐Reihe

Rüegg, R.; Montavon, M.; Ryser, G.; Saucy, G.; Schwieter, Ulrich; Isler, O.

doi:10.1002/hlca.19590420328

Cited by 84 publications

(33 citation statements)

References 6 publications

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“…20 The total synthesis of beta-apo-8'-carotenal by the Roche group 21 ' 22 made possible a thorough study of this interesting carotenoid. A synthesis from Ci9-aldehyde was reported by Isler and co-workers in 1959 22 which was developed into the first industrial preparation of this carotenoid.…”

Section: B Beta-apo-8'-carotenalmentioning

confidence: 96%

Carotenoids as food colorants

Gordon

Bauernfeind

Furia³

1983

C R C Critical Reviews in Food Science and Nutrition

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The carotenoids are a chemically related group of pigments which occur widely and abundantly in nature. Fruits, vegetables and vegetable oils, dairy products, leaves, shrimp, lobster, the plumage of exotic birds, all contain carotenoids. Chemically, the carotenoids may be divided into carotenes, made up of carbon and hydrogen only, and oxycarotenoids containing oxygen in addition to carbon and hydrogen. The use of carotenoid-containing plant extracts for coloring foods has been practiced for centuries and continues today. Advances in chemical synthesis resulted in the complete laboratory synthesis of beta carotene in 1950. Since then the commercial synthesis of several carotenoids has been accomplished. In the U.S. three of these commercially synthesized carotenoids, beta-carotene, beta-apo-8'-carotenal, and canthaxanthin, are accepted color additives for use in foods and are exempt from certification. These three carotenoids are also widely accepted for food use in other countries. This paper deals with the chemistry and synthesis of these three carotenoids, with special emphasis on their numerous commercially available market forms and their characteristics, and on the application of these carotenoids in the coloring of food products.

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Section: B Beta-apo-8'-carotenalmentioning

confidence: 96%

Carotenoids as food colorants

Gordon

Bauernfeind

Furia³

1983

C R C Critical Reviews in Food Science and Nutrition

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“…However, the FT-n.m.r. Treatment of the resulting glycol (24) with stannous chloride and hydrochloric acid yielded tetrasubstituted didehydro [14]annulene (25). As previously mentioned, 18-membered cyclic glycols (9) were obtained by oxidative coupling of bis-ethynyl alcohols (8) in unexpectedly high yields.…”

Section: Introductionmentioning

confidence: 91%

“…l,8-Didehydro [14]annulene (1) obtained by Sondheimer 1-4 holds a unique position in a wide variety of dehydroannulenes, i.e. it contains formal acetylenic and cumulenic linkages in the cyclic system and classical equivalent Kekulé structures (la and lb) can be written in contrast to la lb 2 F. Sondheimer ordinary dehydroannulenes containing only acetylenic bond(s) in which no equivalent resonance structures can be drawn.…”

Section: Introductionmentioning

confidence: 99%

‘Acetylene–cumulene’ Dehydroannulenes

Nakagawa

1975

The Chemistry of Nonbenzenoid Aromatic Compounds –II

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The synthesis of tetrasubstituted tetradehydro [18]-and [22]annulenes containing a diacetylene and a hexapentaene unit has been accomplished by reductive dehydroxylation of corresponding 18-membered and 22-membered cyclic glycols. On the basis of these studies, a general method of preparation of tetrasubstituted didehydro[4w + 2]annulenes containing an acetylene and a butatriene unit has been developed. The didehydro[4n + 2]annulenes (n = 3 ~ 7) were found to be diatropic and to have high conformational stability. The n.m.r. spectral properties of the didehydroannulenes have been discussed. The synthesis of didehydro[14]annulenes annelated with naphthalene or benzene has been achieved, and the effect of annelation on π-electron delocalization of the annulene ring has been discussed.

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“…Ausbeute erhalten. Das UV/VIS-Spektrum stimmt sehr gut mit 12'-Apo-/l-carotin-l2'-al [4] uberein. Bei RT.…”

Section: R=hunclassified

“…zeigt 5 einen nur geringen Cotton-Effekt, der sich wie bei anderen Verbindungen rnit einer 4-Hydroxy-B-Endgruppe durch Abkuhlen wesentlich verstarken Iasst [l]; s. Kup. 4.…”

Section: R=hunclassified

Synthesen von optisch aktiven Carotinoiden mit einer (R)‐4‐Hydroxy‐β‐Endgruppe

Haag

Eugster

1985

Helvetica Chimica Acta

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Synthesis of Optically Active Carotenoids with (R)‐4‐Hydroxy β‐End Groups We describe the synthesis of optically active iso‐β‐kryptoxanthin (12; (R)‐β,β‐caroten‐4‐ol), iso‐α‐kryptoxanthins 14 ((4R,6′RS)‐β,ε‐caroten‐4‐ol) and 16 ((4R,6′R)‐β,ε‐caroten‐4‐ol), 4′‐hydroxyechinenone (18; (R)‐4′‐hydroxy‐β,β‐caroten‐4‐one), and isorubixanthin (20; (R)‐β,ω,‐caroten‐4‐ol), their 400‐MHz‐1H‐NMR spectra, CD spectra and HPLC behaviour.

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Synthesen in der Carotinoid‐Reihe. 15. Mitteilung Synthesen in der β‐Carotinal‐ und β‐Carotinal‐Reihe

Cited by 84 publications

References 6 publications

Carotenoids as food colorants

Carotenoids as food colorants

‘Acetylene–cumulene’ Dehydroannulenes

Synthesen von optisch aktiven Carotinoiden mit einer (R)‐4‐Hydroxy‐β‐Endgruppe

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