Reaction of β-Carotene with N-Bromosuccinimide: The Formation and Conversions of Some Polyene Ketones

Petracek, F. J.; Ƶechmeister, L.

doi:10.1021/ja01588a044

Cited by 80 publications

(21 citation statements)

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“…The value of 38 is intermediate between those of luteid (11) and "hydroxy-a-carotene" (57) ; it is in close agreement with values of 38-39 previously obtained ( 4 ) for monoether (epoxide and furanoxide) mono1 fractions. This indicates that the main fraction above is the 3'-methyl ether of lutein.…”

Section: Resultssupporting

confidence: 89%

“…When lutein was treated with hydrochloric acid in methanol, and the recovered carotenoids subjected to countercurrent distribution in a Craig apparatus with the system petroleum ether-99% methanol (I), two fractions were obtained with Nloo values (tube number of maximum calculated per 100 transfers) of 10 (unchanged lutein, 14%) and 38 (85%), respectively. The value of 38 is intermediate between those of luteid (11) and "hydroxy-a-carotene" (57) ; it is in close agreement with values of 38-39 previously obtained ( 4 ) for monoether (epoxide and furanoxide) mono1 fractions. This indicates that the main fraction above is the 3'-methyl ether of lutein.…”

Section: Effect Of Iodine In Light On "Hydroxy-a-carotene" and Relatesupporting

confidence: 89%

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ON THE STRUCTURE OF “HYDROXY‐_α‐CAROTENE” FROM ORANGE JUICE

Curl

1956

Journal of Food Science

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I n an examination of the carotenoids of Valencia orange juice, an hydroxy-a-carotene-like substance was found (1) as a minor constituent occurring to the extent of around 2 to 3% of the total carotenoids; similar fractions have also been obtained from orange peel ( 4 ) , tangerines (pulp and peel), Ruby red grapefruit (pulp and peel), peaches and apricots (2), in amounts of 1% or less of the total carotenoids. Similar substances had been obtained previously by other workers from severaI sources, including Mycobacterium phlei (6), leaves (13), yellow corn grain (15), and corn seedlings (20). It appears that " hydroxy-a-carotene " is a widespread minor carotenoid constituent, but a sufficiently rich source has not yet been found so that the substance could be obtained in crystalline form. Hydroxya-carotene is not discussed in the monographs of Karrer and Jucker (7) or Goodwin (5); the only mention is a reference to its occurrence in Zea mays in the former. The present communication gives further information on ' ' hydroxy-a-carotene, " including indirect evidence indicating that it is not a provitamin A. EXPERIMENTAL METHODSThe experimental methods used in countercurrent distribution and chromatography were previously described (1).Iodine treatment. Ten ml. of a carotenoid solution in petroleum ether (or benzene) having a n adsorbance at the principal maximum of around 1.5, measured in a one-em. cell in a Cary recording spectrophotometer, was treated with 0.2 ml. of a 0.001% solution of iodine in petroleum ether (or benzene) and then exposed to light from a daylight fluorescent lamp a t approximately 260 foot candles, for 30 minutes. Spectral adsorption curves were then run within a few minutes.Acid treatment. Carotenoid solutions were evaporated in vacuo and the residue dissolved in a solution of hydrochloric acid in methanol (1 volume of concentrated acid plus 9 volumes of methanol). After standing a t room temperature for 10 minutes, an excess of potassium hydroxide in methanol was added, and the solution worked up as previously described (3). The product was rechromatographed and spectral absorption curves were run on the band or bands. RESULTS AND DISCUSSIONThe ((hydroxy-a-carotene" from orange juice (1) was obtained on countercurrent distribution of the saponified carotenoids (unsaponifiable fraction) with the system petroleum ether-99% methanol in the same fraction as cryptoxanthin (3-hydro~y-P-carotene)~ indicating the presence of one hydroxyl group and the probable absence of other oxygen atoms such as cyclic ether groups which would change the distribution coefficient. On chromatography on columns of magnesia (Westvaco No. 2642) plus filter aid, and eluting with a solution of 0.5% ethanol in petroleum ether, 689

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Section: Resultssupporting

confidence: 89%

Section: Effect Of Iodine In Light On "Hydroxy-a-carotene" and Relatesupporting

confidence: 89%

ON THE STRUCTURE OF “HYDROXY‐_α‐CAROTENE” FROM ORANGE JUICE

Curl

1956

Journal of Food Science

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“…Surmatis et al (781) presented a synthesis of canthaxanthin from vitamin A alcohol. The absence of provitamin A activity was noted both in synthetic canthaxanthin and in canthaxan thin isolated from Corynebacterium michiganese by Petracek and Zechmeister (633,634). However, in retinol-depleted guppies and platies, canthaxanthin, as well as /3-carotene, increased the retinol content of the liver, according to Olson (616).…”

Section: Canthaxanthin For Yolk Pigmentationmentioning

confidence: 93%

Oxycarotenoids in Poultry Feeds

Marusich¹,

Bauernfeind²

1981

Carotenoids as Colorants and Vitamin a Precursors

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“…Canthaxanthin was synthesized from /3-carotene by Zechmeister in 1956 23 and by Karrer in 1958. 24 The first complete synthesis of canthaxanthin was devised by Isler et al 25 Isler and co-workers reported a synthesis of canthaxanthin from 15,15'-dehydro-/3-carotene in 1963 26 which was developed into the first industrial synthesis.…”

Section: Canthaxanthinmentioning

confidence: 99%

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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Reaction of β-Carotene with N-Bromosuccinimide: The Formation and Conversions of Some Polyene Ketones

Cited by 80 publications

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ON THE STRUCTURE OF “HYDROXY‐_α‐CAROTENE” FROM ORANGE JUICE

ON THE STRUCTURE OF “HYDROXY‐_α‐CAROTENE” FROM ORANGE JUICE

Oxycarotenoids in Poultry Feeds

Carotenoids as food colorants

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Reaction of β-Carotene with N-Bromosuccinimide: The Formation and Conversions of Some Polyene Ketones

Cited by 80 publications

References 0 publications

ON THE STRUCTURE OF “HYDROXY‐α‐CAROTENE” FROM ORANGE JUICE

ON THE STRUCTURE OF “HYDROXY‐α‐CAROTENE” FROM ORANGE JUICE

Oxycarotenoids in Poultry Feeds

Carotenoids as food colorants

Contact Info

Product

Resources

About

ON THE STRUCTURE OF “HYDROXY‐_α‐CAROTENE” FROM ORANGE JUICE

ON THE STRUCTURE OF “HYDROXY‐_α‐CAROTENE” FROM ORANGE JUICE