Helvetica Chimica Acta

1931

DOI: 10.1002/hlca.19310140422

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Pflanzenfarbstoffe XXXIV. Dihydro‐lycopin

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Derivatives Of Lutein (1a)2

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Cited by 17 publications

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“… 4 A major breakthrough occurred in 1931 when the chemical structures for β,β-carotene and retinol (its all-trans isomer now known as vitamin A) were determined by Karrer and colleagues. 5 But, it was Wald who discovered that retinol derivatives constitute the chemical basis of our vision, 6 a contribution subsequently recognized by a Nobel Prize award in 1967. In 1950–1960, a variety of vitamin A metabolic transformations, including oxidation/reduction and esterification, were elucidated by Olson, 7 − 20 Goodman, 21 − 32 Chytil and Ong, 33 − 41 and Norum and Blomhoff.…”

Section: Introductionmentioning

confidence: 99%

Chemistry of the Retinoid (Visual) Cycle

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2013

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No abstract

“… 4 A major breakthrough occurred in 1931 when the chemical structures for β,β-carotene and retinol (its all-trans isomer now known as vitamin A) were determined by Karrer and colleagues. 5 But, it was Wald who discovered that retinol derivatives constitute the chemical basis of our vision, 6 a contribution subsequently recognized by a Nobel Prize award in 1967. In 1950–1960, a variety of vitamin A metabolic transformations, including oxidation/reduction and esterification, were elucidated by Olson, 7 − 20 Goodman, 21 − 32 Chytil and Ong, 33 − 41 and Norum and Blomhoff.…”

Section: Introductionmentioning

confidence: 99%

Chemistry of the Retinoid (Visual) Cycle

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2013

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“…The constitution of zeaxanthin was elucidated around 1930, again by Karrer et al, by classical degradation methods and mostly parallel to that of lutein [5] [14]. A first synthesis of zeaxanthin, probably a mixture of rac-and meso-forms, was published by Isler et al in 1956 [18].…”

Section: Derivatives Of Lutein (1a)mentioning

confidence: 99%

“…± Zeaxanthin ( (3R,3R')-b,b-carotene-3,3'-diol; 2a) was first isolated by Karrer et al [5], and named according its occurrence in yellow corn (Zea mays). The elucidation of the constitution of zeaxanthin was conducted parallel to that of lutein [5] [14]. Around the same time, crystalline physalien was isolated from calyces of Physalis alkekengi [15], but only later recognized as being the palmitic ester of zeaxanthin [16] [17].…”

Section: Derivatives Of Lutein (1a)mentioning

confidence: 99%

“…Plane 1i 2b C(7)ÀC(8)ÀC(9)ÀC(10) 5.1(7) 2.3(7) C(8)ÀC(9)ÀC(10)ÀC (11) 7.7(7) 2.5(7) C(9)ÀC(10)ÀC(11)ÀC (12) 8.1(7) 2.9(8) C(10)ÀC(11)ÀC(12)ÀC (13) 10.5(7) 3.8(8) C(11)ÀC(12)ÀC(13)ÀC (14) 13.3(7) 6.4(7) C(12)ÀC (13)ÀC (14)ÀC (15) 14.0(7) 7.3(8) C(13)ÀC (14)ÀC (15)ÀC (35) 15.0(7) 6.3(8) C (14)ÀC (15)ÀC (35)ÀC (34) 16.3 (7) 6.4(8) C(26)ÀC (27)ÀC (28)ÀC (29) 28.2(7) 8.2(8) C(27)ÀC (28)ÀC (29)ÀC (30) 19.2(7) 4.6(7) C(28)ÀC (29) (15) 17.7(7) 7.4(8) Fig. 2.…”

Section: Simplifiedunclassified

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Confirmation of the Structures of Lutein and Zeaxanthin

2004

Helvetica Chimica Acta

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A series of new esters of lutein (1a) have been prepared with the aim of confirming the structure of lutein via an X-ray crystal-structure analysis. Although well crystallized, only one of the derivatives, the (À)-(1R)-menthyl carbonate (1i) proved to be useful for a complete structure analysis. The same derivative of zeaxanthin (2a) also allowed its crystal structure to be determined. Both analyses represent the first successful X-ray crystal structure analyses of the most important xanthophylls. At the same time, they confirm both the constitution and absolute configuration of 1a and 2a that had been deduced earlier by classical methods.

“…by Euler [1931], Karrer, Morf andSchopp [1931, 1, 2] andEuler andKarrer [1931], although the differences may to some extent be due to different methods of conducting the feeding experiments.…”

mentioning

confidence: 99%

Characteristics of highly active vitamin A preparations

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et al. 1932

Biochemical Journal

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IN a series of papers emanating from these laboratories during the past five years unequivocal spectroscopic data for vitamin A have been established, and the ground has been cleared for a final comprehensive attack on the problem of isolating the vitamin and establishing its constitution. The present communication embodies the results of work carried out during the last 18 months, and leads us to the view that a definite solution of the problem is now in sight, a view supported by the recent highly important and illuminating publications of Karrer, Morf and Sch6pp [1931, 1, 2], to which further reference will be made later. Vitamin A, both in liver oils and concentrates, exhibits a broad continuous absorption band in the ultraviolet , extending from 260 to 380 m,u, and exhibiting a maximum near 328 m,. The intensity of this band can easily be measured and used as a definite quantitative test for the potencies of oils and concentrates. Vitamin A also shares with a variety of polyene substances the power of giving a blue solution with a saturated solution of anhydrous antimony trichloride in chloroform. This colour test gains in specificity when the spectral absorption of the blue solution can be accurately described. As a matter of convenience attention may be concentrated on the points of maximum absorption described in terms of intensity and spectral location'. Thus the blue solution obtained with vitamin A exhibits two maxima at 617 and 583 mu respectively, the former being generally much more intense than the latter, which it tends to mask. In unsaponified oils the maxima are displaced to 606 and 573 m, respectively, and here the longer wavelength absorption 1 The notation used in this paper is necessarily a little different from that employed in spectroscopic studies on pure substances. The usual method is to state the maximum molecular extinction coefficient e, defined by E =log Io/I =ecd. (Io is intensity of incident light, I is intensity of emergent light, E is extinction, c = molar concentration, d = thickness in cm.) In this work El, refers to log IO/I at a wavelength maximum, using a solution containing 1 % of vitamincontaining substance and a 1 cm. cell.

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