ZIB

1

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Präbetanin, ein Schwefelsäure-halbester des Betanins. Ein Beitrag zur Kenntnis der Betacyane (1967)

Wyler, H. ; Rösler, H. ; Mercier, M. ; [et al.]

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 50 (1967), S. 545-561

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Prebetanin, a minor companion of betanin in the red beet, was isolated and found to be the 6′-sulfuric acid half-ester of betanin. The arguments are based on elemental analyses, partial hydrolysis and methanolysis, and on comparison of the NMR-spectra of prebetanin and betanin, and of their derivatives.

Additional Material: 3 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19670500220

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2

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L'aromatisation acido-catalysée de l'oxime d'une cyclohexadiénone (1965)

Dvolaitzky, Maya ; Dreiding, André S.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 48 (1965), S. 1988-1998

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: p-Cyclohexadienone-oximes show NMR.-signals for the syn-α-proton at about δ = 6,9; the syn-β-, the anti-α-and the anti-β-proton signals, however, appear in the region of δ = 6,0-6,4. This is based on a comparison of the NMR.-spectra of the oximes of spiro[5 · 5]undeca-1,4-diene-3-one and 4-bromo-spiro[5 · 5]undeca-1,4-diene-3-one and on IR.-spectroscopic data and steric considerations. These chemical shifts differ characteristically from those of the corresponding vinyl hydrogens of the parent p-cyclohexadienones; the difference must be attributed on the one hand to the effect of the syn-hydroxyl group and on the other to the nitrogen. On this basis it is possible to assign syn- and anti-configurations respectively to the oximes of steroidal A-ring dienones and even to determine quantitatively the composition of mixtures of the syn-anti isomers, which are usually difficult to separate.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19650480820

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Synthese von Trispiro[5.2.2.5.2.2.]heneicosa-1,4,13,16-tetraen-3,15-dion durch doppelte intramolekulare C-Alkylierung eines Diphenols (1967)

Atkinson, R. S. ; Dreiding, André S.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 50 (1967), S. 23-34

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: A complex trispiro-bisdienone has been made available through a relatively simple series of reactions.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19670500106

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4

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Derivate der Betalaminsäure (1965)

Wilcox, M. E. ; Wyler, H. ; Dreiding, André S.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 48 (1965), S. 1922-1927

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Betalamic acid, the structural unit which is characteristic for the watersoluble centrospermae pigments, the betacyanins and the betaxanthins, has been prepared as the semicarbazone of the dimethyl ester by a “base exchange reaction” from betanidin trimethyl ester and semicarbazide. The UV.- and NMR.-spectra support the proposed structure. The semicarbazone has been reconverted to betanidin trimethyl ester by means of cyclodopa methyl ester.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19650480810

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5

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Umsetzungen des Cyclohex-3-en-carbaldehyd-p-toluolsulfonylhydrazonsEin Teil dieser Resultate wurde am 1964-Symposium «Modern Aspects of Stereochemistry» in Sheffield, England, vorgetragen [1]. (1968)

Rey, M. ; Begrich, R. ; Kirmse, W. ; [et al.]

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 51 (1968), S. 1001-1010

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The vacuum thermolysis (80-90°) of the sodium salt of cyclohex-3-ene-carbaldehyde p-toluenesulfonylhydrazone (1) in silicone oil gave diazomethyl-cyclohex-3-ene (2). Pyrolytic and photolytic decomposition of this diazo compound 2 lead to methylenecyclohex-3-ene (5) and bicyclo [4.1.0]hept-2-ene (6) (about 3:1), while the CuCl catalyzed cleavage yielded only 5. The postulated carbene mechanism should also apply under the direct aprotic decomposition conditions of the sodium salt of 1 in diglyme, where methylenecyclohex-3-ene and bicyclo[4.1.0]hept-2-ene (about 3:1) were formed besides small amounts of 1-methylcyclohexa-1, 3-diene (9) and bicyclo [4.1.0]hept-3-ene (8). Under protic conditions (in ethylene-glycol) methylenecyclohex-3-ene, 1-methylcyclohexa-1, 3-diene and 1-methylcyclohexa-1, 4-diene (14) were produced in a ratio of 1:1:1.The direct mild thermolysis of cyclohex-3-ene-carbaldehyde p-toluenesulfonylhydrazone (1) in benzene solution afforded N-(p-toluenesulfinyl)-O-(p-toluenesulfinyl)-cyclohex-3-en-yl-α-methanolamine (15) and di-(cyclohex-3-en-yl-methyl)-ammonium p-toluenesulfonate (16), the structures of which were supported by their nmr. spectra and by alkaline cleavage.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19680510502

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6

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Biogenese der Betalaine Biotransformation von Dopa und Tyrosin in den Betalaminsäureteil des Betanins. Vorläufige MitteilungEine ausführliche Mitteilung ist in Vorbereitung. (1968)

Miller, H. E. ; Rösler, H. ; Wohlpart, A. ; [et al.]

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 51 (1968), S. 1470-1474

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: During studies on the biogenesis of betalains (I) in cactus fruits (Opuntia sp.). DL-dopa-1-[14C] and -2-[14C] were incorporated into betanin (III) which was obtained radiopure after crystallization. The specific activity remained constant after conversion to betanidin (IV) and to a neobetanidin derivative (IX). Reaction of radiobetanin with proline afforded indicaxanthin (V) carrying more than 90% of the radioactivity. Dopa (VI) is thus an efficient precursor for betalamic acid (VIII) but not for cyclodopa (VII). Decarboxylation of radiobetanidin and radioindicaxanthin showed that the carboxyl group of dopa remained a carboxyl group in the biotransformation to betalamic acid. It is concluded that the aromatic ring of dopa is cleaved and that re-cyclization involving the nitrogen generates the dihydropyridine moiety. Under the same conditions mevalonic acid, aspartic acid and phenylalanine showed low incorporations. Studies with beet seedlings and DL-dopa-1-[14C], -2-[14C] and DL-tyrosine-1-[14C] afforded similar results but with low incorporations.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19680510634

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7

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Stereochemie von Betanidin und Isobetanidin.Von A.S.D. im Rahmen von 2 Vorträgen an der Universität Göttingen und am «Symposium on Recent Advances of Plant Phenolics» in New Delhi am 24. 9. bzw. am 5. 10. 64 bekanntgegeben. 8. Mitteilung.7. Mitteilung siehe [14]. Zur Konstitution des Randenfarbstoffes Betanin (1965)

Wilcox, M. E. ; Wyler, H. ; Dreiding, André S.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 48 (1965), S. 1134-1147

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The base exchange of betanidin and isobetanidin with 5,6-dihydroxy-2,3-dihydroindole-2R-carboxylic acid (named R-Cyclodopa, III) led to the formation of enantio-isobetanidin and enantio-betanidin, respectively. The enantiomers exhibited rotatory dispersion curves which were the mirror images of those of betanidin and isobetanidin. Thus it is shown that, in agreement with our proposed structure for betanidin, there exists in the molecule another, and only one other, asymmetric centre in addition to that present at C2, and furthermore, that isobetanidin differs from betanidin only in its configuration at this second centre (C15).

Additional Material: 5 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19650480519

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8

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Reaktion von α-Chlorpropionyl-chlorid mit Triäthylamin Bildung eines Säurechlorid-enolesters (1968)

Giger, R. ; Rey, M. ; Dreiding, André S.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 51 (1968), S. 1466-1469

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Previous and new data are interpreted to mean that the two isomeric products C6H7Cl3O2 obtained by the selfcondensation of α-chloropropionyl chloride (I) in the presence of about 0.5 moleequivalent triethyl amine are acid chloride enolesters, namely cis- and trans-1. 2-dichloropropenyl-α-chloropropionate (VIII). Similarly, dichloroacetyl chloride (X) was converted to trichlorovinyl-dichloroacetate (XI).

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19680510633

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Die Struktur des BetaninsDie Ergebnisse dieser Arbeit wurden im Rahmen von zwei Vorträgen (A.S.D.) an der Universität Göttingen und am «Symposium on Recent Advances of Plant Phenolics» in New Delhi am 24. September und 5. Oktober 1964 bekannt gegeben.. 7. Mitteilung6. Mitteilung siehe [1].. Über die Konstitution des Randenfarbstoffes Betanin (1965)

Wilcox, M. E. ; Wyler, H. ; Mabry, T. J. ; [et al.]

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 48 (1965), S. 252-258

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: It is shown that the glucose residue in betanin is attached at the 5-hydroxyl group (structure 2): Treatment of betanin with diazomethane, acidic hydrolysis and acetylation afforded 5-O-acetyl-6-O-methyl-neobetanidin trimethylester (9), which was cleaved by alkali. The cleavage product was esterified with methanol and oxydized by means of FRÉMY salt to 5-hydroxy-6-methoxy-2-methoxycarbonyl-indole (15).

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19650480125

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10

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Umwandlung eines Betacyans in ein Betaxanthin Synthese von Indicaxanthin aus BetaninVon A.S.D. im Rahmen von 2 Vorträgen an der Universität Göttingen und am «Symposium on Recent Advances of Plant Phenolics» in New Delhi am 24. 9. und 5. 10. 64 bekannt gegeben. (1965)

Wyler, H. ; Wilcox, M. E. ; Dreiding, André S.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 48 (1965), S. 361-366

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: When betanin (III) was treated with S-proline (IV), a base exchange took place which produced indicaxanthin (I). In this way this yellow pigment of the cactus fruit was partially synthesized by a method which should be generally applicable for the mutual interconversion of betacyanins and betaxanthins. For it was also possible to transform indicaxanthin into betanidin (II) by a base exchange with 5,6-dihydroxy-2,3-dihydroindole-2S-carboxylic acid (V).

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19650480214

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