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640-03-9

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Preparation and (E/Z)-Isomerization of the Diastereoisomers of Violaxanthin
Violaxanthin A (=(all-E,3S,5S,6R,3′S,5′S,6′ R)-5,6:5′,6′-diepoxy-5,6,5′,6′-tetrahydro-β, β-carotene-3,3′-diol = syn,syn-violaxanthin; 5) and violaxanthin B (=(all-E,3S,5S,6R,3′S,5′R,6′S)-5,6:5′, 6′-diepoxy-5,6,5′,6′-tetrahydro-β,β-carotene-3, 3′-diol = syn,anti-violaxanthin; 6) were prepared by epoxidation of zeaxanthin diacetate (1) with monoperphthalic acid. Violaxanthins 5 and 6 were submitted to thermal isomerization and I2-catalyzed photoisomerization. The structure of the main products, i.e., (9Z)-5, (13Z)-5, (9Z)-6, (9′Z)-6, (13Z)-6, and (13′Z)-6, was determined by their UV/VIS, CD, 1H-NMR, 13C-NMR, and mass spectra.
Molnar, Peter,Deli, Jozsef,Zsila, Ferenc,Steck, Andrea,Pfander, Hanspeter,Toth, Gyula
p. 11 - 27
(2007/10/03)

PREPARATION OF MONO-CIS ANTHERAXANTHINS AND DETERMINATION OF THEIR GEOMETRICAL CONFIGURATION BY (13)C-NMR SPECTRAL ANALYSIS
Using (13)C-NMR methods, the stereochemistry of eight mono-cis carotenoids obtained by stereomutation of natural (3S, 5R, 6S, 3'R)- and semisynthetic (3S, 5S, 6R, 3'R)-all-trans-antheraxanthins has been established.The carbon-13 data support our earlier p
Molnar, P.,Radics, L.,Szabolcs, J.
p. 477 - 486
(2007/10/02)

Absolute configuration of antheraxanthin, 'cis-antheraxanthin' and of the stereoisomeric mutatoxanthins
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Marki Fischer,Buchecker,Eugster,et al.
p. 2198 - 2211
(2007/10/02)

Optical rotatory dispersion of carotenoids.
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Bartlett,Klyne,Mose,Scopes,Galasko,Mallams,Weedon,Szabolcs,Toth
p. 2527 - 2544
(2007/10/07)

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Chemical Properties

Melting Point: 170-171 °C(Solv: benzene (71-43-2); hexane (110-54-3))
Boiling Point: 708.6°C at 760 mmHg
Flash Point:382.4°C
Density: 1.055g/cm³
Vapor Pressure: 3.32E-23mmHg at 25°C
PKA: 14.86±0.70(Predicted)
PSA: 52.99000
LogP: 9.75860

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