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CAS Number : 116-30-3
Chemical formula: C40H50O2
Molar mass: 562.82 g/mol
Rhodoxanthin is a xanthophyll pigment with a purple color that is found in small quantities in a variety of plants including Taxus baccata and Lonicera morrowii.
Rhodoxanthin is also found in the feathers of some birds.
As a food additive it is used under the E number E161f as a food coloring.
Rhodoxanthin is not approved for use in the EU or US; however, it is approved in Australia and New Zealand
Rhodoxanthin The major red carotenoids in autumnal, colored leaves were analyzed in seven species and one variety that belong to two families of gymnosperms.
Rhodoxanthin The red carotenoids in leaves of all species and variety were rhodoxanthin, which was separated into three geometric isomers, (6Z, 6′Z)-rhodoxanthin, (6Z)-rhodoxanthin and (all E)-rhodoxanthin.
Rhodoxanthin The effects of daylight intensity on the content and composition of the leaf pigments of autumnal coloration were studied with leaves ofCryptomeria japonica (evergreen) and Taxodium distichum (deciduous) grown under different grades of shade.
Rhodoxanthin Histological observation showed that many reddish particles of rhodoxanthin were observed inside chromoplasts on the sunny side of a leaf at the early stage of coloration and that the content of the reddish particles was decreased toward the shady side from the sunny side of a leaf.
Rhodoxanthin The transition from chloroplasts to chromoplasts was observed and cells at different stage of coloration independently existed in the mesophyll tissue of a leaf.
The content of rhodoxanthin became maximum when the daylight intensity was 4.1–7.4 MJ m−2 day−1 and the daily mean temp.
Rhodoxanthin was below 8.1 C inCryptomeria, and 3.1–8.3 MJ m−2 day−1 and 13.4 C inTaxodium.
Rhodoxanthin A red carotenoid pigment was isolated by paper chromatography from extracts of leaves of red pigmented Agathis australis seedlings.
Rhodoxanthin position and shape of the absorption spectra of this pigment in three solvents was identical with those for rhodoxanthin isolated from the arils of Taxus baccata fruit.
Rhodoxanthin behaviour of the red pigment on partitioning between petroleum ether and 90 per cent. methanol, its position on sucrose, celite, and magnesium oxide columns and its solubility in various solvents was consistent with this conclusion.
Rhodoxanthin red leaf pigment and Rhodoxanthin could not be separated when co-chromatographed in two solvent systems.
Rhodoxanthin concentration of this pigment in red seedlings was c.
25 times greater than that in green seedlings while the chlorophyll content in the former was half that of the latter.
Rhodoxanthin implications of these findings are discussed.
Rhodoxanthin hitherto scarcely investigated retro-carotenoid rhodoxanthin possesses high potential for coloration in the food and beverage industry using technofunctional formulations prepared thereof.
Hence, we studied -isomerization pathways of rhodoxanthin, including seven -isomers comprising -configured double bonds at unusual exocyclic and inner polyene chain positions.
Rhodoxanthin mathematical approach was developed to deduce kinetic and thermodynamic parameters of six parallel equilibrium reactions interconnecting -rhodoxanthin with mono-, di-, and tri-(Z)-isomers using multiresponse modeling.
At 40–70 °C in ethyl acetate, reaction rate constants regarding the rotation from - to -rhodoxanthin were 11–14 times higher than those of the common -isomerization reaction at C-13,14 of the non-retro-structured carotenoid canthaxanthin.
Moreover, Rhodoxanthin the equilibrium reaction between - and -rhodoxanthin was strongly product favored as indicated by negative Gibbs energies, which is unusual for carotenoids within the studied temperatures.
Rhodoxanthin Overall, this study provides novel insights into structure-related dependencies of -isomerization reaction kinetics and thermodynamics of polyenes.
Rhodoxanthin Lleaves, strong sunlight or its combination with drought induces the accumulation of the red keto-carotenoid, Rhodoxanthin.
Rhodoxanthin Simultaneously, the transformation of chloroplasts into chromoplasts accompanied by degradation of thylakoid membranes and formation of plastoglobuli, large in size and number, takes place.
Rhodoxanthin Depending on stress conditions the build up of rhodoxantin occurred along with the loss of chlorophyll or on the background of relatively high content of the pigment in the leaves.
Rhodoxanthin Microspectrophotometrical measurements showed the presence of chlorophyll-free plastids and retention of carotenoids during leaf adaptation to strong sunlight.
Rhodoxanthin The plastid spectra contained absorption bands of common for higher plants carotenoids together with those of rhodoxantin, with absorption maxima situated in the blue (440–480 nm) and the green ranges of the spectrum, respectively.
Rhodoxanthin studies of whole-leaf optical properties revealed a broad band of rhodoxanthin absorption in the blue–green range peaking near 540–550 nm.
Within this spectral band the accumulation of rhodoxanthin occurring, probably, in plastoglobuli considerably increased light absorption by stressed Aloe leaves.
Rhodoxanthin possible photoprotective function of rhodoxanthin and other carotenoids as an internal light trap analogous to that accomplished by anthocyanins in other plant species is discussed.
Rhodoxanthin is a brilliant red pigment that is widely but sporadically represented in nature.
Rhodoxanthin is a member of an atypical family of carotenoids that contain a register shift in the alternating pattern of double and single bonds relative to that of the more widely occurring carotenoids and are therefore referred to as retro-carotenoids.
Rhodoxanthin In retro-carotenoids, the rings are more planar relative to the polyene backbone, resulting in increased conjugation that changes the vibrational modes of the molecule, resulting in altered vibrational spectra relative to other carotenoids.
Rhodoxanthin has been observed in the sun-stressed leaves of a number of conifers as well as in similarly stressed leaves of angiosperms in the genus Aloe.
Rhodoxanthin feathers of a small number of bird species accumulate rhodoxanthin, in some cases, due to conversion of consumed zeaxanthin or lutein precursors and, in other cases, due to the dietary consumption of rhodoxanthin-containing plants.
Rhodoxanthin accumulates notably and at high levels in the arils of yew and in the berries of certain species of honeysuckle.
The pathways and enzymes leading to the major plant carotenoids are well defined and are the subject of several excellent reviews, e.g.,
Lycopene, the first colored compound in the carotenoid pathway, is modified by distinct cyclases to produce either β-carotene or α-carotene.
Rhodoxanthin while the biosynthetic routes to the major plant carotenoids are well established, the enzymes and pathway(s) to retro-carotenoids have remained elusive.
In the absence of enzymatic or genetic investigations, proposed routes have been based on chemical composition analyses of carotenoid-containing material.
Rhodoxanthin Some gymnosperms, including Cryptomeria japonica, exhibit needle reddening caused by red xanthophyll pigment, rhodoxanthin accumulation during long-term cold acclimation.
Although photoprotective role of rhodoxanthin, serves as a “sunscreen”, was proposed, the key environmental and/or physiological factors involved in rhodoxanthin accumulation remain unclear.
Light intensity related to the maximum value of rhodoxanthin on chlorophyll (Chl) basis, but not to that on FW basis, because Chl content decreased with increasing light intensity.
The relationship between the rhodoxanthin content and the seasonal growth temperature was different among light treatments, reflecting differences in the amount of excess light among light treatments Furthermore, the rhodoxanthin content correlated significantly with the Fv/Fm, nocturnal DPS and β-carotene level in winter.
Rhodoxanthin, which is found in nature in the berries of evergreen trees such as Paxus Baccatajs widely used as a coloring material for foodstuffs and beverages as well as pharmaceutical and cosmetic preparations.
Rhodoxanthin imparts to foodstuffs, pharmaceutical and cosmetic preparations a red coloration.
In the past rhodoxanthin has been produced by isolating this material from its natural source such as from the berries of evergreen plants. This procedure has proven extremely disadvantageous due to the fact that rhodoxanthin occurs only in small amounts in these berries.
Therefore, a great quantity of these berries must be utilized in order to isolate a small amount of rhodoxanthin.
Additionally, the process whereby rhodoxanthin is isolated from the berries of green plants has proven extremely cumbersome and uneconomical.
Up until the present time there has been no procedure for directly chemically synthesizing rhodoxanthin without isolating rhodoxanthin or precursors of rhodoxanthin from their natural source.
Therefore, it has been long desired in the art to provide a method for chemically synthesizing rhodoxanthin so as to eliminate the necessity of isolating rhodoxanthin or its precursors from its natural source.
In the winter, western redcedar produces and accumulates a carotenoid pigment called Rhodoxanthin, which changes the color of the leaves from green to reddish-brown.
Rhodoxanthin plants photosynthesize, they are using light energy to make glucose and oxygen from carbon dioxide and water.
Rhodoxanthin main factors affecting the rate of photosynthesis are carbon dioxide, light intensity, and optimum temperatures.
Rhodoxanthin one of these factors can become a limiting factor during the process.
In winter, cold temperatures are often the limiting factor.
Low temperatures cause the enzymes responsible for photosynthesis to have little energy, resulting in a slow rate of photosynthesis and excess light energy.
Excess light energy is hazardous; it has the potential to destroy the photosynthetic apparatus and lead to cell death.
Rhodoxanthin is a xanthophyll carotenoid that absorbs photons in the blue and green ranges of the spectrum.
So while rhodoxanthin is absorbing photons in the range of light between ~440-550 nm, it is reflecting colors above and below these wavelengths, lending to the reddish-brown coloration you see in western redcedar in the winter.
Douglas-fir uses the xanthophyll pigments zeaxanthin and antheraxanthin to absorb photons in the blue region of the light spectrum (400-500 nm), lending to the yellowish coloration that is produced.
This is because blue and red light fall into the most effective wavelength ranges for photosynthesis, therefore these colors are absorbed while green light is reflected.
Basically, in western redcedar, rhodoxanthin is acting as a sunscreen at low temperatures.
When temperatures are low, the rate of photosynthesis decreases, which results in unused light that must be absorbed to prevent damage to the photosynthetic apparatus.
Rhodoxanthin is absorbing this excess light, thereby decreasing the light intensity reaching the photosynthetic apparatus and protecting it from damage.
Because rhodoxanthin is absorbing light between 440-550 nm, wavelengths above and below this range are reflected, thereby causing western redcedar leaves to take on a reddish-brown hue.
Interestingly, rhodoxanthin accumulation in western redcedar is thought to only be produced and accumulated in young redcedar, not in older trees, and only in the sun leaves, not the shaded leaves.
Rhodoxanthin is unknown if and how rhodoxanthin production is lost as a redcedar ages.
Rhodoxanthin is a xanthophyll pigment with a purple color that is found in small quantities in a variety plants including Taxus baccata. Rhodoxanthin is also found in the feathers of some birds.
Rhodoxanthin As a food additive it is used under the E number E161f as a food coloring.
Taxus baccata is a conifer native to western, central and southern Europe, northwest Africa, northern Iran and southwest Asia.
Rhodoxanthin is the tree originally known as yew, though with other related trees becoming known, it may be now known as the common yew, or European yew.
Rhodoxanthin comprised ∼5% of carotenoids in many oriole feathers, and up to 18% in the reddest one.
Redness in oriole feathers with rhodoxanthin correlated with amounts of that pigment, rather than with amounts of red 4-keto-carotenoids like canthaxanthin normally present in orange oriole feathers.
Redness in feathers with rhodoxanthin also tended to be greatest in feathers with the least amounts of carotenoids.
The anomalous rhodoxanthin altered the normal relationship between redness and 4-keto-carotenoid concentration, and total feather carotenoid concentration in Baltimore Orioles.
We confirm the presence of rhodoxanthin in the berries of Tatarian honeysuckle (L. tatarica).
Rhodoxanthin produces a shoulder at ∼520 nm of the reflectance spectrum of feathers in which it occurs.
Names
IUPAC name
(4E)-3,5,5-Trimethyl-4-[(2E,4E,6E,8E,10E,12E,14E,16E,18E)-3,7,12,16-Tetramethyl-18-(2,6,6-trimethyl-4-oxo-1-cyclohex-2-enylidene)octadeca-2,4,6,8,10,12,14,16-octaenylidene]-1-cyclohex-2-enone
Other names
•4',5'-Didehydro-retro-β-carotene-3,3'-dione
•E161f
Identifiers
CAS Number : 116-30-3
ChemSpider :4444663
E number : E161f (colours)
KEGG :C08610
PubChem CID :5281251
UNII :51V984ID9Q
Properties
Chemical formula: C40H50O2
Molar mass: 562.82 g/mol
Appearance: Purple crystals
Melting point: 219 °C (426 °F; 492 K)
Synonyms
Rhodoxanthin
116-30-3
UNII-51V984ID9Q
51V984ID9Q
SCHEMBL42598
CHEBI:8835
DTXSID201017050
LMPR01070280
(4E)-3,5,5-trimethyl-4-[(2E,4E,6E,8E,10E,12E,14E,16E,18E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-ylidene)octadeca-2,4,6,8,10,12,14,16-octaenylidene]cyclohex-2-en-1-one
C08610
Q2479965
4,5'-retro-beta,beta-Carotene-3,3'-dione, 4',5'-didehydro-
