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Zeaxanthin information


Zeaxanthin
Structural formula of zeaxanthin
Space-filling model of the zeaxanthin molecule
Names
IUPAC name
(3R,3′R)-β,β-Carotene-3,3′-diol
Systematic IUPAC name
(1R,1′R)-4,4′-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(3,5,5-trimethylcyclohex-3-en-1-ol)
Identifiers
CAS Number
  • 144-68-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:27547 checkY
ChemSpider
  • 4444421 checkY
ECHA InfoCard 100.005.125 Edit this at Wikidata
E number E161h (colours)
PubChem CID
  • 5280899
UNII
  • CV0IB81ORO checkY
CompTox Dashboard (EPA)
  • DTXSID5046807 Edit this at Wikidata
InChI
  • InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1 checkY
    Key: JKQXZKUSFCKOGQ-QAYBQHTQSA-N checkY
  • InChI=1/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1
    Key: JKQXZKUSFCKOGQ-QAYBQHTQBL
SMILES
  • CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C[C@H](CC2(C)C)O)C)\C)\C)/C)/C
Properties
Chemical formula
C40H56O2
Molar mass 568.88 g/mol
Appearance orange-red
Melting point 215.5 °C (419.9 °F; 488.6 K)
Solubility in water
insol.
Related compounds
Related compounds
lutein
xanthophyll
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Zeaxanthin is one of the most common carotenoids in nature, and is used in the xanthophyll cycle. Synthesized in plants and some micro-organisms, it is the pigment that gives paprika (made from bell peppers), corn, saffron, goji (wolfberries), and many other plants and microbes their characteristic color.[1][2]

The name (pronounced zee-uh-zan'-thin) is derived from Zea mays (common yellow maize corn, in which zeaxanthin provides the primary yellow pigment), plus xanthos, the Greek word for "yellow" (see xanthophyll).

Xanthophylls such as zeaxanthin are found in highest quantity in the leaves of most green plants, where they act to modulate light energy and perhaps serve as a non-photochemical quenching agent to deal with triplet chlorophyll (an excited form of chlorophyll) which is overproduced at high light levels during photosynthesis.[3] Zeaxanthin in guard cells acts as a blue light photoreceptor which mediates the stomatal opening.[4]

Animals derive zeaxanthin from a plant diet.[2] Zeaxanthin is one of the two primary xanthophyll carotenoids contained within the retina of the eye. Zeaxanthin supplements are typically taken on the supposition of supporting eye health. Although there are no reported side effects from taking zeaxanthin supplements, the actual health effects of zeaxanthin and lutein are not proven,[5][6][7] and, as of 2018, there is no regulatory approval in the European Union or the United States for health claims about products that contain zeaxanthin.

As a food additive, zeaxanthin is a food dye with E number E161h.

  1. ^ Encyclopedia.com. "Carotenoids". Retrieved 6 May 2012.
  2. ^ a b "Lutein + Zeaxanthin Content of Selected Foods". Linus Pauling Institute, Oregon State University, Corvallis. 2014. Retrieved 20 May 2014.
  3. ^ Bassi, Roberto; Dall'Osto, Luca (2021). "Dissipation of Light Energy Absorbed in Excess: The Molecular Mechanisms". Annual Review of Plant Biology. 72: 47–76. doi:10.1146/annurev-arplant-071720-015522. PMID 34143647. S2CID 235480018.
  4. ^ Kochhar, S. L.; Gujral, Sukhbir Kaur (2020). "Transpiration". Plant Physiology: Theory and Applications (2 ed.). Cambridge University Press. pp. 75–99. doi:10.1017/9781108486392.006. ISBN 978-1-108-48639-2.
  5. ^ Age-Related Eye Disease Study 2 Research Group (2013). "Lutein + zeaxanthin and omega-3 fatty acids for age-related macular degeneration: The Age-Related Eye Disease Study 2 (AREDS2) randomized clinical trial". JAMA. 309 (19): 2005–15. doi:10.1001/jama.2013.4997. PMID 23644932.{{cite journal}}: CS1 maint: numeric names: authors list (link)
  6. ^ Pinazo-Durán, M. D.; Gómez-Ulla, F; Arias, L; et al. (2014). "Do Nutritional Supplements Have a Role in Age Macular Degeneration Prevention?". Journal of Ophthalmology. 2014: 1–15. doi:10.1155/2014/901686. PMC 3941929. PMID 24672708.
  7. ^ Koo, E; Neuringer, M; Sangiovanni, J. P. (2014). "Macular xanthophylls, lipoprotein-related genes, and age-related macular degeneration". American Journal of Clinical Nutrition. 100 (Supplement 1): 336S–346S. doi:10.3945/ajcn.113.071563. PMC 4144106. PMID 24829491.

and 26 Related for: Zeaxanthin information

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Zeaxanthin

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Zeaxanthin is one of the most common carotenoids in nature, and is used in the xanthophyll cycle. Synthesized in plants and some micro-organisms, it is...

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Lutein

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animal fats. Lutein is isomeric with zeaxanthin, differing only in the placement of one double bond. Lutein and zeaxanthin can be interconverted in the body...

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Xanthophyll

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violaxanthin, antheraxanthin, and zeaxanthin. During light stress, violaxanthin is converted, i.e. reduced, to zeaxanthin via the intermediate antheraxanthin...

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Zeaxanthin epoxidase

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Zeaxanthin epoxidase (EC 1.14.13.90, Zea-epoxidase) is an enzyme with systematic name zeaxanthin,NAD(P)H:oxygen oxidoreductase. This enzyme catalyses the...

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Zeaxanthin glucosyltransferase

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Zeaxanthin glucosyltransferase (EC 2.4.1.276, crtX (gene)) is an enzyme with systematic name UDP-glucose:zeaxanthin beta-D-glucosyltransferase. This enzyme...

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Violaxanthin

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variety of plants. Violaxanthin is the product of the epoxidation of zeaxanthin where the oxygen atoms are from reactive oxygen species (ROS). Such ROS's...

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Macula

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from its content of lutein and zeaxanthin, which are yellow xanthophyll carotenoids, derived from the diet. Zeaxanthin predominates at the macula, while...

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Human eye

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lutein and zeaxanthin within the macula may be associated with an increase in the risk of age-related macular degeneration. Lutein and zeaxanthin act as antioxidants...

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Paprika

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zeaxanthin, lutein and β-cryptoxanthin, whereas red colors derive from capsanthin and capsorubin. One study found high concentrations of zeaxanthin in...

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Limonene

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Gamma-Carotene Delta-Carotene Lycopene Neurosporene Phytofluene Phytoene Xanthophylls: Canthaxanthin Cryptoxanthin Zeaxanthin Astaxanthin Lutein Rubixanthin...

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Carotenoid isomerooxygenase

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name zeaxanthin:oxygen 15,15'-oxidoreductase (bond-cleaving, cis-isomerizing). This enzyme catalyses the following chemical reaction zeaxanthin + O2 ⇌...

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Photophobia

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Journal of Food Science, reviews studies of effects of consuming Lutein and Zeaxanthin on visual performance, and notes a decrease in sensitivity to glare. Photophobia...

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Flint corn

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Linnaeus variant of maize, any kernel may contain the yellow pigment zeaxanthin but at more varying concentrations. Regional varieties with specific coloration...

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Astaxanthin

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compounds known as carotenones or terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups...

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Carotenoid

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that they can be converted to retinol). In the eye, lutein, meso-zeaxanthin, and zeaxanthin are present as macular pigments whose importance in visual function...

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Fovea centralis

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has a high concentration of the yellow carotenoid pigments lutein and zeaxanthin. They are concentrated in the Henle fiber layer (photoreceptor axons that...

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Urtica dioica

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carotenoid contents, especially lutein, β-carotene and zeaxanthin, of which lutein and zeaxanthin act as yellow pigments. Feeding as little as 6.25 g dry...

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Yogurt

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Protein 9.0 g Vitamins Quantity %DV† Vitamin A equiv. beta-Carotene lutein zeaxanthin 0% 26 μg 22 μg Thiamine (B1) 2% 0.023 mg Riboflavin (B2) 21% 0.278 mg...

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Guacamole

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beta-sitosterol. They also contain carotenoids, such as beta-carotene, zeaxanthin and lutein. Mantequilla de pobre (Spanish for 'poor-man's butter') is...

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Apple

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Protein 0.26 g Vitamins Quantity %DV† Vitamin A equiv. beta-Carotene lutein zeaxanthin 0% 3 μg 0% 27 μg 29 μg Thiamine (B1) 1% 0.017 mg Riboflavin (B2) 2% 0...

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Hazelnut

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14.95 g Vitamins Quantity %DV† Vitamin A equiv. beta-Carotene lutein zeaxanthin 0% 1 μg 0% 11 μg 92 μg Thiamine (B1) 54% 0.643 mg Riboflavin (B2) 9% 0...

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Xerophyte

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excess energy as heat through the xanthophyll cycle. Violaxanthin and zeaxanthin are carotenoid molecules within the chloroplasts called xanthophylls....

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Hass avocado

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Hass avocados contain phytosterols and carotenoids, including lutein and zeaxanthin. Avocados have diverse fats. For a typical avocado: About 75% of an avocado's...

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Dormancy

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defective in zeaxanthin epoxidase gene, which are linked to ABA-synthesis pathway. Seeds with higher ABA content, from over-expressing zeaxanthin epoxidase...

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Picrocrocin

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by dehydration. Picrocrocin is a degradation product of the carotenoid zeaxanthin.[citation needed] Caballero-Ortega H, Pereda-Miranda R, Abdullaev FI (2007)...

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C40H56O2

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C40H56O2 (molar mass: 568.87 g/mol) may refer to: Lutein Zeaxanthin Meso-zeaxanthin (3R,3´S-zeaxanthin) This set index page lists chemical structure articles...

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