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20-September-2008 09:29:08 - Zeaxanthin Zeaxanthin Zeaxanthin IUPAC name 4-18-4-hydroxy-2,6,6-trimethyl -1-cyclohexenyl- 3,7,12,16-tetramethyl-octadeca- 1,3,5,7,9,11,13,15,17-nonaenyl- 3,5,5-trimethyl-cyclohex-3-en-1-ol Other names zeaxanthin; β,β-carotene-3,3'-diol Identifiers CAS number 144-68-3 Properties Molecular formula C40H56O2 Molar mass 568.88 g/mol Appearance orange-red Melting point 215.5 °C 488.7 K Solubility in water insol. Related compounds Related compounds lutein xanthophyll Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Zeaxanthin is one of the two carotenoids contained within the retina of the eye. Within the central macula, zeaxanthin is the dominant component, whereas in the peripheral retina, lutein predominates. Lutein and zeaxanthin have identical chemical formulas and are isomers, but they are not stereoisomers. The main difference between them is in the location of a double bond in one of the end rings. This difference gives lutein three chiral centers whereas zeaxanthin has two. As a food additive, zeaxanthin is a food dye with E number E161h. Contents 1 Isomers 2 Relationship with diseases of the eye 3 Natural occurrence 4 External links 5 References Isomers Because of symmetry, the 3R,3'S and 3S,3'R stereoisomers of zeaxanthin are identical. Therefore, zeaxanthin has only three stereoisomeric forms. The 3R,3'S stereoisomer is called meso-zeaxanthin. The principal natural form of zeaxanthin is 3R,3'R-zeaxanthin. The macula mainly contains the 3R,3'R- and meso-zeaxanthin forms, but it also contains much smaller amounts of the third 3S,3'S form. Relationship with diseases of the eye There is epidemiological evidence of a relationship between low plasma concentrations of lutein and zeaxanthin on the one hand, and the risk of developing age-related macular degeneration AMD on the other. Some studies support the view that supplemental lutein and/or zeaxanthin help protect against AMD. There is also epidemiological evidence that increasing lutein and zeaxanthin intake lowers the risk of cataract development.citation needed On September 10, 2007, in a 6-year study, researchers, led by John Paul SanGiovanni of the National Eye Institute, Maryland found that Lutein and zeaxanthin nutrients in eggs, spinach and other green vegetables protect against blindness macular degeneration, affecting 1.2 million Americans, mostly after age 65. Lutein and zeaxanthin reduce the risk of AMD journal Archives of Ophthalmology. Foods considered good sources of the nutrients also include kale, turnip greens, collard greens, romaine lettuce, broccoli, zucchini, corn, garden peas and Brussels sprouts.1 Natural occurrence Zeaxanthin is one of the most common carotenoid alcohols found in nature. It is the pigment that gives corn, saffron, and many other plants their characteristic color. Zeaxanthin breaks down to form picrocrocin and safranal, which are responsible for the taste and aroma of saffron. External links BioCyc References ^ Age-Related Eye Disease Study Research Group, SanGiovanni JP, Chew EY, et al. The relationship of dietary carotenoid and vitamin A, E, and C intake with age-related macular degeneration in a case-control study: AREDS Report No. 22. 2007 Arch Ophthalmol 125:1225-1232. PMID 17846363. v d e Carotenoids Carotenes: Carotene Alpha-carotene · Beta-carotene · Lycopene · Phytoene Phytofluene · Neurosporene Retinoids: Acitretin · Alitretinoin · Apocarotenal · Bexarotene · Etretinate · Fenretinide · Isotretinoin · Retinaldehyde · Tazarotene · Vitamin A Retinol, Tretinoin Xanthophylls: Antheraxanthin · Astaxanthin · Canthaxanthin · Citranaxanthin · Cryptoxanthin · Diadinoxanthin · Diatoxanthin · Dinoxanthin · Flavoxanthin · Fucoxanthin · Lutein · Neoxanthin · Rhodoxanthin · Rubixanthin · Violaxanthin · Zeaxanthin Other: Crocin · Crocetin · Peridinin · Food orange 7 Retrieved from http://en..org/wiki/Zeaxanthin Categories: Food colorings | CarotenoidsHidden categories: All articles with statements | Articles with statements since May 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages БългарÑ?ки Deutsch Español Français Italiano Nederlands Polski Português Türkçe This page was last modified on 16 June 2008, at 04:5
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