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{{short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| verifiedrevid = 451108958 | verifiedrevid = 470635696
| Name = Zeaxanthin | Name = Zeaxanthin
| ImageFile =Zeaxanthin2.svg | ImageFile =Zeaxanthin2.svg
| ImageSize = 250px | ImageSize = 320px
| ImageAlt = Structural formula of zeaxanthin
| ImageName = Zeaxanthin
| ImageFile1 = Zeaxanthin molecule spacefill.png
| IUPACName = 4--3,5,5-trimethyl-cyclohex-3-en-1-ol
| ImageSize1 = 320
| OtherNames = β,β-carotene-3,3'-diol
| ImageAlt1 = Space-filling model of the zeaxanthin molecule
| Section1 = {{Chembox Identifiers
| IUPACName = (3''R'',3′''R'')-β,β-Carotene-3,3′-diol
| SystematicName = (1''R'',1′''R'')-4,4′-bis(3,5,5-trimethylcyclohex-3-en-1-ol)
| OtherNames =
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444421 | ChemSpiderID = 4444421
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| RTECS = | RTECS =
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>40</sub>H<sub>56</sub>O<sub>2</sub> | Formula = C<sub>40</sub>H<sub>56</sub>O<sub>2</sub>
| MolarMass = 568.88 g/mol | MolarMass = 568.88 g/mol
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| Viscosity = | Viscosity =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| RPhrases = | HPhrases =
| SPhrases = | PPhrases =
| GHS_ref =
}}
}}
| Section8 = {{Chembox Related
|Section8={{Chembox Related
| OtherAnions = | OtherAnions =
| OtherCations = | OtherCations =
| OtherCpds = ]<br />] | OtherCompounds = ]<br />]
}} }}
}} }}

'''Zeaxanthin''' is one of the most common ]s in nature, and is used in the ]. Synthesized in plants and some micro-organisms, it is the pigment that gives ] (made from bell peppers), ], ], goji (]), and many other plants and microbes their characteristic color.<ref>{{cite web | last=Encyclopedia.com | title=Carotenoids | url=http://www.encyclopedia.com/topic/Carotenoids.aspx| access-date = 6 May 2012}}</ref><ref name="LPI">{{cite web|url=http://lpi.oregonstate.edu/infocenter/phytochemicals/carotenoids/index.html#sources|title=Lutein + Zeaxanthin Content of Selected Foods|publisher=Linus Pauling Institute, Oregon State University, Corvallis|date=2014|access-date=20 May 2014}}</ref>

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

Xanthophylls such as zeaxanthin are found in highest quantity in the ] of most green ], where they act to modulate light energy and perhaps serve as a ] agent to deal with triplet chlorophyll (an excited form of chlorophyll) which is overproduced at high light levels during photosynthesis.<ref>{{cite journal |doi=10.1146/annurev-arplant-071720-015522|title=Dissipation of Light Energy Absorbed in Excess: The Molecular Mechanisms |year=2021 |last1=Bassi |first1=Roberto |last2=Dall'Osto |first2=Luca |journal=Annual Review of Plant Biology |volume=72 |pages=47–76 |pmid=34143647 |s2cid=235480018 |doi-access=free }}</ref> Zeaxanthin in ]s acts as a blue light ] which mediates the ]tal opening.<ref>{{cite book |last1=Kochhar |first1=S. L. |last2=Gujral |first2=Sukhbir Kaur |title=Plant Physiology: Theory and Applications |date=2020 |publisher=Cambridge University Press |isbn=978-1-108-48639-2 |pages=75–99 |edition=2 |doi=10.1017/9781108486392.006 |chapter=Transpiration}}</ref>

Animals derive zeaxanthin from a plant diet.<ref name=LPI/> Zeaxanthin is one of the two primary ] ]s contained within the ] of the ]. 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 ] are not proven,<ref>{{Cite journal|author1=Age-Related Eye Disease Study 2 Research Group|year=2013|title=Lutein + zeaxanthin and omega-3 fatty acids for age-related macular degeneration: The Age-Related Eye Disease Study 2 (AREDS2) randomized clinical trial|journal=JAMA|volume=309|issue=19|pages=2005–15|doi=10.1001/jama.2013.4997|pmid=23644932|doi-access=free}}</ref><ref>{{Cite journal|last1=Pinazo-Durán|first1=M. D.|last2=Gómez-Ulla|first2=F|last3=Arias|first3=L|last4=Araiz|first4=J|last5=Casaroli-Marano|first5=R|last6=Gallego-Pinazo|first6=R|last7=García-Medina|first7=J. J.|last8=López-Gálvez|first8=M. I.|last9=Manzanas|first9=L|display-authors=3|year=2014|title=Do Nutritional Supplements Have a Role in Age Macular Degeneration Prevention?|journal=Journal of Ophthalmology|volume=2014|pages=1–15|doi=10.1155/2014/901686|pmc=3941929|pmid=24672708|last10=Salas|first10=A|last11=Zapata|first11=M|last12=Diaz-Llopis|first12=M|last13=García-Layana|first13=A|doi-access=free}}</ref><ref>{{Cite journal|last1=Koo|first1=E|last2=Neuringer|first2=M|last3=Sangiovanni|first3=J. P.|year=2014|title=Macular xanthophylls, lipoprotein-related genes, and age-related macular degeneration|journal=American Journal of Clinical Nutrition|volume=100|issue=Supplement 1|pages=336S–346S|doi=10.3945/ajcn.113.071563|pmc=4144106|pmid=24829491}}</ref> and, as of 2018, there is no regulatory approval in the ] or the United States for ]s about products that contain zeaxanthin.

As a ], zeaxanthin is a ] with ] E161h.

==Isomers and macular uptake==

] and zeaxanthin have identical chemical formulas and are ]s, but they are not ]s. The only difference between them is in the location of the ] in one of the end rings. This difference gives lutein three ] centers whereas zeaxanthin has two. Because of symmetry, the ] stereoisomers of zeaxanthin are identical. Therefore, zeaxanthin has only three stereoisomeric forms. The (3R,3′S) stereoisomer is called ].

The principal natural form of zeaxanthin is (3R,3′R)-zeaxanthin. The ] mainly contains the (3R,3′R)- and meso-zeaxanthin forms, but it also contains much smaller amounts of the third (3S,3′S) form.<ref>{{Cite journal | pmid = 23703634 | year = 2013 | last1 = Nolan | first1 = J. M. | title = What is meso-zeaxanthin, and where does it come from? | journal = Eye | volume = 27 | issue = 8 | pages = 899–905 | last2 = Meagher | first2 = K | last3 = Kashani | first3 = S | last4 = Beatty | first4 = S | doi = 10.1038/eye.2013.98 | pmc = 3740325 }}</ref> Evidence exists that a specific zeaxanthin-] recruits circulating zeaxanthin and lutein for uptake within the macula.<ref>{{Cite journal | pmid = 20820671 | year = 2010 | last1 = Li | first1 = B | title = Human ocular carotenoid-binding proteins | journal = Photochemical & Photobiological Sciences | volume = 9 | issue = 11 | pages = 1418–25 | last2 = Vachali | first2 = P | last3 = Bernstein | first3 = P. S. | doi = 10.1039/c0pp00126k | pmc = 3938892 | bibcode = 2010PhPhS...9.1418L }}</ref>

Due to the commercial value of carotenoids, their ] has been studied extensively in both ]s and non-natural (heterologous) systems such as the bacteria ''Escherichia coli'' and yeast ''Saccharomyces cerevisiae''. Zeaxanthin biosynthesis proceeds from beta-carotene via the action of a single protein, known as a beta-carotene hydroxylase, that is able to add a hydroxyl group (-OH) to carbon 3 and 3′ of the beta-carotene molecule. Zeaxanthin biosynthesis therefore proceeds from beta-carotene to zeaxanthin (a di-hydroxylated product) via beta-cryptoxanthin (the mono hydroxylated intermediate). Although functionally identical, several distinct beta-carotene hydroxylase proteins are known.

Due to the nature of zeaxanthin, relative to ] (a carotenoid of significant commercial value) beta-carotene hydroxylase proteins have been studied extensively.<ref>{{cite journal|last=Scaife|first=Mark A.|author2=Ma, Cynthia A. |author3=Ninlayarn, Thanyanun |author4=Wright, Phillip C. |author5= Armenta, Roberto E. |display-authors=3 |title=Comparative Analysis of β-Carotene Hydroxylase Genes for Astaxanthin Biosynthesis|journal=Journal of Natural Products|date=22 May 2012|pages=1117–24|doi=10.1021/np300136t|pmid=22616944|volume=75|issue=6}}</ref>

==Relationship with diseases of the eye==
Several ] have provided preliminary evidence for high dietary intake of foods including lutein and zeaxanthin with lower incidence of ] (AMD), most notably the ] (AREDS2).<ref>{{cite web|url=https://nei.nih.gov/news/pressreleases/050513|title=NIH study provides clarity on supplements for protection against blinding eye disease|date=5 May 2013|access-date=10 August 2017|publisher=US National Eye Institute, National Institutes of Health, Bethesda, MD|archive-date=15 August 2019|archive-url=https://web.archive.org/web/20190815055737/https://nei.nih.gov/news/pressreleases/050513|url-status=dead}}</ref><ref>{{cite journal|pmc=4698241|year=2015|last1=Bernstein|first1=P. S.|title=Lutein, Zeaxanthin, and meso-Zeaxanthin: The Basic and Clinical Science Underlying Carotenoid-based Nutritional Interventions against Ocular Disease|journal=Progress in Retinal and Eye Research|volume=50|pages=34–66|last2=Li|first2=B|last3=Vachali|first3=P. P.|last4=Gorusupudi|first4=A|last5=Shyam|first5=R|last6=Henriksen|first6=B. S.|last7=Nolan|first7=J. M.|display-authors=3|doi=10.1016/j.preteyeres.2015.10.003|pmid=26541886}}</ref> Because foods high in one of these carotenoids tend to be high in the other, research does not separate effects of one from the other.<ref name="Krishnadev2010">{{cite journal |vauthors=Krishnadev N, Meleth AD, Chew EY | title = Nutritional supplements for age-related macular degeneration | journal = Current Opinion in Ophthalmology | volume = 21 | issue = 3 | pages = 184–9 |date=May 2010 | pmid = 20216418 | pmc = 2909501 | doi = 10.1097/ICU.0b013e32833866ee }}</ref><ref>{{cite journal |vauthors=SanGiovanni JP, Chew EY, Clemons TE, etal | title = 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 | journal = ] | volume = 125 | issue = 9 | pages = 1225–1232 |date=September 2007 | pmid = 17846363 | doi = 10.1001/archopht.125.9.1225 | doi-access = }}</ref>

* Three subsequent meta-analyses of dietary lutein and zeaxanthin concluded that these carotenoids lower the risk of progression from early stage AMD to late stage AMD.<ref>{{cite journal |vauthors=Liu R, Wang T, Zhang B, Qin L, Wu C, Li Q, Ma L |display-authors=3 |title=Lutein and zeaxanthin supplementation and association with visual function in age-related macular degeneration |journal=Invest. Ophthalmol. Vis. Sci. |volume=56 |issue=1 |pages=252–8 |year=2014 |pmid=25515572 |doi=10.1167/iovs.14-15553 }}</ref><ref>{{cite journal |vauthors=Wang X, Jiang C, Zhang Y, Gong Y, Chen X, Zhang M |display-authors=3 |title=Role of lutein supplementation in the management of age-related macular degeneration: meta-analysis of randomized controlled trials |journal=Ophthalmic Res. |volume=52 |issue=4 |pages=198–205 |year=2014 |pmid=25358528 |doi=10.1159/000363327 |s2cid=5055854 }}</ref><ref>{{cite journal |vauthors=Ma L, Dou HL, Wu YQ, Huang YM, Huang YB, Xu XR, Zou ZY, Lin XM |display-authors=3 |title=Lutein and zeaxanthin intake and the risk of age-related macular degeneration: a systematic review and meta-analysis |journal=Br. J. Nutr. |volume=107 |issue=3 |pages=350–9 |year=2012 |pmid=21899805 |doi=10.1017/S0007114511004260 |doi-access=free }}</ref>
* A 2023 (updated) ] review of 26 studies from several countries, however, concluded that ]s containing zeaxanthin and lutein have little to no influence on the progression of AMD.<ref name=":0">{{Cite journal |last1=Evans |first1=Jennifer R. |last2=Lawrenson |first2=John G. |date=2023-09-13 |title=Antioxidant vitamin and mineral supplements for slowing the progression of age-related macular degeneration |journal=The Cochrane Database of Systematic Reviews |volume=2023 |issue=9 |pages=CD000254 |doi=10.1002/14651858.CD000254.pub5 |issn=1469-493X |pmc=10498493 |pmid=37702300 }}</ref> In general, there remains insufficient evidence to assess the effectiveness of dietary or supplemental zeaxanthin or lutein in treatment or prevention of early AMD.<ref name=LPI/><ref name="Krishnadev2010" /><ref name=":0" />

As for cataracts, two meta-analyses confirm a correlation between high serum concentrations of lutein and zeaxanthin and a decrease in the risk of nuclear cataract, but not cortical or subcapsular cataract. The reports did not separate a zeaxanthin effect from a lutein effect.<ref>{{cite journal |vauthors=Liu XH, Yu RB, Liu R, Hao ZX, Han CC, Zhu ZH, Ma L |display-authors=3 |title=Association between lutein and zeaxanthin status and the risk of cataract: a meta-analysis |journal=Nutrients |volume=6 |issue=1 |pages=452–65 |year=2014 |pmid=24451312 |pmc=3916871 |doi=10.3390/nu6010452 |doi-access=free }}</ref><ref>{{cite journal |vauthors=Ma L, Hao ZX, Liu RR, Yu RB, Shi Q, Pan JP |display-authors=3 |title=A dose-response meta-analysis of dietary lutein and zeaxanthin intake in relation to risk of age-related cataract |journal=Graefes Arch. Clin. Exp. Ophthalmol. |volume=252 |issue=1 |pages=63–70 |year=2014 |pmid=24150707 |doi=10.1007/s00417-013-2492-3 |s2cid=13634941 }}</ref> The AREDS2 trial enrolled subjects at risk for progression to advanced age-related macular degeneration. Overall, the group getting lutein (10&nbsp;mg) and zeaxanthin (2&nbsp;mg) did not reduce the need for cataract surgery.<ref>{{cite journal |vauthors=Chew EY, SanGiovanni JP, Ferris FL, Wong WT, Agron E, Clemons TE, Sperduto R, Danis R, Chandra SR, Blodi BA, Domalpally A, Elman MJ, Antoszyk AN, Ruby AJ, Orth D, Bressler SB, Fish GE, Hubbard GB, Klein ML, Friberg TR, Rosenfeld PJ, Toth CA, Bernstein P |display-authors=3 |title=Lutein/zeaxanthin for the treatment of age-related cataract: AREDS2 randomized trial report no. 4 |journal=JAMA Ophthalmol |volume=131 |issue=7 |pages=843–50 |year=2013 |pmid=23645227 |doi=10.1001/jamaophthalmol.2013.4412 |pmc=6774801 |doi-access=free }}</ref> Any benefit is more likely to be apparent in subpopulations of individuals exposed to high oxidative stress, such as heavy smokers, alcoholics or those with low dietary intake of carotenoid-rich foods.<ref>{{cite journal |vauthors=Fernandez MM, Afshari NA | title = Nutrition and the prevention of cataracts | journal = Current Opinion in Ophthalmology | volume = 19 | issue = 1 | pages = 66–70 |date=January 2008 | pmid = 18090901 | doi = 10.1097/ICU.0b013e3282f2d7b6 | s2cid = 25735519 }}</ref>

In 2005, the US ] rejected a ''Qualified Health Claims'' application by Xangold, citing insufficient evidence supporting the use of a lutein- and zeaxanthin-containing supplement in prevention of AMD.<ref>{{cite web|publisher=US FDA, Qualified Health Claims|url=https://www.fda.gov/Food/IngredientsPackagingLabeling/LabelingNutrition/ucm073291.htm |title=Letter of Denial - Xangold Lutein Esters, Lutein, or Zeaxanthin and Reduced Risk of Age-related Macular Degeneration or Cataract Formation (Docket No. 2004Q-0180|date=19 December 2005}}</ref> Dietary supplement companies in the U.S. are allowed to sell lutein and lutein plus zeaxanthin products using '']'', such as "Helps maintain eye health", as long as the FDA disclaimer statement ("These statements have not been evaluated...") is on the label. In Europe, as recently as 2014, the ] reviewed and rejected claims that lutein or lutein plus zeaxanthin improved vision.<ref>{{cite journal|title=Scientific Opinion on the substantiation of a health claim related to a combination of lutein and zeaxanthin and improved vision under bright light conditions pursuant to Article 13(5) of Regulation (EC) No 1924/2006|journal=EFSA Journal|volume=12|issue=7|year=2014|pages=3753|issn=1831-4732|doi=10.2903/j.efsa.2014.3753|doi-access=free}}</ref>

==Natural occurrence==
Zeaxanthin is the pigment that gives ], ], ], ], and many other plants their characteristic colors of red, orange or yellow.<ref name=LPI/><ref name=":0" /> ] is also a rich source and can serve as a dietary supplement.<ref>{{Cite journal | last1 = Yu | first1 = B. | last2 = Wang | first2 = J. | last3 = Suter | first3 = P. M. | last4 = Russell | first4 = R. M. | last5 = Grusak | first5 = M. A. | last6 = Wang | first6 = Y. | last7 = Wang | first7 = Z. | last8 = Yin | first8 = S. | last9 = Tang | first9 = G. | doi = 10.1017/S0007114511005885 | title = Spirulina is an effective dietary source of zeaxanthin to humans | journal = British Journal of Nutrition | volume = 108 | issue = 4 | pages = 611–619 | year = 2012 | pmid = 22313576 | display-authors=3 | doi-access = free }}</ref> Zeaxanthin breaks down to form ] and ], which are responsible for the taste and aroma of saffron.<ref>{{Cite journal|title = Novel carotenoid cleavage dioxygenase catalyzes the first dedicated step in saffron crocin biosynthesis|journal = Proceedings of the National Academy of Sciences|date = 2014-08-19|issn = 0027-8424|pmc = 4143034|pmid = 25097262|pages = 12246–12251|volume = 111|issue = 33|doi = 10.1073/pnas.1404629111|language = en|first1 = Sarah|last1 = Frusciante|first2 = Gianfranco|last2 = Diretto|first3 = Mark|last3 = Bruno|first4 = Paola|last4 = Ferrante|first5 = Marco|last5 = Pietrella|first6 = Alfonso|last6 = Prado-Cabrero|first7 = Angela|last7 = Rubio-Moraga|first8 = Peter|last8 = Beyer|first9 = Lourdes|last9 = Gomez-Gomez|display-authors=3|bibcode = 2014PNAS..11112246F|doi-access = free}}</ref>

Dark green ]s, such as ], ], ], ], ], ], ] and ] are rich in lutein<ref name=LPI/><ref>{{cite web|url=http://nutritiondata.self.com/foods-000138000000000000000-1w.html|title=Foods highest in lutein-zeaxanthin per 100 grams|publisher=Conde Nast for the USDA National Nutrient Database, release SR-21|date=2014|access-date=23 December 2015}}</ref> but contain little to no zeaxanthin, with the exception of scallions cooked in oil.<ref name=perry2009/> Orange bell peppers (but not green, red, or yellow) are rich in zeaxanthin.<ref name=perry2009/>

{| class="wikitable sortable"
|+ Lutein and zeaxanthin concentrations in fruits and vegetables (μg / 100 g)<ref name=perry2009>{{cite journal |author1=Alisa Perry |author2=Helen Rasmussen |author3=Elizabeth J. Johnson |title=Xanthophyll (lutein, zeaxanthin) content in fruits, vegetables and corn and egg products |journal=Journal of Food Composition and Analysis |date=Feb 2009 |volume=22 |issue=1 |pages=9–15 |doi=10.1016/j.jfca.2008.07.006 |url=https://www.sciencedirect.com/science/article/abs/pii/S0889157508001336 |access-date=4 February 2024 |ref=perry2009}}</ref>
|-
! Food (100 g) !! Lutein ''trans'' (μg) !! Zeaxanthin ''trans'' (μg)
|-
| Spinach, cooked || 12,640 || 0
|-
| Spinach, raw || 6,603 || 0
|-
| Kale, cooked || 8,884 || 0
|-
| Cilantro || 7,703 || 0
|-
| Scallions, cooked in oil || || 2,488
|-
| Scallions, raw || 782 || 0
|-
| Bell pepper, green || 173 || 0
|-
| Bell pepper, orange || 208 || 1,665
|-
| Bell pepper, red || 0 || 22
|-
| Bell pepper, yellow || 139 || 18
|-
| Cornmeal, yellow || 1 || 531
|-
| Cornmeal, white || 13 || 13
|-
| Corn, cooked from frozen || 202 || 202
|-
| Tortilla, corn || 276 || 255
|}

==Safety==
An ] level for zeaxanthin was proposed as 0.75&nbsp;mg/kg of body weight/day, or 53&nbsp;mg/day for a 70&nbsp;kg adult.<ref name="pmid26885380"><!--This is a review article.-->{{cite journal | vauthors = Edwards JA | title = Zeaxanthin: Review of Toxicological Data and Acceptable Daily Intake | journal = Journal of Ophthalmology | volume = 2016 | pages = 1–15 | year = 2016 | pmid = 26885380 | pmc = 4738691 | doi = 10.1155/2016/3690140 | quote =<br/>• In their evaluation of the safety of synthetic zeaxanthin as a Novel Food, the EFSA NDA Scientific Panel applied a 200-fold safety factor to this NOAEL to define an ADI of 0.75 mg/kg bw/day, or 53 mg/day for a 70 kg adult.<br/>• Formulated zeaxanthin was not mutagenic or clastogenic in a series of in vitro and in vivo tests for genotoxicity.<br/>• Information from human intervention studies also supports that an intake higher than 2 mg/day is safe, and an intake level of 20 mg/day for up to 6 months was without adverse effect.| doi-access = free }}</ref> In humans, an intake of 20&nbsp;mg/day for up to six months had no ].<ref name="pmid26885380"/> As of 2016, neither the U.S. Food and Drug Administration nor the European Food Safety Authority had set a Tolerable Upper Intake Level (UL) for lutein or zeaxanthin.

==References==
{{Reflist | 2}}

{{Carotenoids}}

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