Zeaxanthin

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Zeaxanthin is one of the two carotenoids contained within the retina.

Template:PubChem Row
Zeaxanthin
Zeaxanthin
General
Systematic 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; ß,ß-carotene-3,3'-diol
Molecular formula C40H56O2
SMILES CC1CC(O)CC(C)(C)C=1C=CC(C)=CC=CC(C)=CC=
CC=C(C)C=CC=C(C)C=CC2=C(C)CC(O)CC2(C)C
Molar mass 568.88 g/mol
Appearance orange-red
CAS number 144-68-3
EINECS 205-636-4
Properties
Density and phase  ? g/cm³, ?
Solubility in water insol.
Melting point 215.5 °C (488.7 K)
Boiling point  ? °C (? K)
Acidity (pKa)  ?
Basicity (pKb)  ?
Chiral rotation [α]D  ?°
Viscosity  ? cP at ? °C
Hazards
MSDS External MSDS
Main hazards  ?
NFPA 704
Flash point  ? °C
R/S statement R: ?
S: ?
RTECS number  ?
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Other anions  ?
Other cations  ?
Related ?  ?
Related compounds lutein
xanthophyll
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

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.

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.

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


References


bg:Зеаксантин

de:Zeaxanthin it:Zeaxantina nl:Citranaxanthine


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