Zeaxanthin
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| Category | Others |
| Catalog number | BBF-05806 |
| CAS | 144-68-3 |
| Molecular Weight | 568.89 |
| Molecular Formula | C40H56O2 |
| Purity | ≥97% |
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Description
Zeaxanthin is a carotenoid xanthophyll that plays a role in the xanthophyll cycle. Zeaxanthin is a pigment that gives paprika (made from bell peppers), corn, saffron, wolfberries, and many other plants and microbes their characteristic color. It is used for eye health.
Nutritional supplement in health care products.
Specification
| Synonyms | Anchovyxanthin; Xanthophyll 3; Zeaxanthol; all-trans-Zeaxanthin; Beta,beta-carotene-3,3'-diol; all-E-Zeaxanthin; all-trans-3R,3'R-Zeaxanthin; all-trans-Anchovyxanthin; Luteinofta; Optisharp; (3R,3'R)-Dihydroxy-β-carotene; (3R,3'R)-Zeaxanthin; (3R,3'R)-β,β-Carotene-3,3'-diol; (3R,3'R)-all-trans-β-Carotene-3,3'-diol |
| Storage | Store at -86°C under inert atmosphere |
| IUPAC Name | (1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol |
| Canonical SMILES | CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(CC(CC2(C)C)O)C)C)C |
| 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 |
| InChI Key | JKQXZKUSFCKOGQ-QAYBQHTQSA-N |
Properties
| Appearance | Light Orange to Dark Red Solid |
| Application | Ingredient of health care products. |
| Boiling Point | 711.4±55.0°C at 760 mmHg |
| Melting Point | 200-220°C |
| Density | 1.0±0.1 g/cm3 |
| Solubility | Soluble in Chloroform (Slightly), Methanol (Slightly) |
Reference Reading
1. A Brief Overview of Dietary Zeaxanthin Occurrence and Bioaccessibility
Cristina Tudor, Adela Pintea Molecules. 2020 Sep 6;25(18):4067. doi: 10.3390/molecules25184067.
As it exhibits no provitamin A activity, the dietary intake of zeaxanthin is not considered essential. However, its contribution to ocular health has long been acknowledged. Numerous publications emphasize the importance of zeaxanthin alongside lutein in ocular diseases such as cataracts and age-related macular degeneration which constitute an important health concern, especially among the elderly. Considering that the average dietary ratio of lutein to zeaxanthin favors the first, more bioaccessible food sources of zeaxanthin that can hinder the development and progression of the above-mentioned disorders are of great interest. In this paper, a brief overview of the more recent state of knowledge as regards dietary sources together with their respective zeaxanthin bioaccessibility assessed through a standardized in vitro digestion method was provided.
2. Lutein and Zeaxanthin and Their Roles in Age-Related Macular Degeneration-Neurodegenerative Disease
Małgorzata Mrowicka, Jerzy Mrowicki, Ewa Kucharska, Ireneusz Majsterek Nutrients. 2022 Feb 16;14(4):827. doi: 10.3390/nu14040827.
Lutein and zeaxanthin belong to the xanthophyll family of carotenoids, which are pigments produced by plants. Structurally, they are very similar, differing only slightly in the arrangement of atoms. Key sources of these carotenoids include kale, savoy cabbage, spinach, broccoli, peas, parsley, corn, and egg yolks. The recommended daily intake of lutein is approximately 10.0 mg and that of zeaxanthin is 2 mg. Lutein intake in adults varies, with average intakes being 1-2 mg/day. Due to the lack of synthesis of consumption of these compounds in humans, these substances are extremely important for the proper functioning of certain organs of the body (eye, skin, heart, intestines). Eating a lot of dark leafy vegetables and some fruits can help to prevent our bodies from developing diseases. The protective effects of carotenoids are mainly related to their defense against oxidative stress and their ability to scavenge free radicals. Lutein and zeaxanthin are the only dietary carotenoids that accumulate in the retina, specifically the macula, and are called macular pigments. These carotenoids are concentrated by the action of specific binding proteins such as StARD3, which binds lutein, and GSTP1, which binds zeaxanthin and its dietary metabolite, mesozeaxanthin. It has been shown that supportive therapy with lutein and zeaxanthin can have a beneficial effect in delaying the progression of eye diseases such as age-related macular degeneration (AMD) and cataracts. This article presents the current state of knowledge on the role of lutein and zeaxanthin, especially from human studies targeting their metabolism and bioavailability, with recommendations to consume xanthophyll-rich foods.
3. Why is Zeaxanthin the Most Concentrated Xanthophyll in the Central Fovea?
Justyna Widomska, John Paul SanGiovanni, Witold K Subczynski Nutrients. 2020 May 7;12(5):1333. doi: 10.3390/nu12051333.
Diet-based xanthophylls (zeaxanthin and lutein) are conditionally essential polar carotenoids preferentially accreted in high concentrations (1 mM) to the central retina, where they have the capacity to impart unique physiologically significant biophysical biochemical properties implicated in cell function, rescue, and survival. Macular xanthophylls interact with membrane-bound proteins and lipids to absorb/attenuate light energy, modulate oxidative stress and redox balance, and influence signal transduction cascades implicated in the pathophysiology of age-related macular degeneration. There is exclusive transport, sequestration, and appreciable bioamplification of macular xanthophylls from the circulating carotenoid pool to the retina and within the retina to regions required for high-resolution sensory processing. The distribution of diet-based macular xanthophylls and the lutein metabolite meso-zeaxanthin varies considerably by retinal eccentricity. Zeaxanthin concentrations are 2.5-fold higher than lutein in the cone-dense central fovea. This is an ~20-fold increase in the molar ratio relative to eccentric retinal regions with biochemically detectable macular xanthophylls. In this review, we discuss how the differences in the specific properties of lutein and zeaxanthin could help explain the preferential accumulation of zeaxanthin in the most vulnerable region of the macula.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
