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Human Metabolome Database Version 2.5

 

Showing metabocard for Zeaxanthin (HMDB02789)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-05-22 16:12:10
Update Date 2009-08-04 11:31:25
Accession Number HMDB02789
Secondary Accession Numbers Not Available
Common Name Zeaxanthin
Description Zeaxanthin is a carotenoid xanthophyll and is one of the most common carotenoid 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 Carotenoids are among the most common pigments in nature and are natural lipid soluble antioxidants. Zeaxanthin is one of the two carotenoids (the other is lutein) that accumulate in the eye lens and macular region of the retina with concentrations in the macula greater than those found in plasma and other tissues. 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. A relationship between macular pigment optical density, a marker of lutein and zeaxanthin concentration in the macula, and lens optical density, an antecedent of cataractous changes, has been suggested. The xanthophylls may act to protect the eye from ultraviolet phototoxicity via quenching reactive oxygen species and/or other mechanisms. Some observational studies have shown that generous intakes of lutein and zeaxanthin, particularly from certain xanthophyll-rich foods like spinach, broccoli and eggs, are associated with a significant reduction in the risk for cataract (up to 20%) and for age-related macular degeneration (up to 40%). While the pathophysiology of cataract and age-related macular degeneration is complex and contains both environmental and genetic components, research studies suggest dietary factors including antioxidant vitamins and xanthophylls may contribute to a reduction in the risk of these degenerative eye diseases. Further research is necessary to confirm these observations. (PMID: 11023002)
Synonyms
  1. (3R,3'R)-Zeaxanthin
  2. Anchovyxanthin
  3. Xanthophyll 3
  4. Zeaxanthin
  5. Zeaxanthol
  6. all-trans-Anchovyxanthin
  7. all-trans-Zeaxanthin
Chemical IUPAC Name (3R,3'R) b,b-carotene-3,3'-diol
Chemical Formula C40H56O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Miscellaneous
Class
  • Retinoids
Sub Class
  • Xanthinoids
Family
  • Plant Metabolite
Species
  • secondary alcohol
  • alkene
Biofunction
—
Application
—
Source
  • Exogenous
Average Molecular Weight 568.871
Monoisotopic Molecular Weight 568.428040
Isomeric SMILES CC(C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C
Canonical SMILES CC(C=CC=C(C)C=CC1=C(C)CC(O)CC1(C)C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)CC(O)CC1(C)C
KEGG Compound ID C06098 Link Image
BioCyc ID CPD1F-130 Link Image
BiGG ID Not Available
Wikipedia Link Zeaxanthin Link Image
NuGOwiki Link HMDB02789 Link Image
Metagene Link HMDB02789 Link Image
METLIN ID 3602 Link Image
PubChem Compound 5280899 Link Image
PubChem Substance 8616435 Link Image
ChEBI ID 27547 Link Image
CAS Registry Number 144-68-3
InChI Identifier 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
Synthesis Reference Paus, Joachim; Kriegl, Wolfgang. Process for the preparation of zeaxanthin and its intermediates. Eur. Pat. Appl. (1998), 19 pp.
Melting Point (Experimental) 215.5 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 3.58e-15 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]; 6.49e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 8.30 [Predicted by ALOGPS]; 7.177 [Predicted by PubChem via XLOGP]; 14.95 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location
  • Blood
Tissue Location
Tissue References
Adipose Tissue —
Eye Lens —
Lens —
Retina —
Spleen —
Concentrations (Normal)
Biofluid Blood
Value 0.032 +/- 0.023 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments After receiving a supplement consisting of 12 mg lutein and 1 mg zeaxanthin
References
  • Trieschmann M, Beatty S, Nolan JM, Hense HW, Heimes B, Austermann U, Fobker M, Pauleikhoff D: Changes in macular pigment optical density and serum concentrations of its constituent carotenoids following supplemental lutein and zeaxanthin: the LUNA study. Exp Eye Res. 2007 Apr;84(4):718-28. Epub 2006 Dec 19. [PubMed Link Image]
Biofluid Blood
Value 0.04 +/- 0.04 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Porrini M, Riso P, Brusamolino A, Berti C, Guarnieri S, Visioli F: Daily intake of a formulated tomato drink affects carotenoid plasma and lymphocyte concentrations and improves cellular antioxidant protection. Br J Nutr. 2005 Jan;93(1):93-9. [PubMed Link Image]
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways Not Available
General References
  1. Wenzel AJ, Gerweck C, Barbato D, Nicolosi RJ, Handelman GJ, Curran-Celentano J: A 12-wk egg intervention increases serum zeaxanthin and macular pigment optical density in women. J Nutr. 2006 Oct;136(10):2568-73. [PubMed Link Image]
  2. Rapp LM, Maple SS, Choi JH: Lutein and zeaxanthin concentrations in rod outer segment membranes from perifoveal and peripheral human retina. Invest Ophthalmol Vis Sci. 2000 Apr;41(5):1200-9. [PubMed Link Image]
  3. Khachik F, Bernstein PS, Garland DL: Identification of lutein and zeaxanthin oxidation products in human and monkey retinas. Invest Ophthalmol Vis Sci. 1997 Aug;38(9):1802-11. [PubMed Link Image]
  4. Handelman GJ, Nightingale ZD, Lichtenstein AH, Schaefer EJ, Blumberg JB: Lutein and zeaxanthin concentrations in plasma after dietary supplementation with egg yolk. Am J Clin Nutr. 1999 Aug;70(2):247-51. [PubMed Link Image]
  5. Dasch B, Fuhs A, Schmidt J, Behrens T, Meister A, Wellmann J, Fobker M, Pauleikhoff D, Hense HW: Serum levels of macular carotenoids in relation to age-related maculopathy: the Muenster Aging and Retina Study (MARS). Graefes Arch Clin Exp Ophthalmol. 2005 Oct;243(10):1028-35. Epub 2005 Oct 20. [PubMed Link Image]
  6. Bone RA, Landrum JT, Friedes LM, Gomez CM, Kilburn MD, Menendez E, Vidal I, Wang W: Distribution of lutein and zeaxanthin stereoisomers in the human retina. Exp Eye Res. 1997 Feb;64(2):211-8. [PubMed Link Image]
  7. Chitchumroonchokchai C, Failla ML: Hydrolysis of zeaxanthin esters by carboxyl ester lipase during digestion facilitates micellarization and uptake of the xanthophyll by Caco-2 human intestinal cells. J Nutr. 2006 Mar;136(3):588-94. [PubMed Link Image]
  8. Khachik F: An efficient conversion of (3R,3'R,6'R)-lutein to (3R,3'S,6'R)-lutein (3'-epilutein) and (3R,3'R)-zeaxanthin. J Nat Prod. 2003 Jan;66(1):67-72. [PubMed Link Image]
  9. Hammond BR Jr, Wooten BR, Snodderly DM: Density of the human crystalline lens is related to the macular pigment carotenoids, lutein and zeaxanthin. Optom Vis Sci. 1997 Jul;74(7):499-504. [PubMed Link Image]
  10. Johnson EJ, Hammond BR, Yeum KJ, Qin J, Wang XD, Castaneda C, Snodderly DM, Russell RM: Relation among serum and tissue concentrations of lutein and zeaxanthin and macular pigment density. Am J Clin Nutr. 2000 Jun;71(6):1555-62. [PubMed Link Image]
  11. Mares-Perlman JA, Millen AE, Ficek TL, Hankinson SE: The body of evidence to support a protective role for lutein and zeaxanthin in delaying chronic disease. Overview. J Nutr. 2002 Mar;132(3):518S-524S. [PubMed Link Image]
  12. Sies H, Stahl W: Non-nutritive bioactive constituents of plants: lycopene, lutein and zeaxanthin. Int J Vitam Nutr Res. 2003 Mar;73(2):95-100. [PubMed Link Image]
  13. Wikipedia Link Image