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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:10 UTC
Update Date2019-07-23 05:45:37 UTC
HMDB IDHMDB0002789
Secondary Accession Numbers
  • HMDB02789
Metabolite Identification
Common NameZeaxanthin
DescriptionZeaxanthin 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 ). Zeaxanthin has been found to be a microbial metabolite, it can be produced by Algibacter, Aquibacter, Escherichia, Flavobacterium, Formosa, Gramella, Hyunsoonleella, Kordia, Mesoflavibacter, Muricauda, Nubsella, Paracoccus, Siansivirga, Sphingomonas, Zeaxanthinibacter and yeast (https://reader.elsevier.com/reader/sd/pii/S0924224417302571?token=DE6BC6CC7DCDEA6150497AA3E375097A00F8E0C12AE03A8E420D85D1AC8855E62103143B5AE0B57E9C5828671F226801). It is a marker for the activity of Bacillus subtilis and/or Pseudomonas aeruginosa in the intestine. Higher levels are associated with higher levels of Bacillus or Pseudomonas. (PMID: 17555270 ; PMID: 12147474 )
Structure
Data?1563860737
Synonyms
ValueSource
(3R,3'r)-Dihydroxy-beta,beta-caroteneChEBI
all-trans-beta-Carotene-3,3'-diolChEBI
all-trans-ZeaxanthinChEBI
AnchovyxanthinChEBI
beta,beta-Carotene-3,3'-diolChEBI
(3R,3'r)-beta,beta-Carotene-3,3'-diolKegg
(3R,3'r)-Dihydroxy-b,b-caroteneGenerator
(3R,3'r)-Dihydroxy-β,β-caroteneGenerator
all-trans-b-Carotene-3,3'-diolGenerator
all-trans-Β-carotene-3,3'-diolGenerator
b,b-Carotene-3,3'-diolGenerator
Β,β-carotene-3,3'-diolGenerator
(3R,3'r)-b,b-Carotene-3,3'-diolGenerator
(3R,3'r)-Β,β-carotene-3,3'-diolGenerator
Beta Carotene 3,3' diolMeSH
beta-Carotene-3,3'-diolMeSH
3R,3'r-ZeaxanthinMeSH
ZeaxanthinsMeSH
3R,3'r ZeaxanthinMeSH
(3R,3'r)-ZeaxanthinHMDB
all-trans-AnchovyxanthinHMDB
Xanthophyll 3HMDB
ZeaxantholHMDB
Chemical FormulaC40H56O2
Average Molecular Weight568.886
Monoisotopic Molecular Weight568.428031043
IUPAC Name(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol
Traditional Namezeaxanthin
CAS Registry Number144-68-3
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=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
InChI Identifier
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 KeyJKQXZKUSFCKOGQ-QAYBQHTQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point215.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00065 g/LALOGPS
logP8.3ALOGPS
logP8.35ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.91ChemAxon
pKa (Strongest Basic)-0.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity194.95 m³·mol⁻¹ChemAxon
Polarizability73.47 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2000190000-2cc8481518a353268253JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3000049000-45b1b78e4b208f89e457JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0111190000-a3e4a4d0d67ea298da49JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-0649330000-191e0ac14dcad154b4b3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-0449130000-5644e7cc2bbfa6ef09f0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-8f8c6909e2b7e1022ce9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-421f46802deab60d756dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0553390000-883720ed84543eb475e2JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Adipose Tissue
  • Eye Lens
  • Lens
  • Retina
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.22 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.25 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.114 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.382 +/- 0.00600 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.310 +/- 0.110 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.320 +/- 0.100 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.390 +/- 0.180 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.400 +/- 0.180 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.153 +/- 0.160 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.360 +/- 0.160 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.560 +/- 0.270 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.139 +/- 0.130 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.350 +/- 0.130 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.350 +/- 0.140 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.520 +/- 0.230 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.163 +/- 0.190 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.438 +/- 0.161 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.374 +/- 0.150 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.493 +/- 0.181 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.399 +/- 0.121 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.290 +/- 0.120 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.390 +/- 0.140 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.480 +/- 0.180 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.26 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.26 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified460 +/- 150 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.329 +/- 0.139 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.341 +/- 0.168 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.24 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.032 +/- 0.023 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.27 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.128 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.305 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.445 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.47 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.36 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.384 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.436 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0344 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.039 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0530 +/- 0.0200 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0680 +/- 0.0400 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.299 +/- 0.123 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.316 +/- 0.109 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.360 +/- 0.450 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.394 +/- 0.179 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.09 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.32 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.33 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.395 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.401 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.492 uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified0.0600 +/- 0.0300 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0850 +/- 0.0340 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.113 +/- 0.0492 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.128 +/- 0.0529 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.216 +/- 0.0861 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.260 +/- 0.0800 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.315 +/- 0.128 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.328 +/- 0.165 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.330 +/- 0.0900 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.383 +/- 0.183 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.411 +/- 0.140 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.432 +/- 0.204 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.09 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.3 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.32 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.413 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.498 uMChildren (1-13 years old)MaleNormal details
BloodDetected and Quantified0.0390 +/- 0.0150 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0660 +/- 0.0280 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0700 +/- 0.0300 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.240 +/- 0.0700 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.251 +/- 0.111 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.269 +/- 0.123 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.278 +/- 0.118 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.316 +/- 0.143 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.367 +/- 0.176 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified420 +/- 140 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified490 +/- 190 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.04 +/- 0.04 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.126 +/- 0.110 uMAdult (>18 years old)Not Specified
Obese
details
BloodDetected and Quantified0.157 +/- 0.160 uMAdult (>18 years old)Not Specified
Overweight
details
BloodDetected and Quantified0.0700 +/- 0.0300 uMAdult (>18 years old)BothType I diabetes details
Associated Disorders and Diseases
Disease References
Obesity
  1. Vioque J, Weinbrenner T, Asensio L, Castello A, Young IS, Fletcher A: Plasma concentrations of carotenoids and vitamin C are better correlated with dietary intake in normal weight than overweight and obese elderly subjects. Br J Nutr. 2007 May;97(5):977-86. [PubMed:17408529 ]
Diabetes mellitus type 1
  1. Granado-Lorencio F, Olmedilla-Alonso B, Blanco-Navarro I, Botella-Romero F, Simal-Anton A: Assessment of carotenoid status and the relation to glycaemic control in type I diabetics: a follow-up study. Eur J Clin Nutr. 2006 Aug;60(8):1000-8. Epub 2006 Feb 1. [PubMed:16452910 ]
Associated OMIM IDs
DrugBank IDDB11176
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000931
Chemspider IDNot Available
KEGG Compound IDC06098
BioCyc IDCPD1F-130
BiGG IDNot Available
Wikipedia LinkZeaxanthin
METLIN IDNot Available
PubChem Compound5280899
PDB IDNot Available
ChEBI ID27547
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferencePaus, Joachim; Kriegl, Wolfgang. Process for the preparation of zeaxanthin and its intermediates. Eur. Pat. Appl. (1998), 19 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
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:16988128 ]
  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:10752961 ]
  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:9286269 ]
  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:10426702 ]
  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:15909159 ]
  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:9176055 ]
  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:16484529 ]
  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:12542348 ]
  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:9293517 ]
  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:10837298 ]
  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:11880585 ]
  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:12747216 ]
  13. Moeller SM, Jacques PF, Blumberg JB: The potential role of dietary xanthophylls in cataract and age-related macular degeneration. J Am Coll Nutr. 2000 Oct;19(5 Suppl):522S-527S. [PubMed:11023002 ]
  14. Idris EE, Iglesias DJ, Talon M, Borriss R: Tryptophan-dependent production of indole-3-acetic acid (IAA) affects level of plant growth promotion by Bacillus amyloliquefaciens FZB42. Mol Plant Microbe Interact. 2007 Jun;20(6):619-26. doi: 10.1094/MPMI-20-6-0619. [PubMed:17555270 ]
  15. Patten CL, Glick BR: Role of Pseudomonas putida indoleacetic acid in development of the host plant root system. Appl Environ Microbiol. 2002 Aug;68(8):3795-801. [PubMed:12147474 ]