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Record Information
StatusDetected and Quantified
Creation Date2006-05-22 15:12:43 UTC
Update Date2020-10-09 21:03:02 UTC
Secondary Accession Numbers
  • HMDB03233
Metabolite Identification
Common NameLutein
DescriptionLutein is a common carotenoid xanthophyll found in nature. Carotenoids are among the most common pigments in nature and are natural lipid-soluble antioxidants. Lutein is one of the two carotenoids (the other is zeaxanthin) 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 cataracts (up to 20%) and 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 ).
e 161bChEBI
gamma LuteinMeSH
Lutein FMeSH
Lutein gMeSH
Lutein, gammaMeSH
Chemical FormulaC40H56O2
Average Molecular Weight568.886
Monoisotopic Molecular Weight568.428031043
IUPAC Name(1R,4R)-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-2-en-1-ol
Traditional Namecarotenoid
CAS Registry Number127-40-2
InChI Identifier
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
  • Xanthophyll
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Biological role:

Industrial application:

Physical Properties
Experimental Properties
Melting Point196 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.00073 g/LALOGPS
pKa (Strongest Acidic)18.22ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity195.06 m³·mol⁻¹ChemAxon
Polarizability74.26 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0111190000-56a7b3ad9850d88a093aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-0729640000-fa9f79f8a73fa60b8abfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-2439510000-8c70ee5c9af7440a4672Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-e64043a148b331ba05a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-a48901fc52e8e64be250Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0522590000-ed879e2e3d350ac0e502Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Adipose Tissue
  • Adrenal Gland
  • Epidermis
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Neuron
  • Ovary
  • Placenta
  • Retina
  • Spleen
  • Testis
Normal Concentrations
BloodDetected and Quantified0.180 +/- 0.0800 uMAdult (>18 years old)Female
BloodDetected and Quantified0.200 +/- 0.100 uMAdult (>18 years old)Male
BloodDetected and Quantified0.180 +/- 0.0700 uMAdult (>18 years old)Female
BloodDetected and Quantified0.140 +/- 0.0500 uMAdult (>18 years old)Male
BloodDetected and Quantified0.156 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.163 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.198 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.180 +/- 0.0900 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.310 +/- 0.160 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.350 +/- 0.200 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.44 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.270 +/- 0.110 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.304 +/- 0.111 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.320 +/- 0.160 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.329 +/- 0.123 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified270.360 +/- 108.636 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.38 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.174 +/- 0.0640 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.251 +/- 0.0980 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.280 +/- 0.100 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified275.633 +/- 98.792 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.320 +/- 0.230 uMChildren (1 - 13 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.52 (0.24-0.79) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.53 +/- 0.26 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.49 +/- 0.23 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified0.210 +/- 0.0900 uMAdult (>18 years old)BothType I diabetes details
BloodDetected and Quantified0.310 +/- 0.110 uMChildren (1 - 13 years old)Not SpecifiedObese details
BloodDetected and Quantified0.390 +/- 0.150 uMChildren (1 - 13 years old)Not SpecifiedOverweight details
Associated Disorders and Diseases
Disease References
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 ]
  1. Burrows TL, Warren JM, Colyvas K, Garg ML, Collins CE: Validation of overweight children's fruit and vegetable intake using plasma carotenoids. Obesity (Silver Spring). 2009 Jan;17(1):162-8. doi: 10.1038/oby.2008.495. Epub 2008 Nov 6. [PubMed:18997681 ]
Associated OMIM IDs
DrugBank IDDB00137
Phenol Explorer Compound IDNot Available
FooDB IDFDB015471
KNApSAcK IDC00003776
Chemspider ID4444655
KEGG Compound IDC08601
BioCyc IDCPD1F-119
BiGG IDNot Available
Wikipedia LinkLutein
METLIN IDNot Available
PubChem Compound5281243
PDB IDNot Available
ChEBI ID28838
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000416
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Reboul E, Abou L, Mikail C, Ghiringhelli O, Andre M, Portugal H, Jourdheuil-Rahmani D, Amiot MJ, Lairon D, Borel P: Lutein transport by Caco-2 TC-7 cells occurs partly by a facilitated process involving the scavenger receptor class B type I (SR-BI). Biochem J. 2005 Apr 15;387(Pt 2):455-61. [PubMed:15554873 ]
  2. Park JS, Chew BP, Wong TS: Dietary lutein absorption from marigold extract is rapid in BALB/c mice. J Nutr. 1998 Oct;128(10):1802-6. [PubMed:9772152 ]
  3. Chitchumroonchokchai C, Schwartz SJ, Failla ML: Assessment of lutein bioavailability from meals and a supplement using simulated digestion and caco-2 human intestinal cells. J Nutr. 2004 Sep;134(9):2280-6. [PubMed:15333717 ]
  4. 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 ]
  5. Eichler O, Sies H, Stahl W: Divergent optimum levels of lycopene, beta-carotene and lutein protecting against UVB irradiation in human fibroblastst. Photochem Photobiol. 2002 May;75(5):503-6. [PubMed:12017476 ]
  6. Chen L, Collins XH, Tabatabai LB, White WS: Use of a 13C tracer to investigate lutein as a ligand for plasma transthyretin in humans. Lipids. 2005 Oct;40(10):1013-22. [PubMed:16382573 ]
  7. 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 ]
  8. 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 ]
  9. Granado F, Olmedilla B, Blanco I: Nutritional and clinical relevance of lutein in human health. Br J Nutr. 2003 Sep;90(3):487-502. [PubMed:14513828 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. Bruch-Gerharz D, Stahl W, Gerharz CD, Megahed M, Wingerath T, Sies H, Ruzicka T: Accumulation of the xanthophyll lutein in skin amyloid deposits of systemic amyloidosis (al type). J Invest Dermatol. 2001 Jan;116(1):196-7. [PubMed:11168818 ]
  16. Goodrow EF, Wilson TA, Houde SC, Vishwanathan R, Scollin PA, Handelman G, Nicolosi RJ: Consumption of one egg per day increases serum lutein and zeaxanthin concentrations in older adults without altering serum lipid and lipoprotein cholesterol concentrations. J Nutr. 2006 Oct;136(10):2519-24. [PubMed:16988120 ]
  17. 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 ]
  18. Ma L, Lin XM: Effects of lutein and zeaxanthin on aspects of eye health. J Sci Food Agric. 2010 Jan 15;90(1):2-12. doi: 10.1002/jsfa.3785. [PubMed:20355006 ]
  19. Namitha KK, Negi PS: Chemistry and biotechnology of carotenoids. Crit Rev Food Sci Nutr. 2010 Sep;50(8):728-60. doi: 10.1080/10408398.2010.499811. [PubMed:20830634 ]