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Record Information
Version4.0
Creation Date2006-05-22 15:12:43 UTC
Update Date2017-09-21 20:38:39 UTC
HMDB IDHMDB0003233
Secondary Accession Numbers
  • HMDB03233
StatusDetected and Quantified
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 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 ).
Structure
Thumb
Synonyms
ValueSource
3,3'-Dihydroxy-alpha-caroteneHMDB
all-trans-(+)-XanthophyllHMDB
all-trans-LuteinHMDB
beta,epsilon-Carotene-3,3'-diolHMDB
bo-XanHMDB
Lutein esterHMDB
LuteineHMDB
trans-LuteinHMDB
Vegetable luteinHMDB
Vegetable luteolHMDB
Lutein FMeSH
Lutein gMeSH
Lutein, gammaMeSH
gamma LuteinMeSH
Chemical FormulaC40H56O2
Average Molecular Weight568.8714
Monoisotopic Molecular Weight568.428031036
IUPAC Name(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R)-4-hydroxy-2,6,6-trimethylcyclohex-2-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 Name(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R)-4-hydroxy-2,6,6-trimethylcyclohex-2-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
CAS Registry Number127-40-2
SMILES
O[C@@H]1CC(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]2C(C)=CC(O)CC2(C)C)C(C)(C)C1
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/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35?,36-,37+/m1/s1
InChI KeyKBPHJBAIARWVSC-RTIVXWJOSA-N
Chemical Taxonomy
DescriptionThis compound 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 DescriptorsNot Available
Ontology
Disposition
Biological Location:
Subcellular:
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point196 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000732 mg/mLALOGPS
logP8.29ALOGPS
logP8.55ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.22ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity195.06 m3·mol-1ChemAxon
Polarizability73.38 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
  • Adrenal Gland
  • Eye Lens
  • Fibroblasts
  • Gonads
  • Intestine
  • Lens
  • Neuron
  • Placenta
  • Retina
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.180 +/- 0.0800 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.200 +/- 0.100 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.180 +/- 0.0700 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.140 +/- 0.0500 uMAdult (>18 years old)Male
Normal
details
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
BiofluidStatusValueAgeSexConditionReferenceDetails
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 ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00137
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB015471
KNApSAcK IDC00003776
Chemspider ID4938343
KEGG Compound IDC08601
BioCyc IDCPD1F-119
BiGG IDNot Available
Wikipedia LinkLutein
NuGOwiki LinkHMDB0003233
METLIN ID3601
PubChem Compound6433159
PDB IDNot Available
ChEBI ID28838
References
Synthesis ReferenceNot Available
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. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  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 ]