CHEBI:28838 - lutein

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name lutein
ChEBI ID CHEBI:28838
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43817, CHEBI:6576, CHEBI:27324
Supplier Information ZINC000001532567
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β-Carotene (beta-carotene) is an organic, strongly colored red-orange pigment abundant in fungi, plants, and fruits. It is a member of the carotenes, which are terpenoids (isoprenoids), synthesized biochemically from eight isoprene units and thus having 40 carbons. Dietary β-carotene is a provitamin A compound, converting in the body to retinol (vitamin A). In foods, it has rich content in carrots, pumpkin, spinach, and sweet potato. It is used as a dietary supplement and may be prescribed to treat erythropoietic protoporphyria, an inherited condition of sunlight sensitivity. β-carotene is the most common carotenoid in plants. When used as a food coloring, it has the E number E160a.: 119  The structure was deduced in 1930. Isolation of β-carotene from fruits abundant in carotenoids is commonly done using column chromatography. It is industrially extracted from richer sources such as the algae Dunaliella salina. The separation of β-carotene from the mixture of other carotenoids is based on the polarity of a compound. β-Carotene is a non-polar compound, so it is separated with a non-polar solvent such as hexane. Being highly conjugated, it is deeply colored, and as a hydrocarbon lacking functional groups, it is lipophilic.
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Formula C40H56O2
Net Charge 0
Average Mass 568.87144
Monoisotopic Mass 568.42803
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/h11-25,35-37,41-42H,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-/m0/s1
InChIKey KBPHJBAIARWVSC-RGZFRNHPSA-N
SMILES CC(\C=C\C=C(C)\C=C\[C@H]1C(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
Roles Classification
Biological Role(s): food colouring
A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): food colouring
A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199).
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ChEBI Ontology
Outgoing lutein (CHEBI:28838) has parent hydride (6'R)-β,ε-carotene (CHEBI:35147)
lutein (CHEBI:28838) has role food colouring (CHEBI:77182)
lutein (CHEBI:28838) has role plant metabolite (CHEBI:76924)
lutein (CHEBI:28838) is a carotenol (CHEBI:23045)
Incoming lutein 5,6-epoxide (CHEBI:27448) has functional parent lutein (CHEBI:28838)
IUPAC Name
(3R,3'R,6'R)-β,ε-carotene-3,3'-diol
Synonyms Sources
(3R,3'R,6S)-4,5-DIDEHYDRO-5,6-DIHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL PDBeChem
Bo-Xan ChemIDplus
E 161b ChEBI
Lutein KEGG COMPOUND
lutein UniProt
Xanthophyll KEGG COMPOUND
Manual Xrefs Databases
4145 DrugCentral
C00003776 KNApSAcK
C08601 KEGG COMPOUND
CPD1F-119 MetaCyc
DB00137 DrugBank
HMDB0003233 HMDB
LMPR01070274 LIPID MAPS
LUT PDBeChem
Lutein Wikipedia
View more database links
Registry Numbers Types Sources
127-40-2 CAS Registry Number KEGG COMPOUND
127-40-2 CAS Registry Number ChemIDplus
2068550 Reaxys Registry Number Reaxys
Citations Types Sources
10714278 PubMed citation Europe PMC
14670087 PubMed citation Europe PMC
23543147 PubMed citation Europe PMC
24451312 PubMed citation Europe PMC
Last Modified
22 February 2017