CHEBI:27547 - zeaxanthin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name zeaxanthin
ChEBI ID CHEBI:27547
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:10108, CHEBI:27361
Supplier Information ZINC000001532567
Download Molfile XML SDF
Wikipedia License
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.
Read full article at Wikipedia
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/h11-24,35-36,41-42H,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
InChIKey JKQXZKUSFCKOGQ-QAYBQHTQSA-N
SMILES CC(\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
Metabolite of Species Details
Oscillatoria sp. (NCBI:txid1159) CH2Cl2/MeOH(2:1) extract of assemblage of two cyanobacteria, Oscillatoria sp. and Hormoscilla sp. See: PubMed
Hormoscilla (NCBI:txid881023) CH2Cl2/MeOH(2:1) extract of assemblage of two cyanobacteria, Oscillatoria sp. and Hormoscilla sp. See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing zeaxanthin (CHEBI:27547) has parent hydride β-carotene (CHEBI:17579)
zeaxanthin (CHEBI:27547) has role antioxidant (CHEBI:22586)
zeaxanthin (CHEBI:27547) has role bacterial metabolite (CHEBI:76969)
zeaxanthin (CHEBI:27547) has role cofactor (CHEBI:23357)
zeaxanthin (CHEBI:27547) is a carotenol (CHEBI:23045)
Incoming zeaxanthin bis(β-D-glucoside) (CHEBI:63067) has functional parent zeaxanthin (CHEBI:27547)
IUPAC Name
(3R,3'R)-β,β-carotene-3,3'-diol
Synonyms Sources
(3R,3'R)-dihydroxy-β,β-carotene ChEBI
all-trans-β-carotene-3,3'-diol ChEBI
all-trans-zeaxanthin UniProt
anchovyxanthin ChEBI
β,β-carotene-3,3'-diol ChEBI
Zeaxanthin KEGG COMPOUND
Manual Xrefs Databases
C00000931 KNApSAcK
C06098 KEGG COMPOUND
CPD1F-130 MetaCyc
LMPR01070261 LIPID MAPS
Zeaxanthin Wikipedia
View more database links
Registry Numbers Types Sources
144-68-3 CAS Registry Number KEGG COMPOUND
144-68-3 CAS Registry Number ChemIDplus
2068416 Beilstein Registry Number Beilstein
Last Modified
25 July 2019